School Science Lessons
Topic 16c
2024-06-18
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Plant oils
Table of contents
16.3.5.1a Aescin
16.3.2.0 Aldehydes
16.3.5.2 Amido phthalic acid
16.3.3.1 Ambrettolide
16.2.2.2 Apiole
16.2.2.4 Asarone
16.4.7.2 Bergenin
16.3.6.23 Caffeic acid
16.3.6.6 Camphor
16.2.2.5 Carpacin
16.3.6.4 Castor oil
16.3.10.3 Chavicol
16.2.2.7 Chevibetol
16.3.2.1 Chloral
16.3.6.9 Clove oil, eugenol
16.3.2.5 Cucumber aldehyde
16.3.2.2 Decanal
16.3.3.2 Diacetyl
16.2.2.8 Dillapiole
16.2.2.9 Elemicin
16.3.6.16 Ellagic acid
16.3.6.17 Geraniin
16.3.6.18 Chebulagic acid
16.3.5.3 Eosin
16.6.1 Essential oils
16.3.6.9 Eugenol
16.3.6.11 Eugenol acetate
16.6.2 Fixed oils
16.3.5.4 Fluorescein
16.3.5.0 Fluorescent liquids
16.3.6.19 Gallic acid
16.3.6.7 Gingerol
16.3.6.24 Isoeugenol
16.3.6.25 Isosafrole
16.3.10.1 Juglone
16.3.3.0 Ketones
16.3.10.6 Lawsone
16.3.5.6 Magdala red
16.3.10.5 Methyl eugenol
16.3.6.12 Methyl isoeugenol
16.3.3.3 Muscone
16.3.6.13 Myristicin
16.3.2.3 Nonanal
16.3.2.4 Nonenel
16.3.6.14 Nothoapiole
16.6.0 Oils, essential oils, fixed oils, vegetable oils
16.3.2.8 Oxidation of methanol to methanal
16.2.2.1 Phenylpropenes
16.3.10.2 Pindone
16.6.0 Plant oils, essential oils, fixed oils, vegetable oils
16.3.2.6 Prepare ethanal with potassium manganate (VII).
16.3.2.7 Prepare ethanal with potassium dichromate.
16.3.6.20 Propyl gallate
16.3.5.7 Quinine
16.3.10.0 Quinones
16.3.10.4 Safrole
16.4.7.1 Salicyclic acid
16.3.6.7 Shogaol
16.4.6.0 Tests for gases from burning hydrocarbons
16.6.3 Vegetable oils
16.3.6.7 Zingerone

16.3.3.0 Ketones
16.3.3.01 Ketones
16.3.3.2 Diacetyl
16.3.3.3 Muscone

16.6.0 Plant oils, essential oils, fixed oils, vegetable oils
16.6.1 Essential oils
16.6.1a List of essential oils
16.6.2 Fixed oils
16.6.2a List of fixed oils
16.6.3 Vegetable oils
16.6.3a List of vegetable oils
Alliin, Allyl disulfide, Asarinin, Diallyl disulfide

16.2.2.1 Phenylpropenes
Phenylpropenes, phenylpolypropanoids, allylbenzenes
Phenylpropenes have a propene substituent bound to a phenyl group.

16.2.2.2 Apiole
Apiole, C12H14O4, apioline, parsley apiole, parsley camphor, phenylpropene derivative, a benzodioxole, green crystals
It is used to treat menstrual disorders, and may be toxic in high doses causing liver and kidney damage.
It is reduced by steam from green oil of parsley.
It occurs in fennel, celery, parsley seeds, dill, cinnamon, Sassafras albidum, Matico (Piper angustifolium).

16.2.2.4 Asarone
Asarone, C12H16O3, is a phenylpropanoid, volatile fragrant oil, fungicide, bactericide, spasmolytic, anti-algal, animal carcinogen, insect attractant.
It occurs in Sweet flag.
Alpha-asarone (trans-isoasarone), occurs in carrot seed.
Beta-asarone, is antifungal, and occurs in Acoris bitters, but may be carcinogenic.
In Acorus calamus, (calamus oil banned in USA), Asarum europaeum, in Matico (Piper angustifolium).
See diagram: Asarone.

16.2.2.5 Carpacin
Carpacin, C11H12O3, is a phenylpropanoid, isosafrole methyl ether, insecticide, weakly sedative.
It occurs in Carpano tree, Cinnamon, (Cinnamomum verum), Lauraceae, in Prostrate justicia (Justicia prostrata).
It is used as a folk medicine as an antidepressant.

16.2.2.7 Chevibetol
Chevibetol, C10H12O2, is a phenylpropanoid, m-eugenol, occurs in Betel pepper.

16.2.2.8 Dillapiole
Dillapiole, C12H14O4, is a phenylpropanoid, benzodioxole and is related to Apiole.
It occurs in dill, fennel, coriander, Piper species, and in seeds of Bunium persicum (black caraway).

16.2.2.9 Elemicin
Elemicin, C12H16O3, is a phenylpropene, and occurs in carrot, elemi oil and nutmeg.
In Aniba, Boronia, Croton, Cymbopogon, Dalbergia, Melaleuca, Monopteryx.

16.3.2.0 Aldehydes
1.5 Aldehydes, List of aldehydes.
16.3.2.01 Aldehydes, alkanals.
Cinnamaldehyde
16.3.2.3 Nonanal.
16.3.2.2 Decenal.
Experiments.
9.3.7.2 Tests for oxidation of glucose, blue bottle experiment
16.3.2.8 Oxidation of methanol to methanal
16.3.2.7 Prepare ethanal with potassium dichromate
16.3.2.6 Prepare ethanal with potassium manganate (VII)
9.142.2 Tests for aldehydes with Fehling's solution
9.3.7.3 Tests for aldehydes, Tollens' test

16.3.6.4 Castor oil
Castor bean: 9.5.4.1
Castor oil bush: Ricinus communis.
Decanedioic acid:
Castor oil, Ricinoleic acid: 16.3.1.0
Saturated carboxylic acid, decanedioic acid, HOOC(CH2)8COOH, sebacic acid, from castor oil.
Castor oil experiments.
Albuminous seed, castor oil plant: 9.5.4.1
Butanedioic acid (succinic acid): 16.1.4
Castor oil drop : 19.3.24 (Physics)
Iron filings on the overhead projector: 29.2.2.12 (Physics)
Lectins: 16.3.17
Lipsticks: 19.7.2
Polyglycerol polyricinoleate (from mature castor plant): E476
Ricin:
Tests for lipase activity, castor oil, milk: 9.3.14 (Tests)
Viscosity and temperature: 17.3.13 (Physics)

16.3.5.0 Fluorescent liquids
Escalin
16.3.5.2 Amido phthalic acid
16.3.5.3 Eosin Y, bromoeosin
16.3.5.4 Fluorescein
16.3.5.6 Magdala red
16.3.5.7 Quinine
16.3.5.8 Safranin (safranine, safranin O)

16.3.1.0 Ricinoleic acid
Ricinoleic acid, C18H34O3, castor oil, ricinolic acid, ricinic acid, 2-hydroxyoctadec-9-enoic acid, Irritant.
(Greek castor beaver, because sacs in the groin contains substance similar to castor oil and formerly used to treat constipation).
Ricinus oil, a fixed oil, from Ricinus communis, Euphorbiaceae, castor oil bush, castor bean, castor oil plant, kikayon
Ricinine
Ricinus communis endosperm has aleurone grains and oil globules, fatty reserves as a liquid oil, mainly Ricinoleic acid, laxative, herbal remedy.
The fruit of the castor bean, Ricinus, suddenly split apart to throw out seeds.
Seeds contain | Ricin | a highly toxic protein, LD50 22 micrograms per kg.
It was used for warfare and poisoning prominent people.
1. Ricinoleic acid, 12-Hydroxy-cis-9-octadecenoic acid, 12-Hydroxyoleic acid, CAS Number 141-22-0, Molecular Weight 298.46, C17H32(OH)COOH,
CH3(CH2)5CH(OH)CH2CH=CH(CH2)7COOH
2. E476 Polyglycerol polyricinoleate, (polyglycerol esters of inter-esterified ricinoleic acid from mature castor plant) (emulsifier)
Saturated carboxylic acids, Decanedioic acid, HOOC(CH2)8COOH, sebacic acid, from castor oil
3. Castor beans contain two toxic proteins, so the castor plant is a poisoning hazard to children and pets.
A single castor bean seed may be fatal for a child if the seed masticated and chewed.
Ricin is a very toxic protein, because one milligram can kill a human adult.
Ricin may be both a chemical and biological weapon and is explicitly prohibited by the Biological and Toxin Weapons Convention, (BTWC).
4. RCA (Ricinus communis agglutinin) is a toxic protein that agglutinates red blood cells.
Injection of RCA into the bloodstream causes blood to coagulate.
Ingestion of a castor bean or its products will release Ricin, but the RCA cannot cross the intestinal wall.
Castor oil contains very little Ricin or RCA.

