Hiragonic acid

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Hiragonic acid
Hiragonic acid.png
Names
IUPAC name
(6E,10E,14E)hexadeca-6,10,14-trienoic acid
Other names
C16:3n-2,6,10
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C16H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-3,6-7,10-11H,4-5,8-9,12-15H2,1H3,(H,17,18)/b3-2+,7-6+,11-10+
    Key: ZKCRKOCVERWCLP-DJWHJZFYSA-N
  • CC=CCCC=CCCC=CCCCCC(=O)O
Properties
C16H26O2
Molar mass 250.382 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Hiragonic acid is a linear fatty acid with 16 carbon atoms and three double bonds in the trans-configuration. [1] [2] The compound is also a polyunsaturated carboxylic acid; its molecular formula is C16H26O2.

Contents

Discovery and natural occurrence

The acid was identified in 1929 by Japanese researchers Yoshiyuki Toyama and Tomotaro Tsuchyia [3] in the oil of Japanese sardine (Clupanodon melanostica). [4] In 1935, its structure was clarified by the same researchers [5] who also proposed the current name—derived from the Japanese word for sardine: hirago. [6] The acid was subsequently isolated in the oil of bonito and in the red alga Hypnea musciformis. [7]

Some studies have identified hiragonic acid in Pongamia pinnata seed oil. [8]

Properties

At room temperature between 4 °C and 20 °C, the acid forms a yellow liquid with a density of 0.9288 g/cm³ and a refractive index of 1.4855 at 20 °C. The compound is soluble in acetone, ethanol, diethyl ether, and methanol. [9]

There are doubts about the all-trans configuration of hiragonic acid. Some authors attribute the name "hiragonic acid" to other positional or cis-isomers of hexadecatrienoic acid. [10] [11]

References

  1. ↑ Eastwood, Martin (5 June 2013). Principles of Human Nutrition. John Wiley & Sons. ISBN   978-1-118-76053-6 . Retrieved 4 June 2025.
  2. ↑ "Trivial names of fatty acids-Part 1 – AOCS". aocs.org. Retrieved 4 June 2025.
  3. ↑ Borgstrom, Georg (2 December 2012). Fish As Food V1: Production, Biochemistry,and Microbiology. Elsevier. ISBN   978-0-323-14280-9 . Retrieved 4 June 2025.
  4. ↑ Toyama, Yoshiyuki; Tsuchiya, Totnotaro (1 April 1929). "UEBER DIE HOCHUNGESÄTTIGTEN SÄUREN DES SARDINENÖLS. I. MITTEILUNG: EINE NEUE SÄURE C16H26O2 AND DIE HOCHUNGESÄTTIGTEN C18— SÄUREN". Bulletin of the Chemical Society of Japan . 4 (4): 83–91. doi:10.1246/bcsj.4.83. ISSN   0009-2673 . Retrieved 4 June 2025.
  5. ↑ Toyama, Yoshiyuki; Tsuchiya, Tomotaro (1 May 1935). "The Highly Unsaturated Acids in Sardine Oil. Ii. The Constitution of Hiragonic Acid C16H26O2". Bulletin of the Chemical Society of Japan . 10 (5): 192–199. doi:10.1246/bcsj.10.192. ISSN   0009-2673 . Retrieved 4 June 2025.
  6. ↑ The Etymology of Chemical Names: Tradition and Convenience vs. Rationality in Chemical Nomenclature. Walter de Gruyter GmbH & Co KG. 8 October 2019. ISBN   978-3-11-061124-3 . Retrieved 4 June 2025.
  7. ↑ Blunt, John W.; Munro, Murray H. G. (19 September 2007). Dictionary of Marine Natural Products. CRC Press. p. H-258. ISBN   978-1-040-22179-2 . Retrieved 4 June 2025.
  8. ↑ Shameel, S.; Usmanghani, K.; Ali, M. S.; Ahmad, V. U. (January 1996). "Chemical constituents from the seeds of Pongamia pinnata (L.) Pierre". Pakistan Journal of Pharmaceutical Sciences . 9 (1): 11–20. ISSN   1011-601X. PMID   16414771.
  9. ↑ Ralston, A. W. (1948). Fatty Acids and Their Derivatives. New York: John Wiley and Sons . Retrieved 5 June 2025.
  10. ↑ "Trivial names of fatty acids-Part 1 – AOCS". aocs.org. Retrieved 9 June 2025.
  11. ↑ "LIPID MAPS". lipidmaps.org. Retrieved 9 June 2025.
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