Isanolic acid
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| IUPAC name
8-hydroxyoctadec-17-en-9,11-diynoic acid
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| Other names
8-OH-18:3-delta-9a,11a,17
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C18H26O3 | |
| Molar mass | 290.403 g·mol−1 |
| Appearance | liquid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Isanolic 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 hydroxyl-OH in the position 8. The acid is one of the rare polyacetylenic acids with conjugated triple bonds.[1] The compound belongs to the family of diynes and enynes, as well as to the alkyne and alkenoic acids.
The related compounds are isanic and ketoisanic acids, both containing only one hydroxyl group.
Discovery
The acid was initially isolated in 1937 by researchers A. Steger and J. van Loon[2] from the seed oilof the tree Ongokea gore or Ongokea klaineana, a plant from equatorial Africa, called in the native language "boleka" or "isano"; a common name of isanolic acid comes from the latter.[3] They also discovered isanic acid. The oil seeds contain about 60% lipids.[4] Since the compound is hard to isolate, various analyses have revealed non-homogeneous data on the concentration of isanolic acid in isano oil: from 3%[5] to 44%[6] of the total fatty acids.
Chemical properties
The compound can be detected in isane oil together with other hydroxylated acetylenic fatty acids, all with the hydroxyl in position 8.[7][8]
The high degree of unsaturation suggests that oils with a high content of these conjugated acetylenic fatty acids are drying; the presence of hydroxylated fatty acids implies the possibility of forming atypical glycerides, such as triglycerides containing more than three acyl groups.[9]
Depending on the reaction conditions, isanolic acid reacts with phenol to form enol ethers or vinyl aromatics.[10]
References
- ^ Riley, J. P. (1951). "299. The seed oil of Onguekoa Gore engler. Part I. The position of the hydroxyl group in the unsaturated monohydroxy-C18 acid (or acids)". Journal of the Chemical Society (Resumed): 1346. doi:10.1039/jr9510001346. Retrieved 5 April 2025.
- ^ Steger, A.; van Loon, J. (January 1937). "Das fette Oel der Samen von Onguekoa Gore Engler". Fette und Seifen. 44 (6): 243–246. doi:10.1002/lipi.19370440608. Retrieved 5 April 2025.
- ^ Ullmann's Food and Feed, 3 Volume Set. John Wiley & Sons. 19 June 2017. p. 714. ISBN 978-3-527-33990-7. Retrieved 5 April 2025.
- ^ Black, H. K.; Weedon, B. C. L. (1953). "368. Unsaturated fatty acids. Part I. The synthesis of erythrogenic (isanic) and other acetylenic acids". Journal of the Chemical Society (Resumed): 1785–1793. doi:10.1039/JR9530001785. Retrieved 5 April 2025.
- ^ Miller, Roger W.; Weisleder, David; Kleiman, Robert; Plattner, Ronald D.; Smith, Cecil R. (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. Retrieved 5 April 2025.
- ^ Kaufmann, H. P.; Baltes, J.; Herminghaus, H. (January 1951). "Über das Boleko-Öl I: Die Fettsäuren des Öles und ihre Trennung". Fette und Seifen. 53 (9): 537–542. doi:10.1002/lipi.19510530908. Retrieved 5 April 2025.
- ^ Gunstone, F. D.; Sealy, A. J. (1963). "1101. Fatty acids. Part XII. The acetylenic acids of isano (boleko) oil". Journal of the Chemical Society (Resumed): 5772. doi:10.1039/jr9630005772. Retrieved 5 April 2025.
- ^ Morris, L. J. (1963). "1102. The oxygenated acids of isano (boleko) oil". Journal of the Chemical Society (Resumed): 5779. doi:10.1039/jr9630005779. Retrieved 5 April 2025.
- ^ Payne-Wahl, Kathleen; Plattner, Ronald D.; Spencer, Gayland F.; Kleiman, Robert (July 1979). "Separation of tetra-, penta-, and hexaacyl triglycerides by high performance liquid chromatography". Lipids. 14 (7): 601–605. doi:10.1007/bf02533443. Retrieved 5 April 2025.
- ^ Ravve, A.; Fitko, C. (1969). "A study on alkylation of phenol with isano oil". Journal of the American Oil Chemists' Society. 46 (6): 315–319. doi:10.1007/BF02545012. ISSN 1558-9331. Retrieved 5 April 2025.