16.3.2.01 Aldehydes, alkanals
9.142.2 Tests for aldehydes with Fehling's solution
1. Aldehydes contain the group CH.O, -CHO, and are formed by partial oxidation of primary alcohols.
2. Name "aldehyde" from (Latin aldehyde dehydrogenated alcohols).
3. Names ending in (-al), alkanals, e.g. methanal (formaldehyde) CH2=O, HCHO, and ethanal (acetaldehyde) CH3CHO, the simplest aldehydes.
4. Aldehydes are compounds in the form RC(=O)H, a carbonyl group C=O is bonded to one hydrogen atom attached to the carbon atom and to one R group.
5. Aldehydes are reducing agents and can be detected with Tollens' test or Fehling's test.

16.3.2.1 Chloral
Chloral, CCl3CHO, chloral hydrate, trichloroacetaldehyde, trichlorethanal, harmful if ingested, Not permitted in schools
It is pungent volatile liquid, hypnotic used as its crystalline hydrate, chloral hydrate.
Chloral hydrate, Cl3CCH(OH)2, trichloroacetaldehyde hydrate, sedative, hypnotic, "prescription only" drug in Australia.
Tests for amylose and amylopectin: 9.132a

16.3.2.2 Decanal
Decanal, C10H20O, C9H19CHO, CH3(CH2)8CHO, decyl aldehyde, colourless, clear oily liquid, fragrance and flavouring agent.
It has a fatty or soapy smell, fatty or fried or citrus taste, and it breaks down on heating.
It occurs in coriander, orange peel, citrus, buckwheat

16.3.2.3 Nonanal
Nonanal, C9H18O, CH3(CH2)7CHO, nonanaldehyde, pelagonaldehyde, flavouring agent, colourless to pale yellow, oily liquid, in some perfumes
It has rose-orange waxy odour, citrus taste.
It occurs in rose and citrus oils and pine oils

16.3.2.4 Nonenel
Nonenel, C9H16O, 2-Nonenal, trans-2-nonenal (not noneal!), colourless liquid, aroma of aged beer, and occurs in buckwheat

16.3.2.5 Cucumber aldehyde
Cucumber aldehyde, C9H14O, violet leaf aldehyde, 2,6-nonadienal, flavour and fragrance agent, odour of violet leaf, green vegetable odour
It occurs in cereals, cherry, melon, peas, cooked potato, milk, fish, black tea, oyster, clam.
Cucumber aldehyde has cucumber smell, occurs in cucumber juice, and is used as flavouring agent.

16.3.2.6 Prepare ethanal with potassium manganate (VII)
Add one drop of 1% potassium manganate (VII) to five drops of ethanol and ten drops of dilute sulfuric acid.
Heat gently.
The purple colour disappears as potassium manganate (VII) solution is reduced to manganese (II) sulfate.
Note the odour of an acetaldehyde.
CH3CH2OH + (O) --> CH3CHO + H2O
2KMnO4 + 3H2SO4 + 5CH3CH2OH --> K2SO4 + 2MnSO4 + 8H2O + 5CH3CHO

16.3.2.7 Prepare ethanal with potassium dichromate.
Add two drops of 0.1 M potassium dichromate solution to two drops of ethanol and ten drops of dilute sulfuric acid.
Heat gently.
The orange potassium dichromate solution turns green showing the presence of Cr3+.
The reaction forms ethanal then ethanoic acid (acetic acid).
Note the odour of an acetaldehyde.
C2H5OH + (O) --> CH3CHO + H2O
ethanol + (oxygen) --> ethanal + water
CH3CHO + (O) --> CH3COOH
ethanal + (oxygen) --> ethanoic acid
K2Cr2O7 + 4H2SO4 + 3CH3CH2OH --> K2SO4 + Cr2(SO4)3 + 7H2O + 3CH3CHO

16.3.2.8 Oxidation of methanol to methanal
Oxidation of methanol to methanal, platinum catalyst
See diagram 16.3.3: Oxidation of methanol
Be careful! This experiment may be too dangerous for a school science laboratory.
Test the experiment in the science preparation room before demonstrating it in the classroom.
Do not let anyone look down into the flask if the experiment appears not to be working!.
Put 10 mL methanol in a flask and heat briefly with a Bunsen burner.
Heat a piece of platinum wire connected to a copper wire until it is red hot.
Hook a copper / platinum wire inside the flask to start the reaction.
Heat the wire again if the reaction does not start.
The reaction continues till all the MeOH is used up.
To stop the reaction, remove the catalyst platinum wire catalyst.
Be careful!.
Methanol is oxidized to methanal when the vapour reaches a certain concentration with a loud "whoosh" sound as the vapour burn and leaves the flask.
The copper T-piece acts as a chimney allowing entry of air when the vapour bums.
The Pt wire changes from red-hot to silver.
CH3OH + O2 --> CH2O + H2 (Pt catalyst).
CH2O + O2 --> CO2 + H2O (Pt catalyst).

16.3.3.01 Ketones
Ketones =CO (-one), e.g. propanone, (acetone). CH3C=OCH3
9.142.2 Tests for aldehydes with Fehling's solution
Ketones have a carbonyl group C=O, bonded to two carbon atoms in the form R2C=O, but neither R may be H.
Ketones contain the ketone group -CO-.
It is a carbonyl group with two single bonds to other carbon atoms.
Propanone (acetone, CH3COCH3, and butanone CH3COC2H5, methyl ethyl ketone), are the simplest saturated ketones (R1COR2).
Ketone names end with "-oneH">
Ketones cannot be detected with Tollens' test or Fehling's test.

16.3.3.1 Ambrettolide
Ambrettolide, C16H28O2, isoambrettolide, a macrocyclic musk, flavour and fragrance agent, colourless to pale yellow liquid
It has a sweet soapy musk odour and taste, and is used as a food additive.

16.3.3.2 Diacetyl
Diacetyl, CH3COCOCH3, butanedione, dimethyldiketone
It is used in the popcorn industry to give a butter or butterscotch flavour and creamy odour to popcorn sold in bags.
Workers in the popcorn industry have reported medical problems with their respiratory systems, particularly the lungs, leading to workers' compensation.
Heating bags of popcorn in a microwave oven may cause similar problems.
The popcorn industry is considering not using diacetyl in bagged products.

16.3.3.3 Muscone
Muscone, C16H3O, methylcyclopentadecanone, musky smell, flavouring ingredient, perfume fixative, musk from musk deer, but is now produced artificially.

16.3.5.1a Aescin, escin
Aescin, escin, C55H86O24, pentacyclic triterpenoid saponin, the main saponin of more than 30 different saponins.
It occurs in seeds of Aesculus.
It is used to treat blood vessel disorders, reduce inflammation, oedema, pain, inhibits edema, treats vascular fragility.
Horse chestnut, (Aesculus hippocastanum), leaves.
See diagram: Aescin.

