Nothoapiole

Nothoapiole
Names
	Preferred IUPAC name 4,5,7-Trimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole
	Other names 2,3,6-Trimethoxy,4,5-methylenedioxy-allylbenzene; 1,3-Benzodioxole, 4,5,7-trimethoxy-6-(2-propen-1-yl)-
Identifiers
CAS Number	22934-74-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	161286 ;
PubChem CID	185518;
CompTox Dashboard (EPA)	DTXSID30945617 ;
	InChI InChI=1S/C13H16O5/c1-5-6-8-9(14-2)11(16-4)13-12(10(8)15-3)17-7-18-13/h5H,1,6-7H2,2-4H3 Key: IWGPXDGGZYMDJF-UHFFFAOYSA-N ; InChI=1S/C13H16O5/c1-5-6-8-9(14-2)11(16-4)13-12(10(8)15-3)17-7-18-13/h5H,1,6-7H2,2-4H3;
	SMILES COC1=C(C(=C(C2=C1OCO2)OC)OC)CC=C;
Properties
Chemical formula	C13H16O5
Molar mass	252.266 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Nothoapiole is a phenylpropene, a natural organic compound present in the essential oil of Perilla frutescens from Jeju Island in Korea^[1] and the major component of the essential oil obtained from the roots of Pleurospermum angelicoides Benth.^[2] It is also found in the essential oil of black caraway (Carum bulbocastanum) fruits^[3] and Carum nigrum.^[4]

This highly oxygenated phenylpropanoid, previously reported in a few Carum species, is structurally and biogenetically related to myristicin, apiole and dillapiole.^[5]^[6]

References

^ Ito, Michiho; Toyoda, Mariko; Yuba, Akiko; Honda, Gisho (1999). "Genetic Analysis of Nothoapiol Formation in Perilla frutescens". Biological & Pharmaceutical Bulletin. 22 (6): 598–601. doi:10.1248/bpb.22.598. PMID 10408233.
^ http://www.acgpubs.org/RNP/2015/Volume9/Issue%201/67-RNP-EO_1202-015.pdf ^{[bare URL PDF]}
^ Journal of the Science of Food and Agriculture Volume 90, Issue 3, pages 385–390, February 2010
^ Singh, Gurdip; Marimuthu, Palanisamy; De Heluani, Carola S.; Catalan, Cesar A. N. (2006). "Antioxidant and Biocidal Activities of Carum nigrum(Seed) Essential Oil, Oleoresin, and Their Selected Components†". Journal of Agricultural and Food Chemistry. 54 (1): 174–81. Bibcode:2006JAFC...54..174S. doi:10.1021/jf0518610. hdl:11336/99544. PMID 16390196.
^ H. Laouer; E.K. Meriem; S. Prado; N. Baldovini (2009). "An antibacterial and antifungal phenylpropanoid from Carum montanum (Coss. et Dur.) Benth. et Hook". Phytother. Res. 23 (12): 1726–1730. doi:10.1002/ptr.2820. PMID 19370550. S2CID 2668369.
^ M. Ito; M. Toyoda; A. Yuba; G. Honda (1999). "Genetic analysis of nothoapiole formation in Perilla frutescens". Biol. Pharm. Bull. 22 (6): 598–601. doi:10.1248/bpb.22.598. PMID 10408233.