Acetovanillone

ChemicalBook > CAS DataBase List > Acetovanillone

Product Name: Acetovanillone
CAS No.: 498-02-2
Chemical Name: Acetovanillone
Synonyms: APOCYNIN;4-HYDROXY-3-METHOXYACETOPHENONE;Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-;1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE;Acetovanilone;ACETOVANILLON;Apocynin (Acetovanillone);4'-HYDROXY-3'-METHOXYACETOPHENONE;Apocynin - CAS 498-02-2 - Calbiochem;NSC 2146
CBNumber: CB7484931
Molecular Formula: C9H10O3
Formula Weight: 166.17
MOL File: 498-02-2.mol

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Acetovanillone Property

Melting point:: 112-115 °C (lit.)
Boiling point:: 263-265 °C/17 mmHg (lit.)
Density: 1.1708 (rough estimate)
refractive index: 1.5101 (estimate)
Flash point:: >230 °F
storage temp.: Sealed in dry,Room Temperature
solubility: Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methan
pka: 8.18±0.18(Predicted)
form: Solid
color: Yellow to brown
Odor: at 100.00 %. faint sweet vanillin
Odor Type: vanilla
Water Solubility: soluble in hot water
Merck: 14,741
BRN: 637373
LogP: 1.389 (est)
CAS DataBase Reference: 498-02-2(CAS DataBase Reference)
NIST Chemistry Reference: Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-(498-02-2)
EPA Substance Registry System: Acetovanillone (498-02-2)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 2
RTECS: AM8800000
TSCA: Yes
HS Code: 29145000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: A10809
Product name: 4′-Hydroxy-3′-methoxyacetophenone
Purity: 98%
Packaging: 25g
Price: $41.6
Updated: 2024/03/01

Sigma-Aldrich

Product number: 178385
Product name: Apocynin - CAS 498-02-2 - Calbiochem
Purity: A cell-permeable, anti-inflammatory phenolic compound that acts as a potent and selective inhibitor of NADPH oxidase.
Packaging: 1g
Price: $96.7
Updated: 2024/03/01

Sigma-Aldrich

Product number: 73536
Product name: Acetovanillone
Purity: analytical standard
Packaging: 100mg
Price: $62.8
Updated: 2022/05/15

TCI Chemical

Product number: H0261
Product name: 4'-Hydroxy-3'-methoxyacetophenone
Purity: >98.0%(GC)
Packaging: 25g
Price: $69
Updated: 2024/03/01

TCI Chemical

Product number: H0261
Product name: 4'-Hydroxy-3'-methoxyacetophenone
Purity: >98.0%(GC)
Packaging: 100g
Price: $207
Updated: 2024/03/01

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Acetovanillone Chemical Properties,Usage,Production

Chemical Properties

Acetovanillone is a yellowish to brown powder, soluble in alcohol, essential oils, and perfume chemicals. It is slightly soluble in water at room temperature but readily dissolves in hot water. It has a very faint, sweet odor, faintly reminiscent of vanillin, but with less spiciness and somewhat fresher notes. It occurs widely in nature, including in Orris root distillate.

Uses

4'-Hydroxy-3'-methoxyacetophenone is used as an inhibitor of nicotinamide adenine dinucleotide phosphate (NADPH) oxidase, which is an enzyme responsible for reactive oxygen species production. It is also useful in the treatment of various inflammatory diseases and atherosclerosis. Further, it shows an anti-inflammatory activity and improves endothelial function by reducing oxidative stress. In addition to this, it is used for studying nitric oxide regulated processes in plants.

Uses

Acetovanillone is an inhibitor of NADPH oxidase (an enzyme responsible for reactive oxygen species production) and is useful in the treatment of various inflammatory diseases.

Definition

ChEBI: Apocynin is an aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an antirheumatic drug, a peripheral nervous system drug, an EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor and a plant metabolite. It is a member of acetophenones, a methyl ketone and an aromatic ketone.

Preparation

Synthetically by methylation of 3,4-Dihydroxyacetophenone. It can also be obtained by Fries rearrangement of guaiacol acetate in the presence of zinc chloride. It can be isolated from the extract of the roots of Indian hemp, Apocynum cannabinum L.

Production Methods

Synthetically by methylation of 3,4- Dihydroxy acetophenone. Also from Guaiacol acetate with Zinc chloride and Acetic anhydride. Can be isolated from the extract of the roots of Indian hemp, Apocynum cannabinum L.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 739, 1995 DOI: 10.1021/jo00108a046

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.

storage

Store at RT

Purification Methods

Crystallise apocynin from water, or EtOH/pet ether. [Beilstein 8 IV 1814.]

