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W508454

Sigma-Aldrich

Acetovanillone

≥98%, FG

Synonym(s):

4′-Hydroxy-3′-methoxyacetophenone, Acetovanillone, Apocynin

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About This Item

Linear Formula:
HOC6H3(OCH3)COCH3
CAS Number:
498-02-2
Molecular Weight:
166.17
Beilstein/REAXYS Number:
637373
EC Number:
207-854-5
MDL number:
MFCD00008747
UNSPSC Code:
12164502
PubChem Substance ID:
24902039
Flavis number:
7.142
NACRES:
NA.21

biological source

synthetic

grade

FG
Fragrance grade
Halal

agency

follows IFRA guidelines

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 872/2012
FDA 21 CFR 110

assay

≥98%

bp

263-265 °C/17 mmHg (lit.)

mp

112-115 °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

vanilla

SMILES string

COc1cc(ccc1O)C(C)=O

InChI

1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3

InChI key

DFYRUELUNQRZTB-UHFFFAOYSA-N

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Related Categories

General description

Acetovanillone is a structural analog of vanillin that occurs mainly in wine aged in oak barrels. It is a potent NADPH oxidase inhibitor.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Volatile composition of aged wine in used barrels of French oak and of American oak.
Cerdan TG, et al.
Food Research International, 35(7), 603-610 (2002)
Elham Khanicheh et al.
Arteriosclerosis, thrombosis, and vascular biology, 33(9), 2187-2192 (2013-08-03)
Antioxidative drugs continue to be developed for the treatment of atherosclerosis. Apocynin is an nicotinamide adenine dinucleotide phosphate oxidase inhibitor with anti-inflammatory properties. We used contrast-enhanced ultrasound molecular imaging to assess whether short-term apocynin therapy in atherosclerosis reduces vascular oxidative
Jingfei Zhang et al.
Neuron, 82(1), 195-207 (2014-03-19)
Complement receptor 3 (CR3) activation in microglia is involved in neuroinflammation-related brain disorders and pruning of neuronal synapses. Hypoxia, often observed together with neuroinflammation in brain trauma, stroke, and neurodegenerative diseases, is thought to exacerbate inflammatory responses and synergistically enhance brain
The NADPH oxidase inhibitor apocynin (acetovanillone) induces oxidative stress.
Riganti C, et al.
Toxicology and Applied Pharmacology, 212(3), 179-187 (2006)
Determination of volatile oak compounds in wine by headspace solid-phase microextraction and gas chromatography?mass spectrometry.
Carrillo JD, et al.
Journal of Chromatography A, 1102(1), 25-36 (2006)
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