16.3.5.2 Amido phthalic acid
Amido phthalic acid, C14H10BrNO3, amido-tarephthalic acid, 4-aminophthalic acid
It gives pale violet colour by reflected light and pale yellow colour by transmitted light.
Amido-tarephthalic acid gives bright green colour by reflected light and pale green colour by transmitted light.

16.3.5.3 Eosin
Eosin, C20H6Br4Na2O5, Eosin Y, bromoeosin, tetrabromofluorescein, Solvent Red 43, Japan red 223, red fluorescent dye
Eosin, eosine, bromoeosin, gives yellow green colour by reflected light and orange colour by transmitted light.
It is formed by reaction of bromine with fluorescein, the potassium salt of tetrabromo-fluorescein, sodium-2,4,5,7-tetrabromofluorescein.
Eosin Y has yellowish colour, and Eosin B (Acid red), has bluish colour.
It is used as a counter stain to hematoxylin for microscopic examination.
Eosin, an acidic dye, stains cytoplasm stained orange pink and haematoxylin, a basic dye, stains nuclei blue or purple where nucleic acids occur.
Eosin stains red blood cells intensely red.

16.3.5.4 Fluorescein
Fluorescein, C20H12O51, 3-dihydoxybenzene phthalein, 2-(6-hydroxy-3-oxo-xanthen-9-yl)
Fluorescein, gives intense green colour by reflected light and orange yellow colour by transmitted light.
The red crystals that can dissolve in alkali to form a red colour and green fluorescence.
See: 1.5: Prepare fluorescein solution.
See diagram: Fluorescein.

16.3.5.6 Magdala red
Magdala red, C30H20N3+, phloxine B (tetrabromotetrachloro-fluorescein), acid red 92
It gives opaque scarlet colour by reflected light and brilliant carmine colour by transmitted light.
It is used to identify unhealthy yeast cells.

16.3.5.7 Quinine, C20H24N2O2
Quinoline Alkaloid
See diagram: Quinine.
Quinine is an antimalarial, antipyretic, gives a pale blue colour by reflected light and no colour by transmitted light.
It is extracted from the bark of Cinchona ledgeriana (quinine tree, "fever tree"), and Remijia in South America.
It was formerly an anti-malarial medicine and is still used for treatment of some heart conditions.
As a medicine it was taken in carbonated mineral water, but nowadays is still taken as a beverage called "tonic water".
Commercial tonic water, is valued for the slightly bitter taste of "gin and tonic", but tonic water is not a medicine.
Quinine must be identified on the label of commercial products containing it, because some people are hypersensitive to quinine.
Cinchona was discovered in the 1630s as a treatment for malaria and was the only effective cure known in Europe until synthetic replacements in the 1940s.
Malaria remains today one of the deadliest diseases known throughout the tropics, and until the 20th century the disease was prevalent throughout Europe.
The Cinchona tree is native to the eastern slopes of the Andes, across Ecuador, Peru and Bolivia, so inaccessible for most Europeans during the 17th century.
In the 18th and 19th centuries, demand outstriped supply and threats of overharvesting and the desire to control the source caused empires to source this plant.
The Spanish tried to prevent this access, but failed to establish their own successful plantations.
The Dutch, in Indonesia, and the British, in India, founded government controlled plantations for mass production of quinine.

16.3.5.8 Fluorescence spectroscopy of quinine
Fluorescence spectroscopy can be used to determine the percentage quinine content in samples of tonic water or bitter lemon It compares fluorescence of sample in UV light to the fluorescence of quinine sulfate solution containing 10 mg of quinine sulfate in 1L of deionized water.
Large doses of quinine may cause heart problems, but small doses in a small bottle of tonic water have been effective in treating leg muscle cramps.
The quinine alkaloid, C20H24N2O2.3H2O, was first extracted from the bark of Cinchona officinalis, Rubiaceae.
Common names include quinine bark, China bark, Peruvian bark, Jesuit's bark, fever tree.
Cinchona ledgeriana and C. succirubra produce the highest quantity of quinine alkaloids, but now mostly synthetic quinine dihydrochloride monohydrate.
Benzoquinone, C6H4O2, para-quinine, cyclohexadiene-1,4-dione, occurs in coal smoke.
Quinidine, antiarrhythmic, in quinine tree Cinchona ledgeriana.
Amines and alkaloids: 16.0.0 Amines and alkaloids.
Poisons and First Aid: 3.10.0 (Table).
Quinine hemisulfate monohydrate and dihydrate, Quinine hydrochloride dihydrate, Quinine sulfate.

Quinine experiments Quinine bitter taste experiment - replace quinine with cold tea solution and note the difference in taste.
Quinine iodosulfate, Dichroic polarization colours: 27.82
Sense of taste, the gustatory system: 9.246
Taste, smell, flavour: 19.3.1

16.3.6.6 Camphor, C10H16O
Camphor, bicyclic monoterpene ketone, DL-Camphor, colourless to white crystalline powder, "mothball" odour.
It is skin antipruritic, anti-infective, moth-proofing safer alternative to naphthalene and 1,4-dichlorobenzene mothballs.
Cinnamon, (Cinnamomum verum), Lauraceae
Natural camphor was distilled from the clippings, wood and roots of the Camphor laurel tree, (Cinnamomum camphora), camphor laurel tree.
Nowadays camphor is a synthetic aromatic, produced from vinyl chloride and cyclopentadiene.
Camphor is a crystalline terpenic ketone, complex chemical composition, highly flammable, harmful if ingested.
DL-camphor is natural camphor.
Camphor oil | Borneol | Camphene | Carvacrol | Cineole | Citronellol |.
Do not inhale hot fumes of camphor, because the terpenic ketone camphor can be highly toxic.
Camphor types:
Brown camphor contains Safrole and Terpineol.
White camphor contains Cineole and Pinene, but not Safrole.
Yellow camphor contains Safrole and sesquiterpenes |.
Camphor is used as a topical rubefacient / counter-irritant medication.
It is a common ingredient of anti-itch and heat-rub medicines, e.g. Haw Par Tiger Balm.
Camphor, Rubefacient, Cinnamomum camphora (camphor tree), harmful if ingested.
Camphor repels clothes' moths and cats and is used to make gunpowder and celluloid.
Celluloid is cellulose nitrate plasticized with camphor.
Use D-Camphor instead of naphthalene moth balls to protect clothes from moths and silverfish.
Camphor experiments
Prepare camphor oil: 19.6.7
Prepare thionyl chloride, SOCl2: 12.18.3.2
Drive a boat with surface tension, camphor boat, spinning dancers: 19.1.3
Terpenes C10H16: Terpenes

