Exocarpic acid

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Exocarpic acid
Exocarpic acid.svg
Names
IUPAC name
(E)-octadec-13-en-9,11-diynoic acid
Other names
Octadeca-trans-13-ene-9,11-diynoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1/C18H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-6H,2-4,11-17H2,1H3,(H,19,20)/b6-5+/f/h19H
    Key: ACHMRCSARDWYGC-AATRIKPKSA-N
  • C(CCCCCCCC#CC#C\C=C\CCCC)(=O)O
Properties
C18H26O2
Molar mass 274.404 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Sarcophyte sanguinea contains free exocarpic acid Sarcophyte sanguinea sanguinea 101303461.jpg
Sarcophyte sanguinea contains free exocarpic acid

Exocarpic acid is an unsaturated, conjugated fatty acid with one double bond and two triple bonds. It is isomeric to isanic acid and belongs to the class of alkyne and alkenoic acids, as well as the diynes and enynes. The acid's delta notation is 18:3-delta-9a,11a,13t. [1] Its structural formula is CH 3(CH2)3-CH=CH-C≡CC≡C-(CH2)7-COOH.

Contents

The acid was initially isolated in 1959, by H. H. Hatt and co-workers, from the roots of the Australian tree Exocarpos cupressiformis ; from this genus they derived the common name of exocarpic acid. [2]

Natural occurrence

Exocarpic acid is found in various plant species of the order Santalales .

In the family Olacaceae , it occurs, among others, in the seed oils of Curupira tefeensis [3] and Olax dissitiflora. [4] In the family Santalaceae , it occurs in several species of the genus Thesium , such as mountain flax and Thesium chinense, [5] as well as in several species of the genus Buckleya , such as Buckleya lanceolata [6] and Exocarpos sparteus . It also occurs in small amounts in the isano oil from Ongokea gore .

The parasitic plant Sarcophyte sanguinea from the family Balanophoraceae contains free (i.e., not present in the form of glycerides) exocarpic acid. [7]

Characteristics

Exocarpic acid exerts antibacterial activity against Mycobacterium tuberculosis by inhibiting the biosynthesis of mycolic acids. [8] [9] The acid also exerts antibacterial activity against several bacteria that cause oral infections. [5]

References

  1. ↑ Chow, Ching Kuang (12 November 1999). Fatty Acids in Foods and Their Health Implications. CRC Press. p. 10. ISBN   978-1-4200-0153-2 . Retrieved 9 April 2025.
  2. ↑ Hatt, H. H. (1 January 1959). "Acetylenic acids from fats of Santalaceae and Olacaceae: Seed and root oils of Exocarpus cupressiformis Labill" . Australian Journal of Chemistry . 12 (2): 190–195. doi:10.1071/CH9590190. ISSN   0004-9425 . Retrieved 9 April 2025.
  3. ↑ Spitzer, V.; Marx, F.; Maia, J. G.; Pfeilsticker, K. (1991). "Curupira tefeensis II: Occurrence of Acetylenic Fatty Acids" . Lipid / Fett. 93 (5): 169–174. doi:10.1002/lipi.19910930502. ISSN   1521-4133 . Retrieved 9 April 2025.
  4. ↑ Mavundza, E. J.; Chukwujekwu, J. C.; Maharaj, R.; Finnie, J. F.; Van Heerden, F. R.; Van Staden, J. (1 January 2016). "Identification of compounds in Olax dissitiflora with larvacidal effect against Anopheles arabiensis". South African Journal of Botany . 102: 1–3. Bibcode:2016SAJB..102....1M. doi: 10.1016/j.sajb.2015.06.013 . ISSN   0254-6299.
  5. 1 2 Liu, Chang; Li, Xiao-Tian; Cheng, Rong-Rong; Han, Zhu-Zhen; Yang, Li; Song, Zhong-Chen; Wang, Zheng-Tao (1 March 2018). "Anti-oral common pathogenic bacterial active acetylenic acids from Thesium chinense Turcz" . Journal of Natural Medicines. 72 (2): 433–438. doi:10.1007/s11418-018-1180-3. ISSN   1861-0293. PMID   29435792 . Retrieved 9 April 2025.
  6. ↑ Hopkins, C. Y.; Chisholm, Mary J.; Cody, W. J. (1 January 1969). "Fatty acid components of some Santalaceae seed oils" . Phytochemistry . 8 (1): 161–165. Bibcode:1969PChem...8..161H. doi:10.1016/S0031-9422(00)85808-2. ISSN   0031-9422 . Retrieved 9 April 2025.
  7. ↑ Naidoo Siegfried E.^Drewes, Lovina A. C.; Staden, J. Van; Hutchings, Anne (1 January 1992). "Exocarpic acid and other compounds from tubers and inflorescences of Sarcophyte sanguinea" . Phytochemistry . 31 (11): 3929–3931. Bibcode:1992PChem..31.3929N. doi:10.1016/S0031-9422(00)97556-3. ISSN   0031-9422 . Retrieved 9 April 2025.
  8. ↑ Hydroxy Acids—Advances in Research and Application: 2012 Edition. ScholarlyEditions. 26 December 2012. ISBN   978-1-4816-0039-2 . Retrieved 9 April 2025.
  9. ↑ Koch, Michael; Bugni, Tim S.; Sondossi, Mohammad; Ireland, Chris M.; Barrows, Louis R. (October 2010). "Exocarpic Acid Inhibits Mycolic Acid Biosynthesis in Mycobacterium tuberculosis" . Planta Medica . 76 (15): 1678–1682. Bibcode:2010PlMed..76.1678K. doi:10.1055/s-0030-1249939. ISSN   0032-0943. PMID   20506078 . Retrieved 9 April 2025.
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