ChemicalBook > CAS DataBase List > 4-METHOXY-3-HYDROXYACETOPHENONE

4-METHOXY-3-HYDROXYACETOPHENONE

Product Name
4-METHOXY-3-HYDROXYACETOPHENONE
CAS No.
6100-74-9
Chemical Name
4-METHOXY-3-HYDROXYACETOPHENONE
Synonyms
1-(3-hydroxy-4-Methoxyphenyl)ethan-1-one;Acetoisovanillone;Ethanone, 1-(3-hydroxy-4-Methoxyphenyl)-;3-HYDROXY-4-METHOXYACETOPHENONE;Isoacetovanillone;NSC 30050;ACETOISOVANILLONE(SH);Diosmin EP Impurity A;Dioxamine EP Impurity A;5-Acetyl-2-methoxyphenol
CBNumber
CB3435814
Molecular Formula
C9H10O3
Formula Weight
166.17
MOL File
6100-74-9.mol
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4-METHOXY-3-HYDROXYACETOPHENONE Property

Melting point:
88-92 °C
Boiling point:
329.9±27.0 °C(Predicted)
Density 
1.158
storage temp. 
Inert atmosphere,Room Temperature
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Solid
pka
9.15±0.10(Predicted)
color 
Off-White to Yellow
Stability:
Stable. Incompatible with strong oxidizing agents.
InChI
InChI=1S/C9H10O3/c1-6(10)7-3-4-9(12-2)8(11)5-7/h3-5,11H,1-2H3
InChIKey
YLTGFGDODHXMFB-UHFFFAOYSA-N
SMILES
C(=O)(C1=CC=C(OC)C(O)=C1)C
LogP
1.373 (est)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
HS Code 
2914390090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

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

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
679704
Product name
3′-Hydroxy-4′-methoxyacetophenone
Purity
97%
Packaging
1g
Price
$100
Updated
2025/07/31
Sigma-Aldrich
Product number
679704
Product name
3′-Hydroxy-4′-methoxyacetophenone
Purity
97%
Packaging
5g
Price
$193
Updated
2025/07/31
TRC
Product number
I780000
Product name
Isoacetovanillone
Packaging
50g
Price
$545
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
59229
Product name
Isoacetovanillone
Packaging
2.5g
Price
$610
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CHM0079203
Product name
4-METHOXY-3-HYDROXYACETOPHENONE
Purity
95.00%
Packaging
1G
Price
$642.18
Updated
2021/12/16
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4-METHOXY-3-HYDROXYACETOPHENONE Chemical Properties,Usage,Production

Chemical Properties

solid

Uses

Isoacetovanillone (Diosmin EP Impurity A) is a volatile compound isolated from oak wood. Also a byproduct in the production of Acetovanillone.

Uses

Isoacetovanillone is a volatile compound isolated from oak wood. Also a byproduct in the production of Acetovanillone.

Definition

ChEBI: Isoacetovanillone is a member of phenols and a member of methoxybenzenes. It has a role as a metabolite.

Preparation

Preparation by saponification of 3-acetoxy-4-methoxy-acetophenone (90%) (59%).

Synthesis Reference(s)

Synthetic Communications, 18, p. 1379, 1988 DOI: 10.1080/00397918808078806

Synthesis

88114-44-7

6100-74-9

General procedure for the synthesis of 4-methoxy-3-hydroxyacetophenone from 3'-hydroxy-4'-methoxyacetophenone (12): ketone 8 (250 mg, 1.20 mmol) was dissolved in anhydrous CH2Cl2 (3 mL), AlCl3 (208 mg, 1.56 mmol) was added, and the reaction was stirred for 24 h at 18 °C and under nitrogen protection. After completion of the reaction, the mixture was partitioned between water (10 mL) and CH2Cl2 (10 mL). The aqueous phase was extracted once with CH2Cl2 (10 mL), the organic phases were combined, dried with MgSO4, filtered and concentrated under reduced pressure. The light yellow oil obtained was purified by fast chromatography (eluent: ethyl acetate/hexane, 1:4 v/v) to give a white solid 4-methoxy-3-hydroxyacetophenone 124 (172 mg, 86% yield) with a melting point of 88.6-90.5 °C (literature value: 92-93 °C) and a TLC (silica gel plate, unfolding agent: ethyl acetate/hexane, 1:1 v/v) Rf value was 0.4. 1H NMR (300MHz, CDCl3) δ: 7.53-7.56 (m, 2H), 6.89 (d, J=7.5Hz, 1H), 5.73 (br s, 1H), 3.96 (s, 3H), 2.54 (s, 3H).

