Isanic acid
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| Names | |
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| IUPAC name
octadec-17-en-9,11-diynoic acid
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| Other names
Erythrogenic acid
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C18H26O2 | |
| Molar mass | 274.404 g·mol−1 |
| Appearance | crystalline platelets or prisms, light-sensitive; turns red |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isanic acid or erythrogenic acid is a linear fatty acid composed of 18 carbon atoms, with two triple bonds in the positions 9≡10 and 11≡12 and a double bond in the position 17=18. This is one of the rare polyacetylenic acids with conjugated triple bonds. Its delta notation is 18:3Δ9a,11a,17. Its structural formula is CH2=CH-(CH2)4–C≡C–C≡C–(CH2)7–COOH.[1]
Exocarpic acid is isomeric to isanic acid. The related isanolic acid, unlike isanic acid, contains an additional hydroxyl group. The oxygenated isanic acid is called ketoisanic acid.
Discovery
[edit | edit source]Isanic acid was initially isolated in 1937 by researchers A. Steger and J. van Loon[2] in the oil of the seeds of Ongokea gore or Ongokea klaineana, a plant from equatorial Africa, called in the native language "boleka" or "isane", hence the common name of isanic acid.[3][4] The oil seeds contain about 60% lipids.[5] Various analyses have revealed the concentration of isanic acid in isane oil from 32% to 51%.
Synthesis
[edit | edit source]The synthesis of isanic acid is possible starting from 10-undecynoic acid.[5]
Physical properties
[edit | edit source]Isanic acid can be detected together with its isomers with the double bond in position 13=14: boletic acid and exocarpic acid, and hydroxylated fatty acids, such as isanolic acid.
The high degree of unsaturation suggests that oils with a high content of these conjugated acetylenic fatty acids are drying. Isanic acid polymerizes easily,[6] turning a bright red color when exposed to light. Because of this characteristic the alternative name of erythrogenic acid was proposed by Castille in 1940.[5]
Insoluble in ether.[7]
References
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