Prostanoic acid

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Prostanoic acid
Prostanoic Acid
Names
Preferred IUPAC name
7-[(1S,2S)-2-Octylcyclopentyl]heptanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • 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
    Key: WGJJROVFWIXTPA-OALUTQOASA-N
  • CCCCCCCCC1CCCC1CCCCCCC(=O)O
Properties
C20H38O2
Molar mass 310.522 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1] 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.[2] In 1986, a group of Japanese scientists from Kyushu University in Fukuoka proposed their own scheme for obtaining prostanoic acid from limonene.[3]

See also

References

  1. ^ Hamon A; Lacoume B; Olivier A; Pilgrim W.R. (November 1975). "Synthesis of prostanoic acid". Tetrahedron Letters. 16 (50): 4481–4482. doi:10.1016/S0040-4039(00)91098-0.
  2. ^ Sakai K, Inouye K, Nakamura N (September 1976). "Synthesis of (+)-prostanoic acid (1)". Prostaglandins. 12 (3): 399–401. doi:10.1016/0090-6980(76)90020-4. PMID 968053.
  3. ^ Suemune H, Kawahara T, Sakai K (February 1986). "Conversion of limonene to prostanoic acid and 8-isoprostanoic acid". Chemical and Pharmaceutical Bulletin. 34 (2): 550–557. doi:10.1248/cpb.34.550.


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