Plaunotol

Chemical compound From Wikipedia, the free encyclopedia

Plaunotol (18-hydroxygeranylgeraniol) is a chemical compound with the molecular formula C20H34O2. It is a diterpene that was first isolated from Croton sublyratus.[1]

Quick facts Names, Identifiers ...
Plaunotol
Names
IUPAC name
(2Z,6E)-2-[(3E)-4,8-Dimethylnona-3,7-dienyl]-6-methylocta-2,6-diene-1,8-diol
Other names
18-Hydroxygeranylgeraniol; Kelnac
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C20H34O2/c1-17(2)8-5-9-18(3)10-6-12-20(16-22)13-7-11-19(4)14-15-21/h8,10,13-14,21-22H,5-7,9,11-12,15-16H2,1-4H3/b18-10+,19-14+,20-13-
    Key: SUWYPNNPLSRNPS-UNTSEYQFSA-N
  • CC(=CCC/C(=C/CC/C(=C/CC/C(=C/CO)/C)/CO)/C)C
Properties
C20H34O2
Molar mass 306.490 g·mol−1
Pharmacology
Legal status
  • Rx in Japan
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Occurrence

Plaunotol has been identified as present in Croton sublyratus[1] and Croton stellatopilosus.[2] In plants, the compound is biosynthesized by hydroxylation of geranylgeraniol, a reaction which is catalyzed by the enzyme geranylgeraniol 18-hydroxylase.[3] A laboratory synthesis of plaunotol has been reported.[4]

Pharmacology

Plaunotol has antibacterial activity against Helicobacter pylori, the bacteria that causes gastric ulcers.[5] In Japan, plaunotol is used as a pharmaceutical drug under the trade name Kelnac for the treatment of gastritis and gastric ulcers.[6]

References

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