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Acetovanillone

Acetovanillone structure

CAS No:
498-02-2
Formula:
C9H10O3
Chemical Name:
Acetovanillone
Synonyms:
Ethanone,1-(4-hydroxy-3-methoxyphenyl)-;Acetophenone,4′-hydroxy-3′-methoxy-;1-(4-Hydroxy-3-methoxyphenyl)ethanone;Acetoguaiacone;Acetovanillone;Apocynin;Apocynine;4-Acetyl-2-methoxyphenol;3′-Methoxy-4′-hydroxyacetophenone;4′-Hydroxy-3′-methoxyacetophenone;Acetoguaiacon;4-Hydroxy-3-methoxyphenyl methyl ketone;2-Methoxy-4-acetylphenol;4-Acetylguaiacol;Acetoguaicone;NSC 209524;NSC 2146;3-Methoxy-4-hydroxyphenylethanone;Acetoguaiacol;1-(4-Hydroxy-3-methoxyphenyl)ethan-1-one;4-Acetyl-1-hydroxy-2-methoxybenzene
Categories:
Pharmaceutical Intermediates > Antipsychotics

Description

Apocynin is a selective NADPH-oxidase inhibitor with an IC50 of 10 μM.

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.|Acetovanillone has been used in trials studying the treatment of Bronchial Asthma and Chronic Obstructive Pulmonary Disease.

Acetovanillone Basic Attributes

Molecular Weight：

166.17

Exact Mass：

166.17

BRN：

637373

EC Number：

207-854-5

UNII：

B6J7B9UDTR

NSC Number：

209524|2146

DSSTox ID：

DTXSID7060097

HScode：

29145000

Characteristics

PSA：

46.5

XLogP3：

0.5

Appearance：

Yellow to brown Solid

Density：

1.2±0.1 g/cm3

Melting Point：

115 °C

Boiling Point：

297 °C

Flash Point：

>230 °F

Refractive Index：

1.538

Water Solubility：

soluble in hot water

Storage Conditions：

Refrigerator

Vapor Pressure：

0.000759mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

RTECS Number：

AM8800000

Marks：

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

Drug Information

MeSH：

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

MeSH Entry Terms：

4'-hydroxy-3'-methoxyacetophenone

Acetovanillone Use and Manufacturing

Uses

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

Manufacturing Info：

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

Use Classification：

Food additives -> Flavoring Agents

Food Additive Classes：

Flavoring Agents

Computed Properties

Molecular Weight:166.17
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:166.062994177
Monoisotopic Mass:166.062994177
Topological Polar Surface Area:46.5
Heavy Atom Count:12
Complexity:167
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

Acetylacetone

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