CHEM 30B Dr. R. Rinehart  

 Alcohols, Phenols, Ethers, Thiols, …

PHENOLS

Common Name

“IUPAC” Name

Condensed Structure

Line Structure

Comments

phenol

phenol

C₆H₅OH

Lister’s original disinfectant (carbolic acid in 1:10,000 dilution); used in embalming and by podiatrists to destroy nail bed on ingrown nails. Dangerous – penetrates skin, causing burns that take weeks to heal – and you feel nothing because it has destoyed the nerve endings!

ortho-cresol

2-methylphenol

o-CH₃C₆H₄OH

found in creosote, a wood preservative

meta-cresol

3-methylphenol

m-CH₃C₆H₄OH

found in creosote, a wood preservative

para-cresol

4-methylphenol

p-CH₃C₆H₄OH

found in creosote, a wood preservative

catechol

1,2-benzenediol

o-C₆H₄(OH)₂

the catechol group is found in dopamine and norepinephrine

resorcinol

1,3-benzenediol

m-C₆H₄(OH)₂

found in some topical medications for acne

hydroquinone

1,4-benzenediol

p-C₆H₄(OH)₂

a free-radical scavenger; used in skin  bleaching 

eugenol

2-methoxy-4-

(2-propenyl)phenol

xxx

main component of oil of cloves; antibacterial and dental analgesic

thymol

5-methyl-2-isopropyl phenol

xxx

topical antiseptic; used in cough drops; active against worm infestation

BHA

butylated hydroxyanisole

2-tert-butyl-4-

methoxyphenol

xxx

 used as an antioxidant in food packaging (check your cereal)

BHT

2,6-di-tert-butyl-4-

methylphenol

xxx

used as an antioxidant in food packaging (check your cereal)

ortho-phenylphenol

2-phenylphenol

o-C₆H₅C₆H₄OH

the active ingredient in Lysol spray

pentachlorophenol

pentachlorophenol

C₆Cl₅OH

used as wood preservative

hexachlorophene

don’t ask!

xxx

used in germicidal soaps

[now requires Rx]

tyrosine

2-amino-3-(4-hydroxy

phenyl)-

propanoic acid

p-HOC₆H₄CH₂CHNH₂CO₂H

one of the 20 common amino acids

tetrahydrocannabinol

xxx

xxx

below

psychoactive principle of marijuana

vitamin E

alpha-tocopherol

xxx

below

a fat-soluble antioxidant

D⁹-tetrahydrocannabinol [THC]

a-tocopherol [vitamin E]