Carpacin

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Carpacin
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
5-Methoxy-6-[(1E)-prop-1-en-1-yl]-2H-1,3-benzodioxole
Other names
(E)-5-Methoxy-6-(prop-1-en-1-yl)benzo[d][1,3]dioxole
(E)-2-Methoxy-4,5-methylenedioxypropenylbenzene (no longer recommended)
Identifiers
194605-01-1 YesY
ChemSpider 4445077 YesY
Jmol 3D model Interactive image
Interactive image
PubChem 5281763
Properties
C11H12O3
Molar mass 192.21
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Carpacin is a naturally occurring organic compound first isolated from the Carpano tree (an unidentified Cinnamomum species of the family Lauraceae which is native to Bougainville Island), from which it derives its name. It is a biosynthetic precursor of the more complex lignan-dimer, carpanone.[1] Carpacin is classified as a phenylpropanoid.

Carpacin has been prepared synthetically from sesamol[2] and has been studied for potential use as an insecticide,[3] an antidepressant, and an inhibitor of carcinogenesis.[2]

References[edit]

  1. ^ J. Mohandas; M. Slaytor; T.R. Watson (1969). "Trans-2-methoxy-4,5-methylenedioxypropenylbenzene (carpacin) from a Cinnamomum sp. from Bougainville". Aust. J. Chem. 22 (8): 1803–1804. doi:10.1071/CH9691803. 
  2. ^ a b Tsui-Hwa Tseng; Yen-Min Tsheng; Yean-Jang Lee; Hsing-Ling Hsu (2000). "Total Synthesis of Carpacin and Its Geometric Isomer as a Cancer Chemopreventer" (PDF). Journal of the Chinese Chemical Society. 47: 1165–1169. 
  3. ^ BH Alexander; SI Gertler; RT Brown; TA Oda; M Beroza (1959). "Synthesis of Methylenedioxyphenyl Compounds from Isosafrole and Sesamol". J. Org. Chem. 24 (10): 1504. doi:10.1021/jo01092a029.