Carpacin

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 also found in essential oils of the genus Crowea.[1]

Carpacin

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
Identifiers
CAS Number	194605-01-1
3D model (JSmol)	Interactive image Interactive image
ChemSpider	4445077
PubChem CID	5281763
InChI 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+ Key: OTRFVHWXENKCEG-ONEGZZNKSA-N 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
SMILES C/C=C/C1=CC(OCO2)=C2C=C1OC O1c2cc(c(OC)cc2OC1)/C=C/C
Properties
Chemical formula	C11H12O3
Molar mass	192.214 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Carpacin is a biosynthetic precursor of the more complex lignan-dimer, carpanone.[2] It is classified as a phenylpropanoid.

Carpacin has been prepared synthetically from sesamol[3] and has been studied for potential use as an insecticide[4] and inhibitor of carcinogenesis.[3]

References

1. 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.
2. 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.
3. 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 (5): 1165–1169. doi:10.1002/jccs.200000157. Archived from the original (PDF) on 2005-09-14.
4. 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.