16.3.6.7 Gingerol, C17H26O4
Gingerol, 6-Gingerol, 8-Gingerol, 10-Gingerol, 12-Gingerol
6-gingerol in ginger rhizome, a phenol, yellow oil, antioxidant, anti-inflammatory, antitumour, anti-nausea, anti-carcinogenic.
6-gingerol, C17H26O4 --> zingerone, vanillyl acetone, C11H14O3.
Te 6-, 8-, 10-, 12- gingerols are easily altered by cooking or drying.
Cooked ginger is less pungent than fresh ginger, gingerols --> zingerones.
Dried ginger is more pungent than fresh ginger, gingerols --> shogaols, 6-gingerol, C17H26O4 --> 6-shogaol, C17H24O3.
Ginger rhizome: Ginger, (Zingiber officinale), Zingiberaceae
See diagram: Gingerol.
Zingerone, C11H14O3, Vanillylacetone, a methyl ketone, is the pungent principle of ginger, only slightly pungent, sweet spicy aroma.
It is used in imitation fruit flavours, ginger beer, ginger ale, gingerbread.
It occurs in fruits, e.g. cranberry, raspberry, mango, Alpinia officinarum and Vitis vinifera .
16.3.6.9 Clove oil, eugenol, C10H12O2
Oil of cloves, eugenol, 2-methoxy-4-(2-propenyl) phenol, an allyl benzene produced from dried flower buds.
It contains a high concentration of antioxidants.
I is used as a spice, fish killer, to repels ants, and a herbicide.
Oil of cloves is toxic at low concentrations, and harmful if large quantity is ingested.
The relative density is 1.04 -1.06, so it does not float on water.
Clove oil contains eugenol and caryophyllene from (Eugenia caryophyllus)
It occurs in essential oils, e.g. cinnamon, clove oil, pimento, nutmeg, bay leaf.
It is an analgesic and antiseptic.
It is used in dentistry for its main ingredient eugenol, home remedy for toothache, in Indonesian clove and tobacco cigarettes, inhibit mould, cooking ingredient.
It has a pleasant, spicy, clove-like odour and taste, but will darken and thicken when exposed to air, slightly soluble in water.
It is used in perfume, flavourings, medicine, local antiseptic and anaesthetic in dentistry.
Eugenol may cause liver damage and some people are allergic to it.
Formerly it was used in the production of isoeugenol for the manufacture of Vanillin
See diagram: Eugenol.

16.3.6.11 Eugenol acetate
Eugenol acetate, C12H14O3, eugenyl acetate, acetyl eugenol, is colourless to pale yellow, flavouring agent, floral flavour, spicy odour.
It occurs in clove oil, caraway, cinnamon leaf.

16.3.6.12 Methyl isoeugenol
Methyl isoeugenol, C11H14O2, phenylpropene, may cause allergic skin reaction.

16.3.6.13 Myristicin
Myristicin, C11H12O3, phenylpropene occurs in clove oil, caraway, cinnamon leaf, nutmeg essential oil.
Myristic acid, Tetradecanoic acid, C14H28O2, saturated long-chain fatty acid, straight-chain saturated fatty acid, oily white crystalline solid.
It occurs in palm oil, coconut oil, and butter fat.

16.3.6.14 Nothiapole
Nothiapole, C13H16O5, phenylpropene, occurs in perilla, (Perilla frutescens), Lamiaceae

16.3.6.16 Ellagic acid, C14H6O8
Ellagic acid is derived from hydrolysis of tannins, and is an antioxidant, antiproliferative, dietary supplement.
It occurs in oak trees and foods, e.g. walnuts.

16.3.6.17 Geraniin, C41H28O27
Geraniin, a tannin dehydroellagitannin, folk medicine, antidiarrheic drug, causes apoptosis in human melanoma cells.
It occurs in Nephelium lappaceum (rambutan) rind, in Geranium thunbergii.

16.3.6.18 Chebulagic acid, C41H30O27
Chebulagic acid, benzopyran tannin, antioxidant, immunosuppressive, hepatoprotective, alpha-glucosidase inhibitor
It is used against Staphylococcus aureus and Candida albicans.
It occurs in Terminalia species.

16.3.6.19 Gallic acid, C7H6O5
Gallic acid, C6H2(OH)3COOH, C7H6O5, (3,4,5-Trihydroxybenzoic acid), a water-soluble phenolic acid, colourless, yellow, crystalline compound, astringent, toxic if ingested, antioxidant, antineoplastic, apoptosis inducer, anticarcinogenic, anti-inflammatory, anti-fungal, anti-viral, found free and as part of tannins.
It is used in the pharmaceutical industry, used to synthesize mescaline (3,4,5-trimethoxyphenethylamine), used in photography, analytical reagent.
It occurs in oak bark, gall nuts, rhus, witch hazel, tea plant.
Gallic acid is formed by fermentation of tannic acid in nature.
Gallates are salts and esters of gallic acid.
The esters and polyesters of gallic acid are very widely distributed in angiosperms, as gallotannins, tannins, catechin gallates, aliphatic gallates, and have similar properties to gallic acid.
Dodecyl gallate, E312, (ester of gallic acid) (antioxidant) (Health risk, allergic reactions, hyperactivity) from esterification of lauryl alcohol and gallic acid.
Octyl gallate, E311, (synthetic salt of gallic acid) (antioxidant) (Health risk, allergic reactions).
See diagram: Gallic acid

16.3.6.20 Propyl gallate, C10H12O5
Propyl gallate, propyl 3,4,5-trihydroxybenzoate, ester from condensation of gallic acid and propanol, food additive E310, radical scavenger functions, white to creamy-white crystalline powder, odourless or faint odour, insoluble in water, slightly bitter taste, antioxidant added to foods containing oils and fats to prevent oxidation.
It occurs in maize, vegetable oils, animal fats.
Propyl gallate, antioxidants: See diagram 19.2.1.6
Propyl gallate, anti-fade reagent reduces photobleaching of fluorescence microscopy probes, e.g. fluorescein.

16.3.6.23 Caffeic acid, C9H8O4
Caffeic acid, C9H8O4 (HO)2C6H3CH=CHCO2H, (3, 4-dihydroxycinnamic acid), antioxidant, anti-inflammatory.
It occurs in: Achillea, Anthemis, Coffea, Cinchona, Conium, Digitalia, Papaver, Populus, Solanum, Taraxacum, burdock, hawthorn, artichoke, pear, basil thyme, oregano, apple.
Caffeic acid 3-glucosidem (C15H18O9), hydroxycinnamic acid, monosaccharide derivative, beta-D-glucoside

16.3.6.24a Isoeugenol, C10H12O2
Isoeugenol, phenylpropanoid, 4-propenylguaicol, related to phenylpropene, clear to pale yellow oily liquid, extracted from clove oil and cinnamon oil, slightly soluble in water, spicy odour and taste of cloves, prepared from eugenol by heating.
It is used in perfumes, flavourings, local antiseptic and analgesic, used to make Vanillin
Eugenol derivatives or methoxyphenol derivatives used in perfumers and flavourings, insect attractants, UV absorbers, analgesics, biocides and antiseptics, stabilizers and antioxidants for plastics and rubbers.
It occurs in Ylang ylang essential oil, nutmeg fruit, Rocky Mountain juniper, (Juniperus scopulorum) pine needles.

16.3.6.25 Isoafrole, C10H10O2
Isoafrole, phenylpropanoid, related to phenylpropene, colourless fragrant liquid, anise odour of anise.
It is used to make heliotropin and in oriental perfumes, e.g. Safrole, herbal remedy used for liver regeneration, but is a moderate poison.
It occurs in root beer, sarsaparilla flavours, ylang ylang essential oil, (Ligusticum acutiloba) essential oil, curry tree (Murraya koenigii) leaves.

16.3.10.0 Quinone, C6H4O2
Quinones, quinone, hydroquinone, juglone, See diagram 16.1.4.3: Quinones | See diagram 16.3.5.0: Quinones, Pindone sodium salt.
1. The chemical called "quinone" usually refers to the simplest quinone, the yellow crystalline molecule, C6H4O2, 1,4-benzoquinone, p -benzoquinone, para-quinine, para-quinone, cyclohexadiene-1,4-dione.
It is used for preparing dyes, tanning hides, and photography, bright yellow crystals.
It occurs in coal and tobacco smoke, in Iris kemaonensis.
2. Quinones contain the C=O groups in an unsaturated ring, as 1,2-quinones and 1,4-quinones (e.g. cyclohexandiene-1,4-dione), cyclic dione structure, conjugated diketones, e.g. benzoquinone, by conversion of -CH= groups into -C(=O)- groups.
3. Quinones are aromatic compounds in plants.
All quinones are coloured, many are plant pigments, e.g. lawsone from Lawsonia inermis the orange dye henna, and juglone from walnut shells, Juglans regia.
4. Quinones are formed from oxidation of hydroquinone and in pecan nuts, and are used in dyes.
5. Quinones are phenolics, polyphenols, e.g. Benzoquinones, Naphthoquinones, Anthraquinones.
6. Quinones occur in Aloe-emodin, Alkannin, Chrysophanol, Emodin, Juglone, Physcion, Primin, Plastoquinine-9, Ubiquinone-10.

