Enanthic Acid - Wikipedia

Enanthic acid[1]

Names
Preferred IUPAC name Heptanoic acid
Other names Enthanoic acid; Enthanylic acid; Heptoic acid; Heptylic acid; Oenanthic acid; Oenanthylic acid; 1-Hexanecarboxylic acid; C7:0 (lipid numbers)
Identifiers
CAS Number	111-14-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:45571 Y
ChEMBL	ChEMBL320358 Y
ChemSpider	7803 Y
DrugBank	DB02938 Y
ECHA InfoCard	100.003.490
KEGG	C17714 Y
PubChem CID	8094
UNII	THE3YNP39D Y
CompTox Dashboard (EPA)	DTXSID2021600
InChI InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9) YKey: 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	130.187 g·mol−1
Appearance	colorless 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)
Magnetic susceptibility (χ)	−88.60·10−6 cm3/mol
Hazards
GHS labelling:
Pictograms	[2]
Signal word	Danger[2]
Hazard statements	H314[2]
Precautionary statements	P261, P271, P280, P303+P361+P353, P304+P340+P310, P305+P351+P338[3]
NFPA 704 (fire diamond)	3 2 0
Lethal dose or concentration (LD, LC):
LD50 (median dose)	6400 mg/kg (oral, rat)
Related compounds
Related compounds	Hexanoic acid, Octanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Chemical compound

Enanthic acid, also called heptanoic acid, is an organic compound composed of a seven-carbon chain terminating in a carboxylic acid functional group. It is a colorless 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. Salts and esters of enanthic acid are called enanthates or heptanoates.

Its name derives from the Latin oenanthe which is in turn derived from the Ancient Greek oinos "wine" and anthos "blossom."

Production

[edit]

The methyl ester of ricinoleic acid, obtained from castor bean oil, is the main commercial precursor to enanthic acid. It is pyrolyzed to the methyl ester of 10-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.[4]

Laboratory preparations of enanthic acid include permanganate oxidation of heptanal[5] and 1-octene.[6]

Uses

[edit]

Enanthic acid is used in the preparation of esters, such as ethyl enanthate, which are used as artificial flavors. Enanthic acid is used to esterify anabolic steroids in the preparation of drugs such as testosterone enanthate, trenbolone enanthate, drostanolone enanthate, and methenolone enanthate.

The triglyceride of enanthic acid is known as triheptanoin, which is a medical food.

Safety

[edit]

Enanthic acid is corrosive.[2]

See also

[edit]

• List of saturated fatty acids
• List of carboxylic acids

References

[edit]

1. ^ a b Merck Index, 11th Edition, 4581
2. ^ a b c d "Heptanoic Acid - Pubchem".
3. ^ "Heptanoic acid". Sigma-Aldrich. Retrieved 2025-03-29.
4. ^ David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2
5. ^ John R. Ruhoff (1936). "N-Heptanoic Acid". Organic Syntheses. 16: 39. doi:10.15227/orgsyn.016.0039.
6. ^ Donald G. Lee, Shannon E. Lamb, Victor S. Chang (1981). "Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid". Organic Syntheses. 60: 11. doi:10.15227/orgsyn.060.0011.{{cite journal}}: CS1 maint: multiple names: authors list (link)

v t e Lipids: fatty acids
Saturated	Acetic (C2) Propionic (C3) Butyric (C4) Valeric (C5) Caproic (C6) Enanthic (C7) Caprylic (C8) Pelargonic (C9) Capric (C10) Undecylic (C11) Lauric (C12) Tridecylic (C13) Myristic (C14) Pentadecylic (C15) Palmitic (C16) Margaric (C17) Stearic (C18) Nonadecylic (C19) Arachidic (C20) Heneicosylic (C21) Behenic (C22) Tricosylic (C23) Lignoceric (C24) Pentacosylic (C25) Cerotic (C26) Carboceric (C27) Montanic (C28) Nonacosylic (C29) Melissic (C30) Hentriacontylic (C31) Lacceroic (C32) Psyllic (C33) Geddic (C34) Ceroplastic (C35) Hexatriacontylic (C36) Heptatriacontanoic (C37) Octatriacontanoic (C38) Nonatriacontanoic (C39) Tetracontanoic (C40)
ω−3 Unsaturated	Octenoic (8:1) Decenoic (10:1) Decadienoic (10:2) Lauroleic (12:1) Laurolinoleic (12:2) Myristovaccenic (14:1) Myristolinoleic (14:2) Myristolinolenic (14:3) Palmitolinolenic (16:3) Palmitidonic (16:4) α-Linolenic (18:3) Stearidonic (18:4) α-Parinaric (18:4) Dihomo-α-linolenic (20:3) Eicosatetraenoic (20:4) Eicosapentaenoic (20:5) Clupanodonic (22:5) Docosahexaenoic (22:6) 9,12,15,18,21-Tetracosapentaenoic (24:5) 6,9,12,15,18,21-Tetracosahexaenoic (24:6)
ω−5 Unsaturated	Myristoleic (14:1) Palmitovaccenic (16:1) α-Eleostearic (18:3) β-Eleostearic (trans-18:3) Punicic (18:3) 7,10,13-Octadecatrienoic (18:3) 9,12,15-Eicosatrienoic (20:3) β-Eicosatetraenoic (20:4)
ω−6 Unsaturated	Obtusilic acid (10:1) 8-Tetradecenoic (14:1) 12-Octadecenoic (18:1) Linoleic (18:2) Linolelaidic (trans-18:2) γ-Linolenic (18:3) Calendic (18:3) Pinolenic (18:3) Dihomo-linoleic (20:2) Dihomo-γ-linolenic (20:3) Sciadonic (20:3) Arachidonic (20:4) Adrenic (22:4) Osbond (22:5)
ω−7 Unsaturated	Palmitoleic (16:1) Vaccenic (18:1) Rumenic (18:2) Paullinic (20:1) 7,10,13-Eicosatrienoic (20:3)
ω−9 Unsaturated	Hypogeic (16:1) Oleic (18:1) Elaidic (trans-18:1) Gondoic (20:1) Erucic (22:1) Nervonic (24:1) 8,11-Eicosadienoic (20:2) Mead (20:3) Ximenic (26:1)
ω−10 Unsaturated	Sapienic (16:1)
ω−11 Unsaturated	Gadoleic (20:1) Cetoleic (22:1) Lumequeic (30:1)
ω−12 Unsaturated	4-Hexadecenoic (16:1) Petroselinic (18:1) 8-Eicosenoic (20:1)