Carpacin

Carpacin

Names
IUPAC name (E)-2-Methoxy-4,5-methylenedioxypropenylbenzene
Identifiers
CAS Number	194605-01-1
ChemSpider	4445077
Jmol interactive 3D	Image Image
PubChem	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	192.21
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 naturally occurring organic compound first isolated from the Carpano tree (Cinnamomum sp.), 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

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. 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.