Hydroquinone, C6H4(OH)2
Hydroquinone, hydroquinol, 1,4-dihydroxybenzene, 1,4-benzenediol quinol, is toxic if ingested.
Hydroquinone, benzene-1,4-diol, quinol, Solution < 25% Not hazardous.
It is used in photography developers and in skin whitening compounds to reduce colour of skin.
It occurs in coenzymes in animal and plant cells, and plastoquinones involved in photosynthesis, and vitamin K,

16.3.10.1 Juglone, C10H6O
Juglone, 1,4-napthoquinone, C.I. Natural brown 7, C.I. 7550.
It is produced by some trees in the walnut family, e.g. black walnut, Persian walnut, butternut, and pecan, and is leached or released into the soil.
Juglone has fungicide and insecticide properties, but it is toxic to many plant species.
Juglans regia, walnut tree, common walnut, English walnut, Persian walnut, the quinone juglone, walnut shells, oxidation of hydroquinone, Juglandaceae.

16.3.10.2 Pindone, C14H14O3
Pindone, C14H14O3, (ISO 1750) (2-pivaloylindan-1,3-dione).
It is an anticoagulant drug used to control rodents and rabbits, e.g. "Bunnybait" is 0.5 g / kg sodium salt of pindone is used as an oat bait for rabbits, C14H13NaO3.
See diagram 16.3.5.0: Quinones, Pindone sodium salt.

16.3.10.3 Chavicol, C9H10O
Chavicol, C9H10O, p-allylphenol, a phenylpropene, occurs in betel oil from (Areca catechu), the betel nut palm.

16.3.10.4 Safrole, C10H10O2
Safrole, a phenylpropene, colourless-yellow oil, aroma of "sweet shops", a heptocarcinogen that cause permanent liver damage.
Safrole is a genotoxic compound.
It occurs in root of Sassafras tree (Sassafras albidum), Brazilian sassafras (Octea odorifera), and quid of Betel leaf, (Piper sarmentosum), Piperaceae
Safrole-DNA adducts, which induce chromosomal variations.
It is found in oral cancers of Areca users.
Safrole is the principle constituent of sassafras oil and brown camphor oil.

16.3.10.5 Methyl eugenol, C11H14O2
Methyl eugenol, allylveratrol, methyl ether of eugenol.

16.3.10.6 Lawsone, C10H6O3
Lawsone, (2-Hydroxynaphthoquinone), hennotannic acid, yellow powder, protective agent, antifungal agent, ultraviolet filter.
It is used for synthesis of biologically active compounds, as a dye and in cosmetics - the principle constituent of the ancient dye "henna", (Bible, Song of Solomon 1:14 "cluster of henna blossoms").
It occurs in leaves of (Lawsonia inermis) henna, and in the flower (EicHornia crassipes) water hyacinth.
Experiment: Kill black mould.
Grow mould on bread and place a few drops of a solution of it on a nutrient agar plate and then incubate it.
Measure the size of the colony after a few days and then place a square of filter paper on the agar with various amounts of clove oil added and note the growth over the next week.
A solution of 2.5 mL of clove oil to 1 litre of water should kill the spores 24 to 48 hours.
Grow moulds at different concentrations of clove oil, from zero to 100% oil.

16.4.6.0 Tests for gases from burning hydrocarbons.
Hydrocarbons burn in excess air to form carbon dioxide and water.
The reaction is exothermic.
Methane burns with a clear flame.
Ethene (ethylene) and ethyne (acetylene) burn with a smoky luminous flame.
This flame can be seen above a chimney at many petrol refineries where excess ethene is burned off.
Experiment: Tests for gases from burning hydrocarbons
Light a natural gas burner or pour drops of cigarette lighter fuel in an evaporating basin and ignite it.
Hold a dry test-tube containing ice over the burning gas.
Water from the combustion condenses on the test-tube.
Add limewater and shake.
The milky precipitate shows the presence of carbon dioxide.
CH4 (g) + 2O2 (g) ---> CO2 (g) + 2H2O (g).
In insufficient oxygen, the poisonous gas carbon monoxide forms.
2CH4 (g) + 3O2 (g) ---> 2CO (g) + 4H2O (g).

16.4.7.1 Salicyclic acid, C7H6O3
Salicyclic acid, C7H6O3, HOC6H4COOH, hydroxybenzoic acid C7H6O3, [C6-C1], 2-Hydroxybenzoic acid, harmful, skin irritant.
Salicyclic acid is a bitter-tasting derivative of phenol, used to make fungicides and Aspirin, acetylsalicyclic acid.

16.4.7.2 Bergenin, C14H16O9
Bergenin, cuscutin (a trihydroxybenzoic acid glycoside), antitussive, anti-inflammatory, protects against liver disorders.
It occurs in Bergenia species, and in (Ardisia japonica).

16.6.1 Essential oils, volatile oils, ethereal oils.
Essential oils are not really "oils", i.e. not smooth, sticky liquids, immiscible in water, but are volatile oils obtained by distillation and having the characteristic odour of the plant from which it is extracted.
A "note" is a term used in perfumery, meaning any of the basic components of a fragrance of a perfume which give it its character.
Reference: The Encyclopedia of Essential Oils, by Julia Lawless, Thorsons, Harper Collins, 2002, ISBN 0 00 7145187.
1. An essential oil is a concentrated, hydrophobic liquid that volatilizes on heating without decomposition to form the distinctive scents of plants.
Essential oils are used in aromatherapy and in religious ceremonies requiring the burning of incense.
2. They are usually liquid, but may be solid, e.g. orris, or semi-solid, e.g. rose.
3. On exposure to air, they do not harden, but, unlike fixed oils, evaporate, leaving no oily residue.
4. They dissolve in alcohol, fats and oils, but not in water.
5. They are mainly volatile mixtures of terpenes and terpenoids, but also may contain esters, aliphatic and aromatic esters, phenolics and substituted hydrocarbons formed in plant oil glands.
6. Essential oils are not recommended for pregnant women.
7. For consumption recipes, buy only top quality essential oils from a reputable source.
Buy "Therapeutic" grade or "Food Grade" and never buy perfume grade or diluted or solvent extracted essential oils.
8. Essential oils include rose oil, jasmine oil, oil of cloves, lavender oil, peppermint oil, eucalyptus oil, ylang-ylang oil (Cananga odorata), and the cheap citrus oils, e.g. lemon oil, sweet orange oil.
They are extracted by distillation, expression and solvent extraction.
They cause plant odours, some of which can be distilled to form perfumes, cosmetics, bath products, flavouring food and drink flavourings, incense scents and substances that deter insects and herbivores
from damage or grazing.
9. Volatile oils.
An essential oil is usually regarded as a volatile oil produced by distillation with the odour characteristic of the distilled plant material.
However, the term is often used loosely in the herbalist and aromatherapy industries to describe any usually aromatic extracts from plant material.
10. Extraction.
Plant material --> (distillation) --> "distilled essential oilsH">
Plant material --> (expression, i.e. pressing and squeezing) --> "citrus oilsH">
Plant material --> (solvent extraction) --> "concretes" --> "absolutesH">
Plant material --> (solvent extraction) --> "resinoidsH">
Plant material --> ("enfleurage") --> "pomades --> "enfleurage absolutesH">
Concretes.
The "concretes" are extracted from raw previously-living plant material with hydrocarbon solvents, not steam distillation, and are usually about 50% wax and 50% volatile oil, e.g. jasmine.
The oil ylang ylang is 20% wax and 80% essential oil.
The term "concretes" may refer to the fact that they are more concentrated and stable than distilled essential oils.
Resinoids.
The "resinoids " are extracted from dead resinous material with hydrocarbon solvents to produce balsams, resins, oleoresins, oleo gum resins.
Absolutes.
The "absolutes" are extracted from the "concretes" by further solvent extraction using "absolute alcohol" (pure ethanol) to remove most of the wax.
Nowadays more pure "absolutes" are produced with liquid carbon dioxide.
Pomades.
The "pomades" were once produced by pressing cut flowers onto a glass plate covered with odourless fat, a process called "enfleurageH">
The volatile oils from the flowers that had diffused into the fat were extracted with alcohol to produce "enfleurage absolutesH">
Nature identical.
The pharmacy industry can produce most essential oils 96% synthetically, labelling them "nature identical" products.
However, the 4% of natural constituents may be important to the herbalist and aromatherapy.

