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498-02-2

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498-02-2 Usage

Chemical Properties

yellowish to brown powder

Uses

Different sources of media describe the Uses of 498-02-2 differently. You can refer to the following data:
1. 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.
2. 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.

Preparation

Also obtained by Fries rearrangement of guaiacol acetate in the presence of zinc chloride.

Definition

ChEBI: An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.

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.

Purification Methods

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

Check Digit Verification of cas no

The CAS Registry Mumber 498-02-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 8 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 498-02:
(5*4)+(4*9)+(3*8)+(2*0)+(1*2)=82
82 % 10 = 2
So 498-02-2 is a valid CAS Registry Number.

498-02-2 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (H0261)  4'-Hydroxy-3'-methoxyacetophenone  >98.0%(GC)

  • 498-02-2

  • 25g

  • 180.00CNY

  • Detail
  • TCI America

  • (H0261)  4'-Hydroxy-3'-methoxyacetophenone  >98.0%(GC)

  • 498-02-2

  • 100g

  • 510.00CNY

  • Detail
  • TCI America

  • (H0261)  4'-Hydroxy-3'-methoxyacetophenone  >98.0%(GC)

  • 498-02-2

  • 500g

  • 1,500.00CNY

  • Detail
  • Alfa Aesar

  • (A10439)  4'-Hydroxy-3'-methoxyacetophenone, 98%   

  • 498-02-2

  • 50g

  • 211.0CNY

  • Detail
  • Alfa Aesar

  • (A10439)  4'-Hydroxy-3'-methoxyacetophenone, 98%   

  • 498-02-2

  • 250g

  • 757.0CNY

  • Detail
  • Alfa Aesar

  • (A10439)  4'-Hydroxy-3'-methoxyacetophenone, 98%   

  • 498-02-2

  • 500g

  • 1229.0CNY

  • Detail

498-02-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name apocynin

1.2 Other means of identification

Product number -
Other names 1-(4-hydroxy-3-methoxyphenyl)ethanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:498-02-2 SDS

498-02-2Synthetic route

3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

4CH3(1-)*Zn(2+)*Li(1+)

4CH3(1-)*Zn(2+)*Li(1+)

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: 3-methoxy-4-hydroxybenzoic acid; 4CH3(1-)*Zn(2+)*Li(1+) In tetrahydrofuran; diethyl ether; hexane at 20℃; Schlenk technique; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran; diethyl ether; hexane at 20℃; Solvent; Schlenk technique; Inert atmosphere; chemoselective reaction;
96%
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol
7382-68-5

1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 14h;A n/a
B 96%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere;A 86%
B 82%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; Green chemistry;A 86%
B 82%
With C22H17Cl3N3ORh; sodium hydroxide In water for 60h; Inert atmosphere;
2-methoxyphenyl acetate
613-70-7

2-methoxyphenyl acetate

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With aluminum (III) chloride In nitrobenzene at 40℃; for 3h; Reagent/catalyst; Temperature; Large scale;90.23%
With methanesulfonic acid In dichloromethane under 15751.6 Torr; Reagent/catalyst; Fries Phenol Ester Rearrangement; Flow reactor;75%
With methanesulfonic acid; phosphorus pentoxide at 90℃; for 5h; Fries rearrangement;67%
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one
22317-35-7

1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;A 84%
B 78%
With RuH2(CO)(PPh3)3; hydrogen; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In (2)H8-toluene at 135℃; under 760.051 Torr; for 20h;
1-(3,4-dihydroxyphenyl)ethan-1-one
1197-09-7

1-(3,4-dihydroxyphenyl)ethan-1-one

methyl iodide
74-88-4

methyl iodide

A

3-hydroxy-4-methoxyacetophenone
6100-74-9

3-hydroxy-4-methoxyacetophenone

B

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

C

1-(3,4-dimethoxyphenyl)ethanone
1131-62-0

1-(3,4-dimethoxyphenyl)ethanone

Conditions
ConditionsYield
With lithium carbonate In N,N-dimethyl-formamide at 55℃; for 18h; Inert atmosphere; chemoselective reaction;A 84%
B 6%
C 4%
C29H37NO8

