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W312401

Sigma-Aldrich

Vanillylacetone

≥96%, FG

Synonym(s):

Zingerone

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About This Item

Linear Formula:
4-(HO)C6H3-3-(OCH3)CH2CH2COCH3
CAS Number:
122-48-5
Molecular Weight:
194.23
FEMA Number:
3124
EC Number:
204-548-3
Council of Europe no.:
139
MDL number:
MFCD00048232
UNSPSC Code:
12164502
PubChem Substance ID:
24901474
Flavis number:
7.005
NACRES:
NA.21

biological source

synthetic

grade

FG
Fragrance grade
Halal

Agency

follows IFRA guidelines
meets purity specifications of JECFA

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 184.1099

Assay

≥96%

refractive index

n20/D 1.541 (lit.)

bp

141 °C/0.5 mmHg (lit.)

mp

40-41 °C (lit.)

density

1.14 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

Organoleptic

ginger; woody; spicy; phenolic; sweet; vanilla

storage temp.

2-8°C

SMILES string

COc1cc(CCC(C)=O)ccc1O

InChI

1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3

InChI key

OJYLAHXKWMRDGS-UHFFFAOYSA-N

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General description

Vanillylacetone is one of the key aroma constituents of ginger. It is a pharmacologically active compound that may contribute to the anti-inflammatory, anti-oxidant, anti-cancerous, radioprotective and anti-microbial properties of ginger.

Application

Vanillylacetone can be used as a food additive in food industries because of its sweet and spicy flavor.

Biochem/physiol Actions

Taste at 20 ppm in 5%

Other Notes

Natural occurrence: Cranberry and ginger.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jaw-Chyun Chen et al.
Journal of agricultural and food chemistry, 55(21), 8390-8397 (2007-09-21)
Ginger is one of the most commonly used fresh herbs and spices. Enterotoxigenic Escherichia coli heat-labile enterotoxin (LT)-induced diarrhea is the leading cause of infant death in developing countries. In this study, we demonstrated that ginger significantly blocked the binding
Vanillylacetone attenuates NLRP3 inflammasome mediated immune responses in murine bone marrow derived macrophages via NLRP3 alkylation
Kim Han-Bi, et al.
Journal of functional foods, 64, 103655-103655 (2020)
Sangpill Hwang et al.
Chemosphere, 72(4), 572-577 (2008-05-13)
When 4-(4-hydroxy-3-methoxy-phenyl)-2-butanone (vanillylacetone) was tested for manganese peroxidase (MnP)-catalyzed oxidation, it was found to be degraded with the cleavage of an aromatic ring. Among numerous products of vanillylacetone oxidation, four major ones were purified by thin-layer chromatography and identified using
Bhuvanagiri Nageshwar Rao et al.
European journal of pharmacology, 657(1-3), 59-66 (2011-02-22)
Zingerone a dietary compound was investigated for its ability to protect against radiation induced genotoxicity and apoptosis in human lymphocytes growing in vitro. The radiation antagonistic potential of zingerone was assessed by alkaline comet, cytokinesis-block micronucleus, apoptosis and reactive oxygen
Li-Kun Han et al.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 128(8), 1195-1201 (2008-08-02)
We reported that ginger prevented obesity in mice fed a high-fat diet in previous study. In this experiment, we examined the effects of zingerone, the major pungent component of ginger on fat storage in ovariectomized (Ovx) rats. Oral administration of
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