16.6.1a List of essential oils.
HPLC
Agar oil, (Aquilaria malaccensis), oodh, Thymelaeaceae.
Ajwain oil, (Trachyspermum ammi), Thymol, Apiaceae.
Allspice oil, (Pimenta dioica), Myrtaceae.
Almond oil, (Prunus amygdalus), Rosaceae
Angelica root oil, (Angelica archangelica), Apiaceae.
Anise oil, (Pimpinella anisum), licorice odour, Apiaceae.
Asafoetida oil, (Ferula assafoetida), to flavour food, Apiaceae.
(Abies balsama), balsam fir needle oil, Pinaceae.
(Abies alba), silver fir oil, Pinaceae
(Pseudotsuga menziesii), Douglas fir oil, Pinaceae
Lemon balm oil, (Melissa officinalis), Lamiaceae.
Balm of Gilead oil, (Commiphora gileadensis), Burseraceae.
Balsum of Peru oil, (Myroxylon balsamum), flavour food and drink, Fabaceae.
Balsam torchwood, (Amyris balsamifera), Rutaceae.
Basil oil, (Ocimum basilicum), make perfumes, aromatherapy, Lamiaceae.
Bay oil, (Laurus nobilis), make perfumes, aromatherapy, Lauraceae.
Benzoin balsamic resin oil, (Styrax benzoin), Styracaceae.
Bergamot oil, (Citrus x aurantium subsp. bergamia, make perfumes, aromatherapy, Rutaceae.
Birch oil, oil of wintergreen, (Betula lenta), aromatherapy, Betulaceae.
Black pepper oil, (Piper nigrum), distilled from berries, Piperaceae.
Bois de rose oil, rosewood oil (Aniba rosaeodora), Lauraceae.
Borage seed oil, (Borago officinalis), Boraginaceae.
Borage oil, Borago officinalis seeds, anti-inflammatory, highest source of γ-linoleic acid.
Boldo oil, (Peumus boldus).
Boronia oil, absolute oil (Boronia megastigma), Rutaceae.
Buchu oil, (Agathosma betulina), buchu shrub, toxic | Diosphenol | Rutaceae.
Cade oil, Juniperus oxycedrus, contains | Cadinene | Cadinol | Guaiacol | distilled from wood, dark, aromatic, smoky smell.
It is used in cosmetics, incense, folk medicine, skin ailments, allergic reactions possible.
Cajeput oil, contains | Cineole, | Terpineol | Pinene | Nerolidol | distilled from leaves of Melaleuca cajuputi.
Catmint oil Calamint, (Calamintha sylvatica), Lamiaceae, cat mint, contains | Citral | Nerol | Citronellol | Limonene | Geraniol | Metatabilacetone | attracts cats.
Calamus oil, from Acorus calamus, contains | beta-asarone |Eugenol | banned in USA.
Calendula oil, marigold oil.
Camphor oil:
16.3.6.6
Camphor of Borneo oil.
Cananga oil | Caryophyllene | Safrole | Methyl salicylate |.
Capers (Capparis spinosa), Capparaceae | Carvone |.
Cannabis flower oil, essential oil, food flavouring.
Caraway seed oil, contains carvone terpenoid and has its taste, carveol, food flavouring.
Cardamom, (Elattaria cardamomum), Zingiberaceae, contains | Terpinyl acetate | Cineole |.
Carrot seed oil | Pinene | Daucol C15H26O2, an oxane C5H10O | carotol | Geraniol | Caryophyllene |.
It is used in aromatherapy.
Cascarilla bark oil, contains cymene, diterpene, Cassia, contains cinnamic aldehyde, methyl eugenol (dark brown liquid).
Cassie oil, contains | Benzyl alcohol | Methyl salicylate | Fernesol | Geraniol |.
Cabreuva oil, contains | Nerolidol |.
Calamansi oil.
Calamus oil, Calamus
Camphor oil, perfume, food additive, 16.3.6.6 Camphor oil.
Canada balsam
Cannabis flower oil.
17.1 Capsaicin oil (Capsicum oil) species.
Caraway, (Carum carvi), Apiaceae
Cardamom, (Elattaria cardamomum), Zingiberaceae
Carrot seed oil.
Cedarwood oil, cedar oil, perfumes.
Cedarwood, Atlas Cedarwood | atlantone | Caryophellene |.
Cedarwood, Texas Cedarwood | cedrene | cedrol|.
Cedarwood, Virginian Cedarwood | cedrene | cedrol |.
Celery seed oil (Apium graveolens var. dulce), Apiaceae.
contains Limonene
Chamomile oil (Matricaria chamomilla), Asteraceae.
Roman and German chamomile oil, azulene.
German Chamomile, contains Chamazulene, C14H16 (a product of distillation), Farnesene
Roman Chamomile, contains angelic acid esters | Tiglic acid | Pinene | Nerolidol | Cineole | Farnesol
Chervil (Anthriscus cerefolium), Apiaceae.
contains methyl chavicol, aromatic unsaturated ether, anethole, anise camphor.
Chilli pepper, Chillies, (Capsicum frutescens), Solanaceae.
Cinnamon, (Cinnamomum verum), inner bark for cinnamon sticks (cinnamon leaf oil contains |16.3.6.10 Eugenol.
| cinnamaldehyde | benzyl benzoate) (cinnamon bark oil contains | cinnamaldehyde |16.3.6.10 Eugenol | benzyl benzaldehyde| Pinene |.
It occurs in Coca Cola.
Cistus oil, Cistus labdanum, essential oil for aromatherapy, Cistaceae.
Citron oil (Citrus medica), Ayurvedic aromatherapy, Rutaceae.
Citronella grass, (Cymbopogon nardus), lemon grass oil, insect repellent, Poaceae.
Clove oil, (Syzygium aromaticum), Myrtaceae
Clove oil,16.3.6.10 Eugenol, Kills black mould: 16.3.6.9
Clove, (Syzygium aromaticum), Myrtaceae
Clary sage oil, Salvia sclarea, ancient essential oil, perfume, flavouring, aromatherapy, Lamiaceae.
Coconut oil (Cocos nucifera), food, skin and hair, Arecaceae.
Coffee oil, (Caffea arabica), Rubiaceae
Coriander oil, (Coriandrum sativum), Apiaceae
| Linalool | Borneol | Geraniol | Carvone | Anethole | Apiaceae.
It occurs in Chartreuse and Benedictine liqueurs.
Costmary oil, (Tanacetum balsamita), Asteraceae
Costus root oil, contains sesquiterpene lactones, e.g. dihyrocostus lactone, cartophyllene, Costaceae.
Cranberry oil, large cranberry, (Vaccinium macrocarpon), Ericaceae
Contain high omega-3 and omega-6 fatty acids.
Cubeb oil, tailed pepper to flavour foods, Piper cubeba, Tailed pepper oil
Cubeb oil, contains sesquiterpenes, monoterpenes (treats amoebic dysentery), flavour foods.
Cumin oil, (Cuminum cyminum), contains aldehydes | Cuminaldehyde | Pinene | farnesine | Caryophellene |.
Cypress oil, contains | Pinene | Camphene | used for cosmetics.
Cypriol oil.
Curry leaf oil (Murraya koenigii), Rutaceae.
contains alcohols | d-Borneol | Pinene | Camphene | used to flavour food.
Davana oil, Artemisia pallens, davanam, grown for its fragrant leaves and flowers, Asteraceae.
Deertongue oil, essential oil from the leaves of vanilla leaf, Liatris odoratissima, Asteraceae, contains coumarin.
Dill, (Anethum graveolens), contains carvone.
Diesel Tree oil, Copaifera langsdorffii.
Elecampane, (Inula helenium), Asteraceae
contains sesquiterpene lactones.
Elemi oil, Canarium luzonicum and Canarium ovatum, contains: | Phellandrene | Dipentene | Carvone | perfume oleoresins |.
Eucalyptus oil (Eucalyptus globulus), Myrtaceae.
Eucalyptus, Blue Gum, contains: | Cineole | Cymene | Pinene| Limonene | Phellandrene |.
Eucalyptus, Broad-leaved Peppermint | Piperitone | Phellandrene | | Camphene | Terpinenes | Thujune |.
Eucalyptus, Lemon-Scented Eucalyptus, contains | citronellal | citronellol | geranol | Pinene |.
