Hypogeic acid

Hypogeic acid

Names
IUPAC name (E)-hexadec-7-enoic acid
Other names Hypoglycemic acid, trans-7-hexadecenoic
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	4895966
PubChem CID	6365142
CompTox Dashboard (EPA)	DTXSID301009353
InChI InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h9-10H,2-8,11-15H2,1H3,(H,17,18)/b10-9+ Key: PJHOFUXBXJNUAC-MDZDMXLPSA-N
SMILES CCCCCCCC/C=C/CCCCCC(=O)O
Properties
Chemical formula	C16H30O2
Molar mass	254.414 g·mol−1
Appearance	colorless needles
Melting point	33 °C (91 °F; 306 K)
Boiling point	374.80 °C (706.64 °F; 647.95 K) [1]
Solubility in water	soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Hypogeic acid is a monounsaturated fatty acid of the Omega-9 group. Its chemical formula is C₁₆H₃₀O₂, and its delta notation is 16:1Δ7t. The acid is composed of 16 carbon atoms, with one double bond in position 7=8 in trans-configuration. The compound has the structural formula CH₃-(CH₂)₇-CH=CH-(CH₂)₅-COOH.

Hypogeic acid is found in Monascus purpureus and Arachis hypogaea . The compound can also be isolated from autotrophic bacterial cultures associated with the accumulation of sulfate in biofilters. ^[2]

Discovery

The acid was initially found by Gössmann and Scheven in 1854–1855, together with palmitic and arachidic acid in earth-nut oil that was used as a substitute for olive oil. ^[3]

Physical properties

Hypogeic acid is soluble in alcohol and forms colorless needle-like crystals. ^[3]

References

1. "metabocard for Hypogeic acid (HMDB0002186)". hmdb.ca. Retrieved 2 April 2025.
2. "Hypogeic acid | Mono-unsaturated Fatty Acids | MedChemExpress". MedchemExpress.com. Retrieved 2 April 2025.
3. Roscoe, Henry Enfield (1890). A Treatise on Chemistry: The chemistry of the hydrocarbons and their derivatives, or Organic chemistry. D. Appleton and Company. p. 419. Retrieved 2 April 2025.