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 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	4445077 ;
PubChem CID	5281763;
CompTox Dashboard (EPA)	DTXSID801027180 ;
	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). verify (what is ?) 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.
^ ^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. Archived from the original (PDF) on 2005-09-14. {{cite journal}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
^ 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.

Template:Natural phenol-stub

[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.

[Tseng-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. {{cite journal}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)

[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.

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