Fennel, (Foeniculum vulgare), Apiaceae.
contains | anethole | Limonene | Phellandrene | Pinene | Camphene | Limonene | Fenchone occurs in some varieties |.
Fenugreek, (Trigonella foenum-graecum), Fabaceae.
Fir Needle oil, Silver Fir oil, contains: | Santene | Pinene | Limonene | Borneol | Bornyl acetate | Lauraldehyde |.
Frankincense oil, (Boswellia sacra), Bursuraceae
(oleo gum resin), contains monoterpene hydrocarbons | Pinene | dipentene | Limonene | thujene | phellandrine | octanol |.
Galangal, (Alpinia species), Zingiberaceae
contains | Pinene | Cineole |Eugenol | sesquiterpenes |.
Galbanum oil, contains | Pinene | edinol | cadinene | myrcene |.
Galip nut oil, (Canarium indicum), Burseraceae
Gardenia oil, contains benzyl acetate, phenyl acetate, linalool, terpineol.
Garlic, (Allium sativum var. sativum), Garlic oil, distilled oil of garlic, Amaryllidaceae.
Garlic, contains | allicin | allylpropyl disulfide | diallyl disulfide | citral | geraniol | linalool | Phellandrene |.
Geranium oil, contains | citronellol | geraniol | linalool | menthone | Phellandrene | Limonene |.
Ginger rhizome:Ginger oil, (Zingiber officinale), Zingiberaceae
contains | gingerin | gingenol | gingerone | zingiberine | linalool | Camphene | Phellandrene | citral | Cineole | Borneol |.
Ginkgo oil (Ginkgo biloba), Ginkgoaceae.
Ginseng oil, (Panax ginseng), Araliaceae
Golden rod oil, (Solidago canadensis), Asteraceae
Goldenseal oil, (Hydrastis canadensis), Ranunculaceae
Grapefruit oil, contains | Limonene | cadinene | neral | geraniol | fucocoumarins |.
Guaiacwood oil, contains guaiol, bulnesol, bulnesene, guaiene (in blood tests).
Helichrysum oil contains | nerol | neryl acetate | geraniol | Pinene | linalool | sesquiterpenes | furfurol |Eugenol |.
Henna tree oil, (Lawsonia inermis), Lythraceae
Hickory oil.
Hops oil, (Humulus lupulus), contains: | Humulene | Caryophellene | myrcene | farnesene |.
Horseradish oil, (Armoracia rusticana), Brassicaceae
contains isothiocyanate and phenylethyl isothiocyanate from bruised plant.
Hyacinth, contains | phenylethyl alcohol | Benzaldehyde | benzoic acid |.
Hyssop oil (Hyssopus officinalis), Lamiaceae.
contains | pinocamphone | Borneol | geranol | Limonene | Thujone | Myrcene | Caryophellene |.
Jasmine oil, (Jasmium officinale), Oleaceae
Java Oil contains geraniol, citronellal.
Juniper oil (Juniperus communis), Cupressaceae.
Jaborandi oil.
Juniper oil.
Cistus ladaniferus, Cistaceae.
contains | Pinene | Camphene | myrcene | Phellandrene | Limonene | Cineole | Borneol | geraniol.
Laurel oil, Laurus nobilis oil.
Lavender oil, True Lavender, (Lavendula angustifolia), Lamiaceae.
Lemonoil, citron lemon (Citrus x limon), Rutaceae.
contains | Limonene | terpinene | Pinene | linalool | geraniol |.
Lemon grass, (Cymbopogon citratus), Poaceae
contains citral, myrcene linalool, geraniol, nerol, farnesol.
Lime oil (Citrus x aurantifolia), Rutaceae.
Lime balm oil (Melissa officinalis), Lamiaceae.
Lovage oil (Levisticum officinale), Apiaceae.
Marigold oil (Calendula officinalis), Asteraceae.
Marjoram oil (Origanum marjorana).
Mint oil (Mentha arvensis), Lamiaceae.
Indian horseradish (Moringa oleifera), Moringaceae.
Mountain savory oil
Mountain tobacco oil, (Arnica montana), Asteraceae.
Mugwort oil, (Artemisia vulgaris), Asteraceae, contains | Thujone | Cineole | Pinene |.
Musk mallow oil, (Abelmoschus moschatus), Malvaceae.
Mustard oil, (Brassica) species, Brassicaceae.
Myrrh oil, (Commiphora myrrha), Burseraceae.
Myrrh (oleo gum resin), contains | heerabolene | Limonene | dipentene | Pinene |Eugenol | resins | gums |.
Myrtle (Myrtus communis), Myrtaceae.
Mint oil, Garden mint oil (Mentha sachalinensis), Lamiaceae.
Neem oil (Azadirachta indica), Meliaceae.
Neroli oil
Niaouli oil Melaleuca species, See: Melaleuca quinquenervia.
Nutmeg oil (Mystica fragrans), Lamiaceae.
Olive oil
Opopanax oil, Commiphora erytbraea, bisabol myrrh, Burseraceae. Sour orange oil, (Citrus x aurantium subsp. amara), Rutaceae
Sweet orange, "Orange", (Citrus x sinensis), Rutaceae
Oregano oil (Origanum vulgare), Lamiaceae.
Orris oil, (Iris florentina), Iridaceae
Palmarosa oil, (Cymbopogon martinii), Poaceae
Parsley oil (Petroselinium crispum), Apiaceae.
Patchouli oil (Pogostemon patchouli), Lamiaceae.
Peppermint oil (Mentha X piperita), Lamiaceae.
Perilla oil (Perilla frutescens), Lamiaceae.
Pennyroyal oil (Mentha pulegium), pennyroyal oil.
Pepper oil (Piper nigrum), Piperaceae, Black Pepper.
Peppermint oil.
Petitgrain oil.
Pimento oil.
Pine oil.
Pine, Dwarf Pine oil.
Pine, Longleaf Pine oil.
Pine, Scotch Pine oil.
Ravensara oil.
Red cedar oil.
Roman chamomile oil.
Rose buds (Rosa x centifolia), Rosaceae.
Rose, Cabbage Rose.
Rose, Damask Rose.
Rosehip oil, Rosa rubiginosa Rosemary, (Rosmarinus officinalis), Lamiaceae.
Rosewood oil.
Rue oil (Ruta graveolens), Rutaceae.
Sage oil (Salvia) species, Lamiaceae
Sandalwood oil, (Santalum album), Santalaceae
Santolina oil.
Sassafras tree oil (Sassafras albidum), Lauraceae.
Savine oil.
Savory oil, (Satureja species), Lamiaceae.
Schisandra oil.
Spanish broom seed oil (Genet absolute) (Spartium junceum), Fabaceae.
Spearmint oil.
Spikenard oil (Nardostachys jatamansi), Caprifoliaceae.
Spruceoil, (Picea species), Pinaceae
Star anise oil, (Illicium verum), Illiciaceae
Schinus Molle oil.
Snakeroot oil.
Spikenard oil.
Styrax oil, Levant Styrax oil.
Tagetes oil.
Tangerine oil.
Tarragon oil (Artemisia dracunculus), Asteraceae.
Tea tree oil.
Thyme oil (Thymus vulgaris), Lamiaceae.
Tsuga oil.
Turmeric oil, (Curcuma longa), Zingiberaceae.
Valerian oil, (Valeriana officinalis), Caprifoliaceae.
Vetiver grass oil, khus oil, (Chrysopogon zizanioides), Poaceae.
Tansy oil, (Tanacetum vulgare), Asteraceae.
Tarragon oil, (Artemisia dracunculus), Asteraceae, contains carvone terpenoid.
Tea tree oil: Thuja oil (Thuja occidentalis), Cupressaceae.
Tuberose oil Turmeric oil (Curcuma longa), Zingiberaceae.
Turpentine tree oil (Syncarpia glomulifera), Myrtaceae.
Valerian oil (Valeriana officinalis), Caprifoliaceae.
Vanilla oil (Vanilla planifolia), Orchidaceae.
Verbena oil (Verbena) species, Verbanaceae.
Vetiver grass oil (Chrysopogon zizanioides), Poaceae.
Violet oil (Viola odorata), Violaceae.
Wintergreen oil (Gaultheria procumbens), Ericaceae.
Wormseed oil (Dysphania ambrosioides), Amaranthaceae.
Wormwood oil (Artemisia absinthium), Asteraceae.
Yarrow oil (Achillea millefolium), Asteraceae.
Yew tree oil (Taxus baccata), Taxaceae.
Ylang ylang< oil/a> (Cananga odorata), Annonaceae.

