Heptanoic acid

Heptanoic acid[1]
IUPAC name Heptanoic acid
Other names Enanthic acid; Oenanthic acid; n-Heptylic acid; n-Heptoic acid
Identifiers
CAS number	111-14-8 Y
PubChem	8094
ChemSpider	7803 Y
UNII	THE3YNP39D Y
DrugBank	DB02938
KEGG	C17714 Y
ChEBI	CHEBI:45571 Y
ChEMBL	CHEMBL320358 Y
Jmol-3D images	Image 1
SMILES O=C(O)CCCCCC
InChI InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9) Y Key: MNWFXJYAOYHMED-UHFFFAOYSA-N Y InChI=1/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9) Key: MNWFXJYAOYHMED-UHFFFAOYAP
Properties
Molecular formula	C7H14O2
Molar mass	130.18 g mol−1
Appearance	Oily liquid
Density	0.9181 g/cm3 (20 °C)
Melting point	−7.5 °C; 18.5 °F; 265.6 K
Boiling point	223 °C; 433 °F; 496 K
Solubility in water	0.2419 g/100 mL (15 °C)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Heptanoic acid, also called enanthic acid, is an organic compound composed of a seven-carbon chain terminating in a carboxylic acid. It is an oily liquid with an unpleasant, rancid odor.^[1] It contributes to the odor of some rancid oils. It is slightly soluble in water, but very soluble in ethanol and ether.

Production and uses

The methyl ester of ricinoleic acid, obtained from castor bean oil is the main commercial precursor to heptanoic acid. It is hydrolyzed to the methyl ester of undecenoic acid and heptanal, which is then air oxidized to the carboxylic acid. Approximately 20,000 tons were consumed in Europe and US in 1980.^[2]

Ricinoleic acid is the main precursor to heptanoic acid.

Heptanoic acid is used in the preparation of esters, such as ethyl heptanoate, which are used in fragrances and as artificial flavors.

Heptanoic acid is used to esterify steroids in the preparation of drugs such as testosterone enanthate, trenbolone enanthate, drostanolone enanthate and methenolone enanthate (Primobolan). It is also one of many additives in cigarettes.

References