C29H37NO8

A

methyl 3,4-dimethoxybenzoate
2150-38-1

methyl 3,4-dimethoxybenzoate

B

C19H18O7

C19H18O7

C

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With sulfuric acid In methanol at 80℃; for 1h;A 80%
B 5%
C 83%
1,2-dimethoxybenzene
91-16-7

1,2-dimethoxybenzene

acetyl chloride
75-36-5

acetyl chloride

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With ytterbium(III) triflate In carbon disulfide for 6h; Friedel-Crafts reaction; Heating;79%
C18H30O3Si
1445875-26-2

C18H30O3Si

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With water; acetic acid; N,N,N',N'-tetramethylguanidine In tetrahydrofuran; acetonitrile at 20℃;75%
With acetic acid In tetrahydrofuran; water; acetonitrile at 20℃; for 12h; pH=7.5;63%
4-hydroxy-3-methoxybenzoylacetic acid
84272-48-0

4-hydroxy-3-methoxybenzoylacetic acid

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With sulfuric acid Heating;66%
4'-tert-butyldimethylsilyloxy-3'-methoxyacetophenone
132255-78-8

4'-tert-butyldimethylsilyloxy-3'-methoxyacetophenone

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran; water; acetonitrile at 20℃; for 12h; pH=7.5;63%
With water; acetic acid; N,N,N',N'-tetramethylguanidine In tetrahydrofuran; acetonitrile at 20℃;63%
sodium acetate
127-09-3

sodium acetate

2-methoxy-phenol
90-05-1

2-methoxy-phenol

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With poly phosphoric acid (PPA) at 100℃; for 0.333333h; Time;44.2%
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol
7382-68-5

1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol

A

Apocynol
2480-86-6

Apocynol

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

C

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

D

phenol
108-95-2

phenol

Conditions
ConditionsYield
With sodium hydroxide; nickel at 25℃; Product distribution; Further Variations:; Temperatures; other substrates, other current densities; Catalytic hydrogenation; Electrochemical reaction;A 41%
B 43%
C 1.3%
D 2%
1-(3,4-dimethoxyphenyl)-2-(4-(1-hydroxyethyl)-2-methoxyphenoxy)propane-1,3-diol

1-(3,4-dimethoxyphenyl)-2-(4-(1-hydroxyethyl)-2-methoxyphenoxy)propane-1,3-diol

A

2-(4-acetyl-2-methoxyphenoxy)-1-(3,4-dimethoxyphenyl)propane-1,3-diol

2-(4-acetyl-2-methoxyphenoxy)-1-(3,4-dimethoxyphenyl)propane-1,3-diol

B

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

C

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(l) chloride In acetonitrile at 25℃; under 735.576 Torr; for 20h; chemoselective reaction;A 35%
B 12%
C 9%
2-(2,6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)ethan-1-one
906668-05-1

2-(2,6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

A

1,3-dimethoxy-2-hydroxy-benzene
91-10-1

1,3-dimethoxy-2-hydroxy-benzene

B

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With lithium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 2.5h; Electrolysis;A 28%
B 22%
Apocynol
2480-86-6

Apocynol

A

2-methoxy-1,4-benzoquinone
2880-58-2

2-methoxy-1,4-benzoquinone

B

vanillin
121-33-5

vanillin

C

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile for 0.5h; Microwave irradiation;A 23%
B 5%
C 18%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

A

4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

B

vanillin
121-33-5

vanillin

C

4-hydroxy-3-methoxybenzoylacetic acid
84272-48-0

4-hydroxy-3-methoxybenzoylacetic acid

D

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With salcomine; oxygen In methanol at 25℃; under 7600 Torr; for 72h;A 20%
B 16%
C n/a
D n/a
With salcomine; oxygen In methanol at 25℃; under 7600 Torr; for 72h; Product distribution; also with following CH2N2/ether action, other products;A 20%
B 16%
C n/a
D n/a
alkaline lignin

alkaline lignin

A

vanillin
121-33-5

vanillin

B

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With prolinium tetrachloromanganate(II); ethylammonium nitrate (EAN) at 35℃; for 4h; Time;A 20%
B n/a
Apocynol
2480-86-6

