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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:
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

Quality Level

400

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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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS2627
SHBQ8776
SHBR2004
SHBP2334
SHBP0806

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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)
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)
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)
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