CHEM 30B Dr. R. Rinehart

 Alcohols, Phenols, Ethers, Thiols, …

THIOLS and related compounds

Common Name

“IUPAC” Name

Condensed Structure

Line Structure

Comments

methyl mercaptan

methanethiol

CH₃SH

added to natural gas as a warning odorant

isopentyl mercaptan

3-methyl-1-butanethiol

(CH₃)₂CHCH₂CH₂SH

the major component of “skunk essence”

BAL [British Anti-Lewisite] or dimercaprol

2,3-dimercapto-1-propanol

HSCH₂CHSHCH₂OH

antidote to Lewisite, an arsenic-containing poison gas that has been used as a chemical  warfare agent

cysteine

2-amino-3-thiopropanoic acid

HSCH₂CHNH₂CO₂H

one of the 20 common amino acids -- the -SH group is frequently part of the active site of enzymes

lipoic acid

thioctic acid

xxx

below

oxidized and reduced forms of an important coenzyme

dihydrolipoic acid

6,8-dithiooctanoic acid

HS(CH₂)₂CHSH(CH₂)₄CO₂H

below

coenzyme A

xxx

xxx

below

a critical coenzyme in the metabolism of carbohydrates, fats, and proteins

a-lipoic acid [thioctic acid]

dihydrolipoic acid

CoenzymeA