Chaulmoogric acid

Chaulmoogric acid
Names
IUPAC name
13-[(1S)-Cyclopent-2-en-1-yl]tridecanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.044.931 Edit this at Wikidata
EC Number
  • 249-440-7
KEGG
UNII
  • InChI=1S/C18H32O2/c19-18(20)16-10-8-6-4-2-1-3-5-7-9-13-17-14-11-12-15-17/h11,14,17H,1-10,12-13,15-16H2,(H,19,20)/t17-/m1/s1
    Key: XMVQWNRDPAAMJB-QGZVFWFLSA-N
  • C(CCCCCCCCCCCC(O)=O)[C@H]1CCC=C1
Properties
C18H32O2
Molar mass 280.452 g·mol−1
Melting point 68.5 °C (155.3 °F; 341.6 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chaulmoogric acid is a fatty acid found chaulmoogra oil, the oil from the seeds of Hydnocarpus wightianus.[2] It is an unusual fatty acid which has a cyclopentene ring at its terminus instead of being entirely linear like most fatty acids.[3]

It is a white crystalline solid with a melting point of 68.5 °C.[1] It is soluble in ether, chloroform, and ethyl acetate.[1]

In the early 20th century, it was investigated as a possible treatment for leprosy due to the use in traditional medicine of chaulmoogra oil for leprosy.[4]

See also

References

  1. ^ a b c The Merck Index (11th ed.). 2037. Chaulmoogric acid.
  2. ^ Sengupta, A.; Gupta, J. K.; Dutta, J.; Ghosh, A. (1973). "The component fatty acids of chaulmoogra oil". Journal of the Science of Food and Agriculture. 24 (6): 669–74. Bibcode:1973JSFA...24..669S. doi:10.1002/jsfa.2740240606. PMID 4737104.
  3. ^ Mislow, Kurt; Steinberg, I. V. (1955). "The Synthesis and Stereochemistry of Chaulmoogric Acid". Journal of the American Chemical Society. 77 (14): 3807–3810. doi:10.1021/ja01619a038.
  4. ^ Ernest Linwood Walker, Marion A. Sweeney (1920). "The Chemotherapeutics of the Chaulmoogric Acid Series and Other Fatty Acids in Leprosy and Tuberculosis : I. Backtericidal Action; Active Principle; Specificity" (PDF). The Journal of Infectious Diseases. 26 (3): 238–264. doi:10.1093/infdis/26.3.238. JSTOR 30084434.
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