Apocynol

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile for 0.5h; Reagent/catalyst; Microwave irradiation;18%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 4h;
With sodium phosphate buffer; DH-I and DH-II of Pseudomonas sp. TMY 1009; NAD; acetaldehyde; yeast alcohol dehydrogenase In water
alkaline lignin

alkaline lignin

A

styrene
292638-84-7

styrene

B

vanillin
121-33-5

vanillin

C

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With prolinium tetrachloromanganate(II); ethylammonium nitrate (EAN) at 35℃; for 6h;A n/a
B 12%
C n/a
Apocynol
2480-86-6

Apocynol

A

2-methoxy-1,4-benzoquinone
2880-58-2

2-methoxy-1,4-benzoquinone

B

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile for 0.5h; Microwave irradiation;A 11%
B 10%
With dihydrogen peroxide In water; acetonitrile at 39.84℃; for 0.25h; Reagent/catalyst;A 43 %Chromat.
B 52 %Chromat.
With dihydrogen peroxide In water; acetonitrile at 39.84℃; for 0.25h; Reagent/catalyst; Time;A 65 %Chromat.
B 19 %Chromat.
alkaline lignin

alkaline lignin

A

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

B

vanillin
121-33-5

vanillin

C

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With 1-butyl-3-methyl imidazolium tetrachloromanganate(II); ethylammonium nitrate (EAN) at 35℃; for 6h;A n/a
B 10%
C n/a
methyl magnesium iodide
917-64-6

methyl magnesium iodide

4-benzoyloxy-3-methoxybenzaldehyde
790-16-9

4-benzoyloxy-3-methoxybenzaldehyde

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
durch Ueberfuehrung in das Carbinol, Oxydation mit Kaliumdichromat und Schwefelsaeure zu 3-Methoxy-4-benzoyloxy-acetophenon und Verseifen durch Kochen mit verd.Natronlauge;
2-chloro-1-(4-hydroxy-3-methoxyphenyl)ethan-1-one
6344-28-1

2-chloro-1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With sulfuric acid; iron; sodium iodide
acetic acid
64-19-7

acetic acid

2-methoxy-phenol
90-05-1

2-methoxy-phenol

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With zinc(II) chloride
With aluminium trichloride; zinc(II) chloride at 140 - 150℃;
With boron trifluoride
With PPA
1-(3,4-dimethoxyphenyl)ethanone
1131-62-0

1-(3,4-dimethoxyphenyl)ethanone

A

3-hydroxy-4-methoxyacetophenone
6100-74-9

3-hydroxy-4-methoxyacetophenone

B

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With hydrogen bromide for 3h; Heating;A 0.2 g
B 0.05 g
Stage #1: 1-(3,4-dimethoxyphenyl)ethanone With aluminum (III) chloride; thiourea In dichloromethane for 5h; Heating / reflux;
Stage #2: With hydrogenchloride In dichloromethane; water at 20℃;
guaiacylglycerol-β-guaiacyl ether
7382-59-4

guaiacylglycerol-β-guaiacyl ether

A

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
2196-18-1

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

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

C

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With oxygen; rose bengal In acetonitrile at 13℃; Irradiation;A 28 % Chromat.
B 15 % Chromat.
C 30 % Chromat.
1-<3-methoxy-4-(methoxymethoxy)phenyl>ethanone
143418-77-3

1-<3-methoxy-4-(methoxymethoxy)phenyl>ethanone

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
hydrogenchloride In methanol Yield given;
4-acetyl-2-methoxyphenyl acetate
54771-60-7

4-acetyl-2-methoxyphenyl acetate

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With piperidine In 1,4-dioxane at 25℃; Kinetics; Deacetylation;
ω-chloro-4-oxy-3-methoxy-acetophenone

ω-chloro-4-oxy-3-methoxy-acetophenone

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With sulfuric acid; iron at 60℃;
benzyl chloride
100-44-7

benzyl chloride

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

4-benzyloxy-3-methoxyacetophenone
1835-11-6

4-benzyloxy-3-methoxyacetophenone

Conditions
ConditionsYield
With potassium phosphate; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; for 30h; Inert atmosphere;100%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 2h;100%
In pyridine at 5℃; for 0.166667h;99%
Methyl 4-bromobutyrate
4897-84-1

