Chemistry:Ketoisanic acid

From HandWiki
Ketoisanic acid
Names
IUPAC name
8-oxooctadec-17-en-9,11-diynoic acid
Other names
8-O=18:3Δ9a,11a,17
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
Properties
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
Tracking categories (test):

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

  1. "LIPID MAPS". lipidmaps.org. https://www.lipidmaps.org/databases/lmsd/LMFA01060211. 
  2. Miller, Roger W.; Weisleder, David; Plattner, Ronald D.; Smith Jr., C. R. (1977). "cis-Enediyne chromophore of isano oil" (in en). Lipids 12 (8): 669–675. doi:10.1007/BF02533763. ISSN 1558-9307. https://aocs.onlinelibrary.wiley.com/doi/10.1007/BF02533763. 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. doi:10.1016/S0031-9422(00)86701-1. ISSN 0031-9422. Bibcode1977PChem..16..947M. https://www.sciencedirect.com/science/article/abs/pii/S0031942200867011. 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. https://www.sciencedirect.com/science/article/abs/pii/0163782780900028. Retrieved 25 April 2025.