FComEx: Heptadecanoic acid (PC000845)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:03 UTC

Update date

2017-01-19 02:36:38 UTC

FoodComEx ID

PC000845

FoodDB Record

FDB004676

Chemical Information

Name

Heptadecanoic acid

Description

Heptadecanoic acid, also known as margaric acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Heptadecanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heptadecanoic acid is a constituent of Erythrina crista-galli trunkwood and bark. Heptadecanoic acid is a fatty acid of exogenous (primarily ruminant) origin. Many "odd" lengths long chain amino acids are derived from the consumption of dairy fats (milk and meat). Heptadecanoic acid is usually found in trace amounts and constitutes 0.61% of milk fat and 0.83% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products (PMID: 9701185). It is a common constituent of lipids, such as those present in Physalia physalis (Portuguese-man-of-war). Heptadecanoic acid has pheromonic and allomonic properties for insects and reptiles. The subcaudal gland secretions of the European badger (Meles meles) and the occipital gland secretions of male bactrian camels (Camelus bactrianus) contain many pheromonic chemicals, including heptadecanoic acid, that aid in finding and selection of mates (PMID: 24414593). Heptadecanoic acid is an attractant of the khapra beetle (Trogoderma granarium) and the yellow fever mosquito (Aedes aegypti) but as a repellent of the common house mosquito (Culex pipiens; doi: 10.5962/bhl.title.49749). Heptadecanoic acid is also found in the precloacal gland secretions of many reptiles belonging to the order squamata, including the common leopard gecko (Eublepharis macularius; PMID 24264893) and the European viper (Vipera berus), where it is used for the identification of sexual partners (doi:10.1007/bf00579807).

CAS Number

506-12-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
17:0	manual
CH3-[CH2]15-COOH	ChEBI
Daturic acid	biospider
Daturinic acid	db_source
Heptadecanoate	biospider
Heptadecoate	Generator
Heptadecoic acid	biospider
Heptadecylate	Generator
Heptadecylic acid	biospider
Margarate	biospider
Margaric acid	db_source
Margarinate	biospider
Margarinic acid	biospider
Margarinsaeure	ChEBI
Margaroate	HMDB
Margaroic acid	HMDB
N-Heptadecanoate	biospider
N-Heptadecanoic acid	biospider
N-Heptadecoate	biospider
N-Heptadecoic acid	biospider
N-Heptadecylate	biospider
N-Heptadecylic acid	biospider
Normal-heptadecanoate	HMDB
Normal-heptadecanoic acid	HMDB

Chemical Formula

C17H34O2

IUPAC name

heptadecanoic acid

InChI Identifier

InChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)

InChI Key

KEMQGTRYUADPNZ-UHFFFAOYSA-N

Isomeric SMILES

CCCCCCCCCCCCCCCCC(O)=O

Average Molecular Weight

270.4507

Monoisotopic Molecular Weight

270.255880332

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents