:Carpacin

{{chembox

| Watchedfields = changed

| verifiedrevid = 399708366

| ImageFile = carpacin.png

| ImageSize = 200px

| ImageAlt = Skeletal formula

| ImageFile1 = Carpacin-3D-balls.png

| ImageSize1 = 210

| ImageAlt1 = Ball-and-stick model

| PIN = 5-Methoxy-6-[(E)-prop-1-enyl]-2H-1,3-benzodioxole{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/5281763#section=IUPAC-Name&fullscreen=true | title=Carpacin }}

| OtherNames = (E)-5-Methoxy-6-(prop-1-en-1-yl)benzo[d][1,3]dioxole
(E)-2-Methoxy-4,5-methylenedioxypropenylbenzene

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4445077

| 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+

| InChIKey = OTRFVHWXENKCEG-ONEGZZNKBF

| SMILES1 = O1c2cc(c(OC)cc2OC1)/C=C/C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OTRFVHWXENKCEG-ONEGZZNKSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 194605-01-1

| CASNo1_Ref = {{cascite|correct|CAS}}

| CASNo1 = 56767-00-1

| CASNo1_Comment = (non-specific)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Z52RCE6A8B

| PubChem = 5281763

| SMILES = C/C=C/C1=CC(OCO2)=C2C=C1OC

}}

|Section2={{Chembox Properties

| C=11 | H=12 | O=3

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|Section3={{Chembox Hazards

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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.{{cite journal | title = Essential oils of the genus Crowea (Rutaceae) |author1= Brophy, Joseph J. |author2=Goldsack, Robert J. |author3=Punruckvong, Acharaporn |author4=Forster, Paul I. |author5=Fookes, Christopher J.R. | journal = Journal of Essential Oil Research | date = 1997 | volume = 9 | issue = 4 | pages = 401–409|doi= 10.1080/10412905.1997.9700740 }}

Carpacin is a biosynthetic precursor of the more complex lignan-dimer, carpanone.{{cite journal|doi=10.1071/CH9691803|title=Trans-2-methoxy-4,5-methylenedioxypropenylbenzene (carpacin) from a Cinnamomum sp. from Bougainville|author1=J. Mohandas |author2=M. Slaytor |author3=T.R. Watson |journal=Aust. J. Chem.|year=1969|volume=22|pages=1803–1804|issue=8|doi-access=free}} It is classified as a phenylpropanoid.

Carpacin has been prepared synthetically from sesamol{{cite journal |journal=Journal of the Chinese Chemical Society |year=2000 |volume=47 |issue=5 |pages=1165–1169 |title=Total Synthesis of Carpacin and Its Geometric Isomer as a Cancer Chemopreventer |author1=Tsui-Hwa Tseng |author2=Yen-Min Tsheng |author3=Yean-Jang Lee |author4=Hsing-Ling Hsu |url=http://www.sinica.edu.tw/~ccswww/zj-OR-2000-P1165.PDF |url-status=dead |archiveurl=https://web.archive.org/web/20050914061935/http://www.sinica.edu.tw/~ccswww/zj-OR-2000-P1165.PDF |archivedate=2005-09-14 |doi=10.1002/jccs.200000157 }} and has been studied for potential use as an insecticide{{cite journal|author1=BH Alexander |author2=SI Gertler |author3=RT Brown |author4=TA Oda |author5=M Beroza |journal=J. Org. Chem.|year=1959|volume=24|pages=1504|title=Synthesis of Methylenedioxyphenyl Compounds from Isosafrole and Sesamol|doi=10.1021/jo01092a029|issue=10 }} and inhibitor of carcinogenesis.