Heptanoic acid

Heptanoic acid

Names
IUPAC name Heptanoic acid
Other names Enanthic acid; Oenanthic acid; n-Heptylic acid; n-Heptoic acid
Identifiers
CAS Number	111-14-8 Y
ChEBI	CHEBI:45571 Y
ChEMBL	ChEMBL320358 Y
ChemSpider	7803 Y
DrugBank	DB02938 Y
Jmol 3D model	Interactive image
KEGG	C17714 Y
PubChem	8094
UNII	THE3YNP39D Y
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
SMILES O=C(O)CCCCCC
Properties
Chemical formula	C7H14O2
Molar mass	130.19 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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. 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 pyrolyzed 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.

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.