16.6.2 Fixed oils.
Fixed oils (non-volatile oils, true oils, vegetable oils, aromatherapy carrier oils) are extracted from seeds or nuts by different methods.
They can be classed as "unrefined", "cold-pressed", "expeller-pressed", "refined", and extracted using solvents, heat and/or steam.
Fixed oils:
* make a permanent greasy mark on paper,
* cannot be distilled unchanged,
* do not evaporate at room temperature, so are called "carrier oils", but do not volatilize on heating without decomposition,
* are glycerides of fatty acids,
* harden on exposure to the air.
Fixed oils, base oils, carrier oils are oily, non-volatile, usually from the seed or nut.
They are called "fixed oils", because they have large molecules so do not evaporate like essential oils.
Carrier oils are mixtures of unsaturated and saturated fatty acids with some traces of vitamins, minerals and other trace plant constituents.

16.6.2a List of fixed oils.
Aguaje oil (Buriti oil), Almond butter, Almond oil sweet.
Andiroba oil, Apricot kernel oil, Arachis oil (peanut oil), Argane oil, Avocado butter, Avocado oil.
Babassu nut oil, Baobab oil, Bayberry oil (Laurel seed oil).
Beeswax, Ben oil (Moringa oil), Bilberry seed oil, Blackcurrant seed oil.
Bois de rose oil, rosewood oil (Aniba rosaeodora), Lauraceae, Borage oil, Brazil nut oil.
Calendula oil, Calophyllum inophylum oil (Tamanu nut oil), Camelina sativa oil, Camellia oil.
Candlenut oil (Aleurites moluccana), Canola oil (Brassica napus) 16.14.5
Cape Chestnut oil, Capuacu butter, Caraway black oil, Carrot oil, Cashew kernel oil.
Castor oil, chaulmoogra seed oil, Cherry kernel oil, Chia oil, Cocoa butter, Cocoa oil organic, Coconut oil.
Cod liver oil
Coffee oil
Corn oil corn oil (Zea mays)
Cotton seed oil, cottonseed oil.
Crabwood oil (Andiroba seed)
Cranberry seed oil, Cumin black oil.
Dhupa butter
Echium seed oil
Emu oil from the emu bird
Evening primrose oil
Flax seed oil (Linseed oil).
Gold of pleasure oil (Camelina sativa)
Grape seed oil, Groundnut oil (Peanut oil).
Hazelnut oil, Hempseed oil, Illipe butter, Jojoba oil, Kalahari oil, Karanja oil, Kemiri oil (Kukui nut oil).
Kiwifruit oil, Kokum butter (Garcinia indica), Krabwood oil, (Andiroba oil), Kukui nut oil, Lard (pig fat).
Laurel seed oil, Lettuce seed oil, Lingonberry oil, Linseed oil.
Macadamia nut oil, Macadamia (Macadamia integrifolia), Proteaceae.
Mango kernel butter, Mango seed oil, Manketti nut oil.
Margosa oil, Marigold oil (Calendula oil), Marula oil, Meadow foam seed oil, Mobola plum oil, Mongongo seed oil.
Moringa oil, Mowrah butter, Mustard oil (Brassica campestris).
Neem tree, (Azadirachta indica), Meliaceae
Meliaceae, Ngali nut oil.
Olives, Olea europaea, olive oil: 19.2.0
Ootanga oil (Watermelon oil), Orchid oil.
Palm kernel oil (from kernel of oil palm, Elaeis guineensis).
Palm oil (from mesocarp of oil palm, Elaeis guineensis).
Papaya seed oil, Parinari oil, Passionflower oil, Peach kernel oil, Peanut oil, Pecan nut oil, Perilla oil.
Phulwara butter, Pistachio nut oil, Plum kernel oil, Pomegranate oil, Poppy seed oil, Pumpkin seed oil.
Rapeseed oil (Canola oil), Raspberry seed oil, Rice bran oil, Rocket seed oil, Rosehip seed oil.
Safflower seed oil (Carthamus tinctorius), Sal butter, Salmon oil, Sea buck thorn oil, Seaside plum oil (Ximenia oil).
Sesame seed oil, Sesame oil (Sesamum indicum), Shark liver oil, Shea oil, Shea butter, Soya bean oil, soybean oil (Glycine max).
Squalene oil (vegetable oil), St John's Wort oil, Strawberry seed oil, Sunflower oil (Helianthus annuus), Sunflower seed oil.
Tamanu nut oil, Tucuma butter, Tung oil (Aleurites fordii), Urucum oil, Walnut oil, Watermelon seed oil.
Wheat germ oil (cold pressed and refined), Ximenia oil (Seaside plum oil), Yangu oil (Cape Chestnut oil).

16.6.3 Vegetable oils.
Vegetable oils, plant oils, are triglycerides extracted from plants by pressure or maceration that are usually liquid at room temperature.
Vegetable oils include cooking oils, e.g. canola oil, solid oils, e.g. cocoa butter, oils in paint, e.g. linseed oil, and industrial oils.
Pressed vegetable oils are extracted from the plants, usually seed, using a screw press or a ram press, which forces oil out, leaving seed cake.
Note that castor oil, linseed oil and tung oil are not edible.

16.6.3a List of vegetable oils.
Aniline oil, oily, poisonous, liquid amine, is used to make dyes, plastics, medicines.
Castor oil
Clove oil
Coconut oil
Eucalyptus oil
Evening primrose, (Oenothera biennis), Onagraceae
Lavender oil
Lemon oil
Linseed oil
Neatsfoot oil
Oil of wintergreen, methyl salicylate
Pear oil, Prepare amyl acetate
Pennyroyal
Salad oil
Tea tree oil
Tung oil
Vanilla oil
Experiment
Prepare soap with vegetable oils: 12.12.2