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Prostanoic acid

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Prostanoic acid
Prostanoic Acid
Names
Preferred IUPAC name 7-heptanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
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/s1Key: WGJJROVFWIXTPA-OALUTQOASA-N
SMILES
  • CCCCCCCCC1CCCC1CCCCCCC(=O)O
Properties
Chemical formula C20H38O2
Molar mass 310.522 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Prostanoic acid (7-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. 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- acetic acid. In 1986, a group of Japanese scientists from Kyushu University in Fukuoka proposed their own scheme for obtaining prostanoic acid from limonene.

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.
Lipids: fatty acids
Saturated
ω−3 Unsaturated
ω−5 Unsaturated
ω−6 Unsaturated
ω−7 Unsaturated
ω−9 Unsaturated
ω−10 Unsaturated
ω−11 Unsaturated
ω−12 Unsaturated


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