Vanillylacetone

Structural formula
General
Surname	Vanillylacetone
other names	Zingeron Zingiberon 4- (4-hydroxy-3-methoxyphenyl) -2-butanone FEMA  3124 ZINGERONE ( INCI )
Molecular formula	C 11 H 14 O 3
Brief description	colorless solid
External identifiers / databases
CAS number 122-48-5 EC number 204-548-3 ECHA InfoCard 100.004.136 PubChem 31211 ChemSpider 28952 Wikidata Q1064625
properties
Molar mass	194.23 g mol −1
Physical state	firmly
density	1.14 g cm −3 (25 ° C)
Melting point	40-41 ° C
boiling point	141 ° C (0.7 hPa)
solubility	slightly soluble in water soluble in ether and dilute alkalis
Refractive index	1.541 (20 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	2580 mg kg −1 ( LD 50 ,  rat ,  oral ) > 5000 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
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

Vanillylacetone is a chemical compound from the group of ketones .

Occurrence

Cowberry ( Vaccinium vitis-idaea )

Vanillylaceton occurs naturally in cranberries and ginger before. The compound was first isolated from ginger in 1917 by the Japanese chemist Hiroshi Nomura . It is the hot substance in ginger oleoresin .

Extraction and presentation

Vanillylaceton 4 can be achieved by aldol condensation of vanillin 1 and acetone 2 to 4- (4-hydroxy-3-methoxyphenyl) -3-buten-2-one 3 and subsequent catalytic hydrogenation be obtained.

The compound is also formed from gingerol through a retroaldol reaction.

properties

Vanillylacetone is a colorless solid with a pungent taste that is sparingly soluble in water. Vanillylacetone is one of the most important flavor components of ginger. It is a pharmacologically active ingredient that can contribute to the anti-inflammatory, antioxidant, anti-cancer, radioprotective, and antimicrobial properties of ginger.

use

Vanillylacetone is used as a flavoring agent.

Individual evidence

1. ^ Entry on FEMA 3124 in the database of the Flavor and Extract Manufacturers Association of the United States .
2. ↑ Entry on ZINGERONE in the CosIng database of the EU Commission, accessed on July 10, 2020.
3. ↑ ^{a b} Data sheet 4- (4-Hydroxy-3-methoxyphenyl) -2-butanone, 97% from AlfaAesar, accessed on March 8, 2019 ( PDF )(JavaScript required) .
4. ↑ ^{a b c d e f g h i j k} data sheet Vanillylaceton, ≥96%, FG at Sigma-Aldrich , accessed on March 8, 2019 ( PDF ).
5. ↑ ^{a b c d} Entry on Zingeron. In: Römpp Online . Georg Thieme Verlag, accessed on March 8, 2019.
6. ↑ Hiroshi Nomura: LXIV. — The pungent principles of ginger. Part I. A new ketone, zingerone (4-hydroxy-3-methoxyphenylethyl methyl ketone) occurring in ginger. In: J. Chem. Soc., Trans. 111, 1917, pp. 769-776, doi : 10.1039 / CT9171100769 .
7. ↑ External identifiers of or database links to 4- (4-Hydroxy-3-methoxyphenyl) -3-buten-2-one : CAS number: 1080-12-2, PubChem : 5354238 , ChemSpider : 4510464 , Wikidata : Q81989495 .
8. ↑ ^{a b} Entry on Vanillylacetone in the Hazardous Substances Data Bank , accessed March 8, 2019.
9. ↑ R. Hansel, O. Sticher, E. Steinegger: Pharmakognosie - Phytopharmazie . Springer-Verlag, 2013, ISBN 978-3-662-09269-9 , pp. 658 ( limited preview in Google Book search).
10. ↑ Bilal Ahmad, Muneeb U. Rehman et al. a .: A Review on Pharmacological Properties of Zingerone (4- (4-Hydroxy-3-methoxyphenyl) -2-butanone). In: The Scientific World Journal . 2015, 2015, p. 1, doi : 10.1155 / 2015/816364 .