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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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Recent update on multiple pharmacological benefits of zingerone: a quick review.
Kumar L, et al.
American Journal of Phytomedicine and Clinical Therapeutics, 2, 693-704 (2014)
Momoe Iwami et al.
Biomedical research (Tokyo, Japan), 32(2), 181-185 (2011-05-10)
Zingerone, a pungent component of ginger, may exert beneficial therapeutic effects on hypermotility-induced diarrhea because it has the ability to inhibit contractions of colonic smooth muscles. However, the pungency is undesirable for possible therapeutic use. The purpose of this study
Yueh-Ping Chang et al.
Fish & shellfish immunology, 32(2), 284-290 (2011-12-17)
Zingerone, one of the active components of ginger, is a phenolic alkanone with antioxidant and anti-inflammatory properties. The effects of zingerone supplementation on the growth, immunity, and disease resistance of Pacific white shrimp (Litopenaeus vannamei) juveniles were studied. Four experimental
Sang Woon Chung et al.
Journal of medicinal food, 12(2), 345-350 (2009-05-23)
Peroxisome proliferator-activated receptors (PPARs), members of the nuclear hormone receptor family, are key regulators of various metabolic pathways related to lipid and glucose metabolism as well as inflammation. We examined the effect of zingerone, a major ingredient of ginger, on
Mark A Affeltranger et al.
Chemical senses, 32(5), 455-462 (2007-04-03)
Sequential presentation of 2 irritants may produce cross-sensitization or cross-adaptation effects upon introduction of the second irritant. In Experiment 1, subjects were given either 34 min of stimulation with zingerone, capsaicin, or piperine or one of those irritants for 23
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