:Prostanoic acid
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{{Chembox
| ImageFile = Prostanoic acid Structure.svg
| ImageSize =
| ImageName = Prostanoic Acid
| PIN = 7-[(1S,2S)-2-Octylcyclopentyl]heptanoic acid
|Section1={{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8504
| SMILES = CCCCCCCCC1CCCC1CCCCCCC(=O)O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 388714
| PubChem = 439642
| InChI = InChI=1S/C20H38O2/c1-2-3-4-5-6-9-13-18-15-12-16-19(18)14-10-7-8-11-17-20(21)22/h18-19H,2-17H2,1H3,(H,21,22)/t18-,19-/m0/s1
| InChIKey = WGJJROVFWIXTPA-OALUTQOASA-N
| CASNo_Ref = {{cascite|changed|CAS}}
| CASNo = 25151-81-9
}}
|Section2={{Chembox Properties
| C=20 | H=38 | O=2
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
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}}
Prostanoic acid (7-[(1S,2S)-2-octylcyclopentyl]heptanoic acid) is a saturated fatty acid which contains a cyclopentane ring. Its derivatives are prostaglandins - physiologically active lipid substances. Prostanoic acid is not found in nature, but it can be synthesized in vitro.
Synthesis
For the first time the synthesis of prostanoic acid from 1-formylcyclopentene was considered in detail in the scientific literature in 1975 by a group of French pharmacists.{{cite journal |author1=Hamon A |author2=Lacoume B |author3=Olivier A |author4=Pilgrim W.R. | title = Synthesis of prostanoic acid | journal = Tetrahedron Letters | volume = 16 | issue = 50 | pages = 4481–4482 | date = November 1975 | doi = 10.1016/S0040-4039(00)91098-0 }} One year later, a group of Japanese scientists, who worked in the central research laboratory of the "Sankyo Co., Ltd." company (Shinagawa, Tokyo), published another method for obtaining prostanoic acid from 2-[4-hydroxy-5-(methoxymethyl)cyclopent-2-en-1-yl] acetic acid.{{cite journal |vauthors=Sakai K, Inouye K, Nakamura N | title = Synthesis of (+)-prostanoic acid (1) | journal = Prostaglandins | volume = 12 | issue = 3 | pages = 399–401 | date = September 1976 | doi = 10.1016/0090-6980(76)90020-4 | pmid = 968053 }} In 1986, a group of Japanese scientists from Kyushu University in Fukuoka proposed their own scheme for obtaining prostanoic acid from limonene.{{cite journal |vauthors=Suemune H, Kawahara T, Sakai K | title = Conversion of limonene to prostanoic acid and 8-isoprostanoic acid | journal = Chemical and Pharmaceutical Bulletin | volume = 34 | issue = 2 | pages = 550–557 | date = February 1986 | doi = 10.1248/cpb.34.550 | doi-access = free }}
See also
References
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{{fatty acids}}
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