Ketoisanic acid

Ketoisanic acid
Names
	IUPAC name 8-oxooctadec-17-en-9,11-diynoic acid
	Other names 8-O=18:3Δ9a,11a,17
Identifiers
CAS Number	64144-74-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:197078;
ChemSpider	57514446;
PubChem CID	71380416;
CompTox Dashboard (EPA)	DTXSID10802931;
	InChI InChI=1S/C18H24O3/c1-2-3-4-5-6-7-8-11-14-17(19)15-12-9-10-13-16-18(20)21/h2H,1,3-6,9-10,12-13,15-16H2,(H,20,21) Key: SSLASXCMMXZERF-UHFFFAOYSA-N;
	SMILES C=CCCCCC#CC#CC(=O)CCCCCCC(=O)O;
Properties
Chemical formula	C18H24O3
Molar mass	288.387 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Ketoisanic acid is a linear fatty acid composed of 18 carbon atoms, with two triple bonds in the positions 9≡10 and 11≡12, a double bond in the position 17=18, and a ketone substituent in the position 8. This is one of the rare polyacetylenic acids with conjugated triple bonds, the oxygenated isanic acid.^[1]

Natural occurrence

The acid can be detected, at concentrations of 1–3%, together with isanic and isanolic acid, in the seed oil of the tree Ongokea gore or Ongokea klaineana; both are plants from equatorial Africa, called "isano" in the local language.^[2]^[3]^[4]

References

^ "LIPID MAPS". lipidmaps.org. Retrieved 25 April 2025.
^ Miller, Roger W.; Weisleder, David; Plattner, Ronald D.; Smith Jr., C. R. (1977). "cis-Enediyne chromophore of isano oil". Lipids. 12 (8): 669–675. doi:10.1007/BF02533763. ISSN 1558-9307. Retrieved 25 April 2025.
^ Miller, Roger W.; Weisleder, David; Kleiman, Robert; Plattner, Ronald D.; Smith, Cecil R. (1 January 1977). "Oxygenated fatty acids of isano oil". Phytochemistry. 16 (7): 947–951. Bibcode:1977PChem..16..947M. doi:10.1016/S0031-9422(00)86701-1. ISSN 0031-9422. Retrieved 25 April 2025.
^ Badami, R. C.; Patil, K. B. (1 January 1980). "Structure and occurrence of unusual fatty acids in minor seed oils". Progress in Lipid Research. 19 (3): 119–153. doi:10.1016/0163-7827(80)90002-8. ISSN 0163-7827. Retrieved 25 April 2025.

[1] "LIPID MAPS". lipidmaps.org. Retrieved 25 April 2025.

[2] Miller, Roger W.; Weisleder, David; Plattner, Ronald D.; Smith Jr., C. R. (1977). "cis-Enediyne chromophore of isano oil". Lipids. 12 (8): 669–675. doi:10.1007/BF02533763. ISSN 1558-9307. Retrieved 25 April 2025.

[3] Miller, Roger W.; Weisleder, David; Kleiman, Robert; Plattner, Ronald D.; Smith, Cecil R. (1 January 1977). "Oxygenated fatty acids of isano oil". Phytochemistry. 16 (7): 947–951. Bibcode:1977PChem..16..947M. doi:10.1016/S0031-9422(00)86701-1. ISSN 0031-9422. Retrieved 25 April 2025.

[4] Badami, R. C.; Patil, K. B. (1 January 1980). "Structure and occurrence of unusual fatty acids in minor seed oils". Progress in Lipid Research. 19 (3): 119–153. doi:10.1016/0163-7827(80)90002-8. ISSN 0163-7827. Retrieved 25 April 2025.

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