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Merck
CN

73536

Acetovanillone

analytical standard

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
EC Number:
207-854-5
UNSPSC Code:
85151701
PubChem Substance ID:
329764935
Beilstein/REAXYS Number:
637373
MDL number:
MFCD00008747

Key Documents

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InChI key

DFYRUELUNQRZTB-UHFFFAOYSA-N

InChI

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

SMILES string

COc1cc(ccc1O)C(C)=O

grade

analytical standard

assay

≥98.0% (GC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

bp

263-265 °C/17 mmHg (lit.)

Quality Level

100

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

format

neat

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General description

Acetovanillone is an aromatic plant ketone, which is a selective inhibitor of NADPH oxidase. It is mainly secreted in the urine of mammals as the corresponding glucuronide conjugate.

Application

Acetovanillone may be used as a reference standard for the determination of the analyte in Vanilla planifolia using reversed-phase high-performance liquid chromatography (RP-HPLC).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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

WGK 2

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH5537
BCCB4012
BCBV7372

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Handbook of Mammalian Metabolism of Plant Compounds (1991) (2017)
Development and validation of an RP?HPLC method for quantitative determination of vanillin and related phenolic compounds in Vanilla planifolia.
Sinha KA, et al.
Journal of Separation Science, 30(1), 15-20 (2007)
The NADPH oxidase inhibitor apocynin (acetovanillone) induces oxidative stress.
Riganti C, et al.
Toxicology and Applied Pharmacology, 212(3), 179-187 (2006)
Hye Kyoung Sung et al.
Scientific reports, 9(1), 4668-4668 (2019-03-16)
Iron overload is associated with various pathological changes which contribute to heart failure. Here, we examined mechanisms via which iron alters cardiomyocyte insulin sensitivity. Treatment of primary adult and neonatal cardiomyocytes as well as H9c2 cells with iron decreased insulin

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