Unit 5.3: Phenols to Other Ester Volatile Oils

Shikimate pathway

Which pathway do phenol volatile oils come from?

clove

Eugenia caryophyllus

false

*new

True or False:

Syzygium aromaticum is the old scientific name of clove

Myrtaceae

clove/Eugenia caryophyllus family?

clove

Consituent: Eugenol (4-allyl-2-methoxyphenol)

clove

• Antiseptic in toothache drops

• Stimulant aromatic, potential anticarcinogenic

clove

• Oil of clove can also be used for synthesis of vanillin

thyme

Thymus vulgaris, T. zygis

Lamiaceae

thyme/Thymus vulgaris, T. zygis family?

40% thymol and carvacrol

responsible for antiseptic, antitussive and expectorant properties of thyme

Flavones

may be responsible for spasmolytic effect of the leaves of thyme

Biphenyls

for deodorant properties of thyme

Wild thyme

Thymus serpyllum

Wild thyme (Thymus serpyllum)

less powerful in actions

• Traditionally used for respiratory infections, GI problems, and skin conditions requiring an antiseptic

Oregano (pot marjoram)

Origanum onites

Oregano (wild marjoram)

Origanum vulgare

Lamiaceae

oregano family?

Oregano

Constituents: Carvacrol, thymol

oregano

• Have thyme-like odor

• Strong antiseptic properties

• Traditionally used for digestive disorders, pharyngeal infections and mild fevers

cade tar

Juniperus oxycedrus

Cupressaceae

cade tar/Juniperus oxycedrus family?

cade tar

Constituents: Cadinene

cade tar

Antieczematic

juniper tar

Pinus palustris

Pinaceae

juniper tar/Pinus palustris family?

juniper tar

Constituents: Phenol, creosol, naphthalene

juniper tar

Antieczematic, anti-psoriasis

myricia oil/bay oil

Pimenta racemosa

Myrtaceae

myricia oil/bay oil/Pimenta racemosa family?

myricia oil/bay oil

Constituents: Eugenol

myricia oil/bay oil

Diaphoretic

creosote

Fagus grandiflora

Fagaceae

creosote/Fagus grandiflora family?

creosote

Constituents: Guaiacol, creosol

creosote

Disinfectant

PHENOLIC ETHERS

Similar to phenol volatile oils, but with an ether moiety (usually methoxy groups)

Phenols

Which classification:

Examples: Anethole, safrole, asarone

Phenolic ethers

Which classification:

Ex. Carvacrol, thymol, eugenol

FENNEL

Finocchio

Apiaceae

FENNEL/Foeniculum vulgare family

FENNEL

Foeniculum vulgare

FENNEL

Constituents: Fenchone, trans-anethole (55-75%), anisaldehyde, estragole

• Nmt 7.5% fenchone

FENNEL

Purgative

false

*seeds are slender and have no curve

True or False:

fennels have a smilar appearance to anise except its seeds are slender and have a curve

ANISE

Aniseed

ANISE

Pimpinella anisum

Apiaceae

ANISE/Pimpinella anisum family?

ANISE

Constituents: Anethole, chavicol, methylchavicol • Limit of 0.1% for fenchone and 0.01% foeniculin

ANISE

For cough and cold

NUTMEG

Myristica fragrans

Myristicaceae

NUTMEG/Myristica fragrans family?

Nutmeg liver

Constituents: Primarily a-pinene, b-pinene, sabinene, myristicin

NUTMEG

Flavoring agent and carminative

Myristicin and elemicin

components of nutmeg that are hallucinogenic, convulsive at high doses

STAR ANISE

Badiam, Chinese star anise

STAR ANISE; (Japanese)

Illicium verum, I. anisatum (___________)

Illiciaceae

STAR ANISE/Illicium verum, I. anisatum family?

STAR ANISE

Constituents: 86% trans-anethole

Japanese star anise

poisons sikimin and sikimitoxin

STAR ANISE

Flavoring agents and carminatives

shikimic acid; oseltamivir

Though star anise is poisonous, the ________ _____ may be used as starting material for synthesis of the antidrug drug ________

SWEET FLAG

Acorus calamus

Acoraceae

Constituents: Asarone, related to myristicin

Acoraceae

SWEET FLAG/Acorus calamus family?

SWEET FLAG

• Germination inhibitors of lettuce seeds • Has AChE inhibitory activity

SASSAFRAS

Sassafras albidum

Lauraceae

SASSAFRAS/Sassafras albidum family?

SASSAFRAS

Constituents: Safrole

true

True or False:

Safrole is toxic

SASSAFRAS

Flavoring agent (previously in rootbeer)

OXIDES/ PEROXIDES

Often seen as cyclic ethers

OXIDES/ PEROXIDES

Which classification?

Examples: Eucalyptol, ascaridole

EUCALYPTUS

Blue-gum

EUCALYPTUS

Eucalyptus globulus

Myrtaceae

EUCALYPTUS/Eucalyptus globulus family?

EUCALYPTUS

Constituents: Cineole (70%)

Cineole

aka eucalyptol or cajuputol

EUCALYPTUS

• Alleviates symptoms of nasopharyngeal infections

• For treating coughs and as decongestant

• Ointment and liniments

Eucalyptus deglupta

Mindanao gum

Mindanao gum

Stimulant, antiseptic, antimalarial

TEA-TREE

Melaleuca alternifolia

Myrtaceae

TEA-TREE/Melaleuca alternifolia family?

TEA-TREE

Antiseptic creams for skin treatment, inhalations, and pastilles for throat infections

WORMSEED/ ALPASOTES

Chenopodium ambrosioides

Chenopodiaceae

WORMSEED/ALPASOTES/Chenopodium ambrosioides family?

WORMSEED/ ALPASOTES

Constituents: Asacaridole

WORMSEED/ ALPASOTES

Antheminthic

ESTERS

Constitutes a massive array of odorous principles from fruits, plants, and food

LAVENDER

Lavendula spp.

Lamiaceae

LAVENDER/Lavendula spp. family?

L. officinalis

True lavender

best oil in high altitude

Lavande Moyenne

less esteemed

Low altitude

LAVENDER

Constituents: Linalool, linalyl acetate are primary constituents

hybried species

which species of lavender has 6-9% esters

Oil of spike

which component of lavender has little ester content but high proportion of free alcohols - cheap perfumery

lavender

Camphor should not exceed 1%

flower

which part of lavender is used for flatulence, colic, and depressive headache

oil

which part of lavender is used to mask disagreeable odor, flatulence and rheumatic pain, as well as aromatherapy

WINTERGREEN

Teaberry, checkerberry

WINTERGREEN

Gaultheria procumbens