References

[1] Patent: WO2008/124878, 2008, A1. Location in patent: Page/Page column 38

4-METHOXY-3-HYDROXYACETOPHENONE Preparation Products And Raw materials

Raw materials

Preparation Products

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4-METHOXY-3-HYDROXYACETOPHENONE Suppliers

Canada 1 China 142 Europe 2 India 7 Switzerland 1 Ukraine 1 United Kingdom 5 United States 23 USA 1 Global 183
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View Lastest Price from 4-METHOXY-3-HYDROXYACETOPHENONE manufacturers

Hebei Chuanghai Biotechnology Co,.LTD
Product
4-METHOXY-3-HYDROXYACETOPHENONE 6100-74-9
Price
US $10.70/KG
Min. Order
10KG
Purity
99%
Supply Ability
10000kg
Release date
2024-08-20
Shanghai Standard Technology Co., Ltd.
Product
4-Methoxy-3-Hydroxyacetophenone 6100-74-9
Price
US $0.00/mg
Min. Order
100mg
Purity
≥98%(HPLC)
Supply Ability
100 g
Release date
2020-06-01
Career Henan Chemical Co
Product
4-METHOXY-3-HYDROXYACETOPHENONE CC
Price
US $1.00/KG
Min. Order
1 mg
Purity
99%
Supply Ability
100KG
Release date
2018-12-25

6100-74-9, 4-METHOXY-3-HYDROXYACETOPHENONERelated Search:

3,4-Methylenedioxyacetophenone 3′,4′-(Methylenedioxy)propiophenone 5,6-Dimethoxy-1-indanone 3',5-DIHYDROXY-4',6,7-TRIMETHOXYFLAVONE 2,3,3',4'-TETRAMETHOXYBENZOPHENONE 3,7,3',4'-TETRAMETHYLGOSSYPETIN 2'-AMINO-4',5'-DIMETHOXYACETOPHENONE EUPATORIN-5-METHYL ETHER 2',3',4'-TRIMETHOXYACETOPHENONE 3',4',5'-TRIMETHOXYACETOPHENONE 3,4-Dimethoxyacetophenone 4',6,7-Trimethoxyisoflavone 6-Acetyl-1,4-benzodioxane 4'-METHOXY-2'-HYDROXYACETOPHENONE,4-METHOXY-2-HYDROXYACETOPHENONE,Methoxy-2-hydroxyAcetophenone 5-Methoxy-2-hydroxyacetophenone Acetovanillone 6,7-DIMETHOXY-2,2-DIMETHYL-4-CHLOROMANONE Santalin

  • Acetoisovanillone
  • 1-(3-hydroxy-4-Methoxyphenyl)ethan-1-one
  • Ethanone, 1-(3-hydroxy-4-Methoxyphenyl)-
  • 5-Acetyl-2-methoxyphenol
  • Isoacetovanillone
  • NSC 30050
  • ACETOISOVANILLONE(SH)
  • 3-HYDROXY-4-METHOXYACETOPHENONE
  • 4'-METHOXY-3'-HYDROXYACETOPHENONE
  • 4-METHOXY-3-HYDROXYACETOPHENONE
  • 1-(3-hydroxy-4-methoxy-phenyl)ethanone
  • Diosmin EP Impurity A
  • Diosmin Impurity 1 (Diosmin EP Impurity A)
  • 3'-Hydroxy-4'-methoxyacetophenone 97%
  • Isoacetovanillone (1.0 mg/mL in Methanol)
  • -METHOXY-3-HYDROXYACETOPHENONE
  • 1-(3-hydroxy-4-methoxyphenyl)ethan-1-one (acetoisovanillone),
  • 3'-Hydroxy-4'-methoxyacetophenone
  • Dioxamine EP Impurity A
  • 6100-74-9
  • Building Blocks
  • C9
  • Carbonyl Compounds
  • Organic Building Blocks
  • Ketones
  • Aromatic Acetophenones & Derivatives (substituted)