References

[1] GARA N DEXTER. Bacterial catabolism of acetovanillone, a lignin-derived compound.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2022: e2213450119. DOI:10.1073/pnas.2213450119.
[2] YUDAI HIGUCHI. The Catabolic System of Acetovanillone and Acetosyringone in Sphingobium sp. Strain SYK-6 Useful for Upgrading Aromatic Compounds Obtained through Chemical Lignin Depolymerization.[J]. Applied and Environmental Microbiology, 2022, 88 16: e0072422. DOI:10.1128/aem.00724-22.
[3] CHIARA RIGANTI. The NADPH oxidase inhibitor apocynin (acetovanillone) induces oxidative stress[J]. Toxicology and applied pharmacology, 2006, 212 3: Pages 179-187. DOI:10.1016/j.taap.2005.07.011.
[4] GJERTSEN FB Scheline R Solheim E. Metabolism of aromatic plant ketones in rats: Acetovanillone and paeonol[J]. Journal of ethnopharmacology, 1988, 23 2: Page 342. DOI:10.1016/0378-8741(88)90035-9.

Acetovanillone Preparation Products And Raw materials

Raw materials

Preparation Products

Acetylacetone

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View Lastest Price from Acetovanillone manufacturers

Hebei Chuanghai Biotechnology Co,.LTD

Product: Acetovanillone 498-02-2
Price: US $5.00-2.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 10000kg
Release date: 2024-08-20

Hebei Weibang Biotechnology Co., Ltd

Product: Acetovanillone 498-02-2
Price: US $10.00/PCS
Min. Order: 1KG
Purity: 99%
Supply Ability: 10 mt
Release date: 2021-04-02

R&D Scientific Inc.

Product: 3-Methoxy-4-hydroxyacetophenone 498-02-2
Price: US $600.00/Kg
Min. Order: 1Kg
Purity: 98
Supply Ability: 500 Kg
Release date: 2024-04-19

498-02-2, AcetovanilloneRelated Search:

2'-Methoxyacetophenone 2'-Hydroxyacetophenone 4'-Bromoacetophenone 2',4'-Dichloroacetophenone 3'-Methylacetophenone 3-Nitroacetophenone 4-Nitroacetophenone 3',5'-Dimethoxyacetophenone 3-Methoxyacetophenone CHLOROPHOSPHONAZO III Acetophenone 2-HYDROXYACETOPHENONE 4'-Methoxyacetophenone 3-Aminoacetophenone 3,4-Dimethoxyacetophenone 4'-Hydroxyacetophenone Calcium lactate 3,4-Methylenedioxyacetophenone

Apocynin - CAS 498-02-2 - Calbiochem

1-(4-hydroxy-3-methoxyphenyl)-ethanon

1-(4-Hydroxy-3-methoxyphenyl)-ethanone (acetovanillone)

1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE

1-(4-HYDROXY-3-METHOXYPHENYL) ETHANONE

Acetovanillone~Apocynin

4'-Hydroxy-3'-Methoxyacetophenone 3-Methoxy-4-Hydroxyacetophenone 3'-Methoxy-4'-Hydroxyacetophenone

ACETOVANILLONE 98+%

acetovanillone,1-(4-hydroxy-3-methoxyphenyl)-ethanone,apocynin

Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-

ACETAVANILLONE

Ethanone,1-(4-hydroxy-3-me

ETHANONE,1-(4-HYDROXY-3-METHO

Acetovanillone, 98% 100GR

ACETOVANILLONE (4-HYDROXY-3-METHOXYACETOPHENONE)

4'-hydroxy-3'-methoxyacetophenone,1-(4-hydroxy-3-methoxy)ethanone

4-Acetylguaiacol

Acetovanillone ,99%

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

1-(4-Hydroxy-3-methoxyphenyl)ethan-1-one, Acetovanillone

AcetovaniL

4’-hydroxy-3’-methoxy-acetophenon

4-Acetyl-2-methoxyphenol

4-Hydroxy-3-methoxyphenyl methyl ketone

Acetoguaiacon

Acetoguaiacone

Acetophenone, 4'-hydroxy-3'-methoxy-

Acetovanilone

Acetovanyllon

-Acetylguaiacol

Apocynine

-Hydroxy-3-methoxyphenyl methyl keton

-Methoxy-4-acetylphenol

'-Methoxy-4'-hydroxyacetophenone

Phenol, 4-acetyl-2-methoxy

3-Metoksy-4-hydroksyacetofenon

TIMTEC-BB SBB008060

APOCYNIN

AURORA KA-3667

ACETOVANILLON

ACETOVANILLONE

AKOS BBS-00003229

3'-METHOXY-4'-HYDROXYACETOPHENONE

3-METHOXY-4-HYDROXYACETOPHENONE

4'-HYDROXY-3'-METHOXYACETOPHENONE

4-HYDROXY-3-METHOXYACETOPHENONE

NSC 209524

NSC 2146

Acetovanillon/ Apocynin

2-Methoxy-4-acetylphenol

Acetoguaicone

Apocynin (Acetovanillone)

Apocynin, >=98%

Vanilloyl methyl keton

Acetovanillone, 98.5%

4-Hydroxy 3-Methoxy Acetophenone (Acetovanillone)

Acetovanillone, 98.5%, for synthesis

4'-Hydroxy-3'-methoxyacetophenone&gt