Chavicol

Structural formula
General
Surname	Chavicol (common name ); Allyl phenol; 4- (prop-2-en-1-yl) phenol ( IUPAC );
Molecular formula	C 9 H 10 O
External identifiers / databases
EC number	207-929-2
ECHA InfoCard	100.007.209
PubChem	68148
ChemSpider	21105856
Wikidata	Q2504388
properties
Molar mass	134.18 g mol −1
Physical state	liquid
density	1.0175 g cm −3
Melting point	16 ° C
boiling point	237 ° C
pK s value	10.23 (at 25 ° C)
Refractive index	1.5441
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Chavicol (synonymous with p -allylphenol) is a chemical compound from the group of phenylpropenes . It occurs naturally in the oil of basil and betel pepper . It also occurs in the oil of the bay .

properties

Betel pepper

Chavicol is found in betel pepper oil in a mass fraction of 30 to 40% next to terpenes , while in basil oil it occurs next to estragole (synonym methylchavicol). In the oil of the Bay it is present alongside eugenol . It occurs in smaller quantities in the oil of Ocimum canum . The biosynthesis takes place from p - coumaryl alcohol .

Chavicol is an attractant for the beetles Diabrotica undecimpunctata and Diabrotica virgifera . It has a weak antibacterial effect , with an MIC of 0.125% by volume against Aeromonas hydrophila and 2% by volume against Pseudomonas fluorescens .

Chavicol is used as a fragrance in perfumes , foods, and spirits .

literature

RG Atkinson: Phenylpropenes: Occurrence, Distribution, and Biosynthesis in Fruit. In: Journal of Agricultural and Food Chemistry . Volume 66, Number 10, March 2018, pp. 2259–2272, doi : 10.1021 / acs.jafc.6b04696 , PMID 28006900 .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Burkhard Fugmann: RÖMPP Encyclopedia Natural Products, 1st Edition, 2000. Georg Thieme Verlag, 2014, ISBN 978-3-131-79551-9 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ ^A ^b G. Vittorio Villavecchia: Nuovo Dizionario di Merceologia e Chimica Applicata . Volume 2, Hoepli, 1977, ISBN 88-203-0529-1 . P. 593.
^ Alfred Henry Allen: Commercial organic analysis: a treatise on the properties . Volume 2, Part 3, p. 358.
↑ NA Vyry Wouatsa, L. Misra, R. Venkatesh Kumar: Antibacterial activity of essential oils of edible spices, Ocimum canum and Xylopia aethiopica. In: Journal of Food science . Volume 79, Number 5, May 2014, pp. M972-M977, doi : 10.1111 / 1750-3841.12457 , PMID 24758511 .
↑ NPCs Board of Consultants & Engineers: The Complete Technology Book on Flavors, Fragrances and Perfumes. Niir Project Consultancy Services, 2007, ISBN 978-8-190-43988-6 , p. 89.
↑ DG Vassão, DR Gang, T. Koeduka, B. Jackson, E. Pichersky, LB Davin, NG Lewis: Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD (P) H-dependent reduction. In: Organic & biomolecular chemistry . Volume 4, Number 14, July 2006, pp. 2733-2744, doi : 10.1039 / b605407b , PMID 16826298 .
^ Wayne R. Bidlack: Phytochemicals as Bioactive Agents. CRC Press, 2000, ISBN 978-1-566-76788-0 , p. 106.

[Fugmann-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Burkhard Fugmann: RÖMPP Encyclopedia Natural Products, 1st Edition, 2000. Georg Thieme Verlag, 2014, ISBN 978-3-131-79551-9 .

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Villavecchia-3] A ^b G. Vittorio Villavecchia: Nuovo Dizionario di Merceologia e Chimica Applicata . Volume 2, Hoepli, 1977, ISBN 88-203-0529-1 . P. 593.

[4] Alfred Henry Allen: Commercial organic analysis: a treatise on the properties . Volume 2, Part 3, p. 358.

[5] NA Vyry Wouatsa, L. Misra, R. Venkatesh Kumar: Antibacterial activity of essential oils of edible spices, Ocimum canum and Xylopia aethiopica. In: Journal of Food science . Volume 79, Number 5, May 2014, pp. M972-M977, doi : 10.1111 / 1750-3841.12457 , PMID 24758511 .

[NPCS-6] NPCs Board of Consultants & Engineers: The Complete Technology Book on Flavors, Fragrances and Perfumes. Niir Project Consultancy Services, 2007, ISBN 978-8-190-43988-6 , p. 89.

[7] DG Vassão, DR Gang, T. Koeduka, B. Jackson, E. Pichersky, LB Davin, NG Lewis: Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD (P) H-dependent reduction. In: Organic & biomolecular chemistry . Volume 4, Number 14, July 2006, pp. 2733-2744, doi : 10.1039 / b605407b , PMID 16826298 .

[Bidlack-8] Wayne R. Bidlack: Phytochemicals as Bioactive Agents. CRC Press, 2000, ISBN 978-1-566-76788-0 , p. 106.