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Carpacin

From Wikipedia, the free encyclopedia
Carpacin
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
5-Methoxy-6-[(E)-prop-1-enyl]-2H-1,3-benzodioxole[1]
Other names
(E)-5-Methoxy-6-(prop-1-en-1-yl)benzo[d][1,3]dioxole
(E)-2-Methoxy-4,5-methylenedioxypropenylbenzene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C11H12O3/c1-3-4-8-5-10-11(14-7-13-10)6-9(8)12-2/h3-6H,7H2,1-2H3/b4-3+ checkY
    Key: OTRFVHWXENKCEG-ONEGZZNKSA-N checkY
  • InChI=1/C11H12O3/c1-3-4-8-5-10-11(14-7-13-10)6-9(8)12-2/h3-6H,7H2,1-2H3/b4-3+
    Key: OTRFVHWXENKCEG-ONEGZZNKBF
  • C/C=C/C1=CC(OCO2)=C2C=C1OC
  • O1c2cc(c(OC)cc2OC1)/C=C/C
Properties
C11H12O3
Molar mass192.214 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Carpacin is a naturally occurringorganic compound first isolated from the Carpano tree (an unidentifiedCinnamomum species of the familyLauraceae which is native toBougainville Island), from which it derives its name. It is also found inessential oils of the genusCrowea.[2]

Carpacin is abiosynthetic precursor of the more complexlignan-dimer,carpanone.[3] It is classified as aphenylpropanoid.

Carpacin has been prepared synthetically fromsesamol[4] and has been studied for potential use as aninsecticide[5] and inhibitor ofcarcinogenesis.[4]

References

[edit]
  1. ^"Carpacin".
  2. ^Brophy, Joseph J.; Goldsack, Robert J.; Punruckvong, Acharaporn; Forster, Paul I.; Fookes, Christopher J.R. (1997). "Essential oils of the genus Crowea (Rutaceae)".Journal of Essential Oil Research.9 (4):401–409.doi:10.1080/10412905.1997.9700740.
  3. ^J. Mohandas; M. Slaytor; T.R. Watson (1969)."Trans-2-methoxy-4,5-methylenedioxypropenylbenzene (carpacin) from aCinnamomum sp. from Bougainville".Aust. J. Chem.22 (8):1803–1804.doi:10.1071/CH9691803.
  4. ^abTsui-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 (5):1165–1169.doi:10.1002/jccs.200000157. Archived fromthe original(PDF) on 2005-09-14.
  5. ^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.
Phenylpropenes
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