Helenynolic acid

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Helenynolic acid
Helenynolic acid.svg
Names
IUPAC name
(E,9S)-9-hydroxyoctadec-10-en-12-ynoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b14-11+/t17-/m1/s1
    Key: AUBZNAUZNGCKAN-GWKQRERASA-N
  • CCCCCC#CC=CC(CCCCCCCC(=O)O)O
Properties
C18H30O3
Molar mass 294.435 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Helenynolic acid is a hydroxylated and conjugated unsaturated fatty acid containing both a double and a triple bond. [1] [2] The acid belongs to the class of alkyne and alkenoic acids, as well as to the enynes. It is optically active with a negative rotation, i.e., levorotatory.

Contents

The delta notation is S-9-OH-18:2Δ10t,12a.

Discovery

The acid was initially isolated in 1965 from the glycerides of the seed oil of Helichrysum bracteatum of the Asteraceae family, by R. G. Powell and others. [3]

Helenynolic acid occurs in enantiomerically pure form in Xerochrysum bracteatum . [4] [5] In some seeds, heleninolic acid is formed by oxidation during storage, e.g., in those of Crepis vesicaria from the genus Crepis . [6]

The acid's presence has also been confirmed among the lipids of Helichrysum italicum .

Synthesis

Racemic heleninolic acid can be synthesized starting from methyl oleate. Ozonolysis of this methyl oleate yields methyl 9-oxononanoate. Its carbon chain is extended by acetylene and 1-bromohept-1-yne, thereby forming a compound with two triple bonds. One of the triple bonds is reduced using lithium aluminum hydride. [7]

Uses

Studies on helenynolic acid and related compounds frequently explore their possible therapeutic uses. Fatty acids containing distinct functional groups, such as hydroxy and alkyne groups, have been shown to possess anti-inflammatory, antimicrobial, and anticancer properties. These characteristics position them as promising options for creating novel medications or dietary supplements. [8]

References

  1. ↑ Senning, Alexander (30 October 2006). Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology. Elsevier. p. 179. ISBN   978-0-08-048881-3 . Retrieved 10 April 2025.
  2. ↑ "NCATS Inxight Drugs — HELENYNOLIC ACID". drugs.ncats.io. Retrieved 10 April 2025.
  3. ↑ Powell, R. G.; Smith, C. R. Jr.; Glass, C. A.; Wolff, I. A. (1 February 1965). "Helichrysum Seed Oil. II. Structure and Chemistry of a New Enynolic Acid1" . The Journal of Organic Chemistry . 30 (2): 610–615. doi:10.1021/jo01013a075. ISSN   0022-3263 . Retrieved 10 April 2025.
  4. ↑ Craig, J. Cymerman; Roy, S. K.; Powell, R. G.; Smith, C. R. Jr. (1 December 1965). "Optical Rotatory Dispersion and Absolute Configuration. VI. Structure and Absolute Configuration of Helenynolic Acid1" . The Journal of Organic Chemistry . 30 (12): 4342–4343. doi:10.1021/jo01023a522. ISSN   0022-3263 . Retrieved 10 April 2025.
  5. ↑ Powell, R. G.; Smith, C. R. Jr.; Glass, C. A.; Wolff, I. A. (1 February 1965). "Helichrysum Seed Oil. II. Structure and Chemistry of a New Enynolic Acid1" . The Journal of Organic Chemistry . 30 (2): 610–615. doi:10.1021/jo01013a075. ISSN   0022-3263 . Retrieved 10 April 2025.
  6. ↑ Spencer, G. F.; Earle, F. R.; Wolff, I. A.; Tallent, W. H. (1 February 1973). "Oxygenation of unsaturated fatty acids in seeds during storage" . Chemistry and Physics of Lipids. 10 (2): 191–202. doi:10.1016/0009-3084(73)90016-9. ISSN   0009-3084 . Retrieved 10 April 2025.
  7. ↑ Patrick, Timothy B.; Melm, Gerald F. (1 February 1979). "Naturally occurring acetylenes. 3. Synthesis of (.+-.)-helenynolic acid" . The Journal of Organic Chemistry . 44 (4): 645–646. doi:10.1021/jo01318a042. ISSN   0022-3263 . Retrieved 10 April 2025.
  8. ↑ "Helenynolic Acid Compound Overview". Ontosight.ai. Retrieved 10 April 2025.
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