Carpacin

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 (no longer recommended)
Identifiers
CAS Number	194605-01-1^Y
3D model (Jmol)	Interactive image Interactive image
ChemSpider	4445077^Y
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+^Y Key: OTRFVHWXENKCEG-ONEGZZNKSA-N^Y 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).
Y verify (what is ^YN ?)
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

↑ 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.
1 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. Archived from the original (PDF) on 2005-09-14.
↑ 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.

Types of phenylpropenes

Phenylpropenes	Anethole Apiole Asaricin Asarone Carpacin Chavibetol Chavicol Croweacin Dillapiole Elemicin Estragole Eugenol Exalatacin Isoapiole Isodillapiole Isoeugenol Isomyristicin Isosafrole Methyl eugenol Myristicin Nothosmyrnol Osmorhizole Safrole

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