Methyl 4-bromobutyrate

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

methyl 4-(4-acetyl-2-methoxyphenoxy)butanoate
175281-79-5

methyl 4-(4-acetyl-2-methoxyphenoxy)butanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 16h; Ambient temperature;100%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 16h;100%
With potassium carbonate In N,N-dimethyl-formamide
With potassium carbonate In N,N-dimethyl-formamide for 16h; Inert atmosphere;
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

(4-acetyl-2-methoxy-phenoxy)acetic acid tert-butyl ester
188891-12-5

(4-acetyl-2-methoxy-phenoxy)acetic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;100%
Stage #1: 1-(3-methoxy-4-hydroxyphenyl)ethanone With sodium hydroxide In methanol at 20℃; for 15h;
Stage #2: bromoacetic acid tert-butyl ester In methanol for 15h; Reflux;
100%
With potassium carbonate In water; N,N-dimethyl-formamide at 0℃;99%
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

ethyl 4-(4-acetyl-2-methoxyphenoxy) butanoate
174884-21-0

ethyl 4-(4-acetyl-2-methoxyphenoxy) butanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 19h;100%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 19h;100%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 19h;100%
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

4-acetyl-2-methoxyphenyl trifluoromethanesulfonate
149105-13-5

4-acetyl-2-methoxyphenyl trifluoromethanesulfonate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12h;100%
acetic acid
64-19-7

acetic acid

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

4-acetyl-2-methoxyphenyl acetate
54771-60-7

4-acetyl-2-methoxyphenyl acetate

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 20℃; for 3h;100%
Methyl 4-bromobutyrate
4897-84-1

Methyl 4-bromobutyrate

potassium carbonate
584-08-7

potassium carbonate

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

methyl 4-(4-acetyl-2-methoxyphenoxy)butanoate
175281-79-5

methyl 4-(4-acetyl-2-methoxyphenoxy)butanoate

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide100%
In water; N,N-dimethyl-formamide100%
1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

2-methoxypyridin-3-yl-boronic acid
163105-90-6

2-methoxypyridin-3-yl-boronic acid

1-[3-methoxy-4-(2-methoxy-pyridin-3-yl)-phenyl]-ethanone
943152-72-5

1-[3-methoxy-4-(2-methoxy-pyridin-3-yl)-phenyl]-ethanone

Conditions
ConditionsYield
Stage #1: 1-(3-methoxy-4-hydroxyphenyl)ethanone With N,N-phenylbistrifluoromethane-sulfonimide; potassium carbonate In tetrahydrofuran at 120℃; for 0.1h; Irradiation;
Stage #2: 2-methoxypyridin-3-yl-boronic acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 120℃; for 0.166667h;
100%
1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

1-(3,4-dihydroxyphenyl)ethan-1-one
1197-09-7

1-(3,4-dihydroxyphenyl)ethan-1-one

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -78℃; for 0.25h; Inert atmosphere;100%
With aluminium(III) iodide; carbonic acid dimethyl ester In acetonitrile at 80℃; for 18h; Reagent/catalyst;97%
With aluminium(III) iodide; carbonic acid dimethyl ester In acetonitrile at 80℃; for 18h; Reagent/catalyst;97%
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

3-methoxy-4-(methoxymethyl)acetophenone

3-methoxy-4-(methoxymethyl)acetophenone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 21h;100%
benzyl bromide
100-39-0

benzyl bromide

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

4-benzyloxy-3-methoxyacetophenone
1835-11-6

4-benzyloxy-3-methoxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;99%
With potassium carbonate In N,N-dimethyl-formamide at 40℃;99%
With potassium carbonate In N,N-dimethyl-formamide at 40℃;99%
1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

methyl iodide
74-88-4

methyl iodide

1-(3,4-dimethoxyphenyl)ethanone
1131-62-0

1-(3,4-dimethoxyphenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;93.8%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;90.7%
With sodium hydroxide In N,N-dimethyl acetamide at 25℃; Rate constant;
With potassium carbonate In acetone at 20℃; for 4h;
polymer, 1.6 mmol/g NTf2 units; monomer(s): styrene; 1,4-bis(4-vinylphenoxy)butane; N-(4-vinylphenyl)trifluoromethanesulfonimide

polymer, 1.6 mmol/g NTf2 units; monomer(s): styrene; 1,4-bis(4-vinylphenoxy)butane; N-(4