Nothoapiole

Last updated
Nothoapiole
Nothoapiole.svg
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
3D model (JSmol)
ChemSpider
PubChem CID
  • 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 Yes check.svgY
    Key: IWGPXDGGZYMDJF-UHFFFAOYSA-N Yes check.svgY
  • 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
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).

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]

See also

References

  1. ↑ 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.
  2. ↑ Mathela, Chandra S.; Joshi, Rakesh K.; Bisht, Balam S.; Joshi, Subhash C. (1 June 2015). "Nothoapiole and α-Asarone Rich Essential Oils from Himalayan Pleurospermum angelicoides Benth" (PDF). Records of Natural Products. 9 (4): 546–552 – via ACG Publications.
  3. ↑ Kapoor, Inder Pal Singh; Singh, Bandana; Singh, Gurdip; De Heluani, Carola S; De Lampasona, Marina P.; Catalan, Cesar A N (2010). "Chemistry and antioxidant activity of essential oil and oleoresins of black caraway (Carum bulbocastanum) fruits: Part 69". Journal of the Science of Food and Agriculture. 90 (3): 385–390. doi:10.1002/jsfa.3824. ISSN   1097-0010.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
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