chaulmoogric acid
{{Chembox
| ImageFile = Chaulmoogric acid.svg
| ImageSize = 250px
| ImageAlt =
| IUPACName = 13-[(1S)-Cyclopent-2-en-1-yl]tridecanoic acid
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 29106-32-9
| ChEBI = 61391
| ChEMBL = 2204421
| ChemSpiderID = : 390179
| EC_number = 249-440-7
| KEGG = C08282
| PubChem = 441446
| UNII = 6TD35V6OLU
| SMILES = C(CCCCCCCCCCCC(O)=O)[C@H]1CCC=C1
| 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
| InChIKey = XMVQWNRDPAAMJB-QGZVFWFLSA-N
}}
| Section2 = {{Chembox Properties
| C = 18 | H = 32 | O = 2
| Appearance =
| Density =
| MeltingPtC = 68.5
| MeltingPt_notes = {{cite book | title = The Merck Index | edition = 11th | id = 2037. Chaulmoogric acid }}
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Chaulmoogric acid is a fatty acid found chaulmoogra oil, the oil from the seeds of Hydnocarpus wightianus.{{Cite journal | doi = 10.1002/jsfa.2740240606 | title = The component fatty acids of chaulmoogra oil | year = 1973 | last1 = Sengupta | first1 = A. | last2 = Gupta | first2 = J. K. | last3 = Dutta | first3 = J. | last4 = Ghosh | first4 = A. | journal = Journal of the Science of Food and Agriculture | volume = 24 | issue = 6 | pages = 669–74 | pmid = 4737104| bibcode = 1973JSFA...24..669S }} It is an unusual fatty acid which has a cyclopentene ring at its terminus instead of being entirely linear like most fatty acids.{{cite journal | doi = 10.1021/ja01619a038 | title = The Synthesis and Stereochemistry of Chaulmoogric Acid | date = 1955 | last1 = Mislow | first1 = Kurt | last2 = Steinberg | first2 = I. V. | journal = Journal of the American Chemical Society | volume = 77 | issue = 14 | pages = 3807–3810 }}
It is a white crystalline solid with a melting point of 68.5 °C. It is soluble in ether, chloroform, and ethyl acetate.
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.{{cite journal | title = The Chemotherapeutics of the Chaulmoogric Acid Series and Other Fatty Acids in Leprosy and Tuberculosis : I. Backtericidal Action; Active Principle; Specificity | author = Ernest Linwood Walker, Marion A. Sweeney | journal = The Journal of Infectious Diseases | volume = 26 | issue = 3 | date = 1920 | pages = 238–264 | doi = 10.1093/infdis/26.3.238 | jstor = 30084434 | url = https://zenodo.org/records/1860028/files/article.pdf }}