FComEx: Azelaic acid (PC000105)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:24 UTC

Update date

2017-01-19 02:36:12 UTC

FoodComEx ID

PC000105

FoodDB Record

FDB012192

Chemical Information

Name

Azelaic acid

Description

Azelaic acid, also known as 1,9-nonanedioate, AZA or azelex, is a saturated nine-carbon dicarboxylic acid. It ocurrs in all living organisms, ranging from bacteria to humans. AZA possesses a variety of in vitro and in vivo biological activities. In aerobic bacteria, azelaic acid reversibly inhibits several oxidoreductive enzymes including tyrosinase, mitochondrial enzymes of the respiratory chain, thioredoxin reductase, 5-alpha-reductase, and DNA polymerases. It is currently used as a topical treatment of mild to moderate inflammatory acne vulgaris, due to its antibiotic effects on skin bacteria. Its effectiveness is similar to that of other agents without the systemic side effects of oral antibiotics or the allergic sensitization of topical benzoyl peroxide and with less irritation than tretinoin. Azelaic acid is less expensive than certain other prescription acne preparations, but it is much more expensive than nonprescription benzoyl peroxide preparations. Whether it is safe and effective when used in combination with other agents is not known. (PMID: 7737781, 8961845). In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection. It serves as a signal that induces the accumulation of salicylic acid, an important component of the plants defensive response (PMID: 19342588). AZA is found in high abundance in several crop plants including wheat, rye, and barley. Azelaic acid has been detected, but not quantified in, a few different foods, such as asparagus, common beans, and potato. This could make azelaic acid a potential biomarker for the consumption of these foods. Azelaic acid is a precursor to a number of industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners.

CAS Number

123-99-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1, 9-Nonanedioic acid	biospider
1,7-Dicarboxyheptane	biospider
1,7-Heptanedicarboxylate	biospider
1,7-Heptanedicarboxylic acid	db_source
1,9-Nonanedioate	biospider
1,9-Nonanedioic acid	biospider
1tuf	biospider
Acide azelaique	ChEBI
Acido azelaico	biospider
Acidum azelaicum	biospider
Anchoate	biospider
Anchoic acid	db_source
Azalaic acid	biospider
Azelaate	Generator
Azelaic acid	biospider
Azelaic acid (usan/inn)	biospider
Azelaic acid [usan:inn]	biospider
Azelaic acid polyanhydride	biospider
AZELAIC ACID, 95%	biospider
Azelaic acid, INN, USAN	db_source
Azelaic polyanhydride	biospider
Azelaicacidtech	biospider
Azelainic acid	biospider
Azelainsaeure	ChEBI
Azelate	biospider
Azelex	biospider
Azelex (TN)	biospider
Azleaic acid	biospider
Emerox 1110	biospider
Emerox 1144	db_source
Emery's L-110	biospider
Finacea	biospider
Finacea (TN)	biospider
Finevin	biospider
Heptanedicarboxylic acid	biospider
Lepargylate	biospider
Lepargylic acid	db_source
N-nonanedioate	biospider
N-nonanedioic acid	biospider
Nonandisaeure	ChEBI
Nonanedioate	biospider
Nonanedioic acid	ChEBI
Nonanedioic acid azelaic acid	biospider
Nonanedioic acid homopolymer	biospider
Nonanedioic acid, homopolymer	biospider
Poly(azelaic anhydride)	biospider
Polyazelaic anhydride	biospider
Skinorem	biospider
Skinoren	db_source
ZK 62498	db_source

Chemical Formula

C9H16O4

IUPAC name

nonanedioic acid

InChI Identifier

InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)

InChI Key

BDJRBEYXGGNYIS-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CCCCCCCC(O)=O

Average Molecular Weight

188.2209

Monoisotopic Molecular Weight

188.104859

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents