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Acetovanillone

Acetovanillone structure

CAS No.: 498-02-2

Chemical Name:: Acetovanillone

Synonyms: APOCYNIN;4-HYDROXY-3-METHOXYACETOPHENONE;1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE;Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-;Acetovanilone;ACETOVANILLON;Apocynin (Acetovanillone);4'-HYDROXY-3'-METHOXYACETOPHENONE;Apocynin - CAS 498-02-2 - Calbiochem;NSC 2146

CBNumber:: CB7484931

Molecular Formula:: C9H10O3

Molecular Weight:: 166.17

MDL Number:: MFCD00008747

MOL File:: 498-02-2.mol

MSDS File:: SDS

Last updated:2024-11-19 23:02:33

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Acetovanillone Properties

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)
EWG's Food Scores	1
FDA UNII	B6J7B9UDTR
NIST Chemistry Reference	Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-(498-02-2)
EPA Substance Registry System	Acetovanillone (498-02-2)

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS07

Signal word

Warning

Hazard statements

H315-H319-H335

Precautionary statements

P261-P264-P271-P280-P302+P352-P305+P351+P338

Hazard Codes

Risk Statements

36/37/38

Safety Statements

26-36

WGK Germany

RTECS

AM8800000

TSCA

Yes

HS Code

29145000

NFPA 704

	1
2		0

Acetovanillone price More Price(61)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	A10809	4′-Hydroxy-3′-methoxyacetophenone 98%	498-02-2	25g	$41.6	2024-03-01	Buy
Sigma-Aldrich	178385	Apocynin - CAS 498-02-2 - Calbiochem A cell-permeable, anti-inflammatory phenolic compound that acts as a potent and selective inhibitor of NADPH oxidase.	498-02-2	1g	$96.7	2024-03-01	Buy
Sigma-Aldrich	73536	Acetovanillone analytical standard	498-02-2	100mg	$62.8	2022-05-15	Buy
TCI Chemical	H0261	4'-Hydroxy-3'-methoxyacetophenone >98.0%(GC)	498-02-2	25g	$69	2024-03-01	Buy
TCI Chemical	H0261	4'-Hydroxy-3'-methoxyacetophenone >98.0%(GC)	498-02-2	100g	$207	2024-03-01	Buy

Product number	Packaging	Price	Buy
A10809	25g	$41.6	Buy
178385	1g	$96.7	Buy
73536	100mg	$62.8	Buy
H0261	25g	$69	Buy
H0261	100g	$207	Buy

Acetovanillone Chemical Properties,Uses,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

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.

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.

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

3,4-Dihydroxyacetophenone 2-METHOXYPHENYL ACETATE Zinc chloride

Preparation Products

Acetylacetone 4-Hydroxy-3-methoxystyrene METHOXYBENZOQUINONE 4-chloro-6,7-dimethoxyquinoline 1-(2-hydroxy-3-methoxy-phenyl)ethanone

1-(4,5-DIMETHOXY-2-NITRO-PHENYL)-ETHANONE 4-Ethylresorcinol 4-METHOXY-3-HYDROXYACETOPHENONE 2,4-Dimethoxyacetophenone Quinoline, 4-chloro-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-

4-(4-Acetyl-2-Methoxyphenoxy)-butanoic Acid Ethyl Ester 2-bromo-1-(4-hydroxy-3-methoxyphenyl)ethanone

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Acetovanillone Suppliers

Global( 517)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Hebei Mojin Biotechnology Co., Ltd	+86 13288715578 +8613288715578	sales@hbmojin.com	China	12840	58
Hubei Langyou International Trading Co., Ltd	+86-18874586545 +86-18874586545	linda@xrdchem.cn	China	196	58
Hebei Chuanghai Biotechnology Co,.LTD	+86-13131129325	sales1@chuanghaibio.com	China	5893	58
Henan Fengda Chemical Co., Ltd	+86-371-86557731 +86-13613820652	info@fdachem.com	China	20287	58
Shaanxi TNJONE Pharmaceutical Co., Ltd	+8618092446649	sarah@tnjone.com	China	1143	58
Capot Chemical Co.,Ltd.	+86-（0）57185586718 +86-13336195806	sales@capot.com	China	29791	60
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21634	55
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	32957	60
Anqing Chico Pharmaceutical Co., Ltd.	15380796838	chloewu@chicopharm.cn	CHINA	340	58
Shanghai Zheyan Biotech Co., Ltd.	18017610038	zheyansh@163.com	CHINA	3619	58

Supplier	Advantage
Hebei Mojin Biotechnology Co., Ltd	58
Hubei Langyou International Trading Co., Ltd	58
Hebei Chuanghai Biotechnology Co,.LTD	58
Henan Fengda Chemical Co., Ltd	58
Shaanxi TNJONE Pharmaceutical Co., Ltd	58
Capot Chemical Co.,Ltd.	60
Henan Tianfu Chemical Co.,Ltd.	55
ATK CHEMICAL COMPANY LIMITED	60
Anqing Chico Pharmaceutical Co., Ltd.	58
Shanghai Zheyan Biotech Co., Ltd.	58

View Lastest Price from Acetovanillone manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-11-19	Apocynin 498-02-2	US $50.00 / mL		99.98%	10g	TargetMol Chemicals Inc.
2024-10-11	Acetovanillone 498-02-2	US $5.00-2.00 / KG	1KG	99%	10000kg	Hebei Chuanghai Biotechnology Co,.LTD
2024-04-20	3-Methoxy-4-hydroxyacetophenone 498-02-2	US $600.00 / Kg	1Kg	98	500 Kg	R&D Scientific Inc.

Apocynin
498-02-2
US $50.00 / mL
99.98%
TargetMol Chemicals Inc.

Acetovanillone
498-02-2
US $5.00-2.00 / KG
99%
Hebei Chuanghai Biotechnology Co,.LTD

3-Methoxy-4-hydroxyacetophenone
498-02-2
US $600.00 / Kg
98
R&D Scientific Inc.

Acetovanillone Spectrum

Acetovanillone(498-02-2)MS Acetovanillone(498-02-2)¹HNMR Acetovanillone(498-02-2)¹³CNMR Acetovanillone(498-02-2)IR1 Acetovanillone(498-02-2)IR2 Acetovanillone(498-02-2)Raman

498-02-2(Acetovanillone)Related 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

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