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
ChemSpider
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
Y Key: IWGPXDGGZYMDJF-UHFFFAOYSA-N
Y 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
COC1=C(C(=C(C2=C1OCO2)OC)OC)CC=C
Properties
C 13 H 16 O 5
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).
Chemical compound
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]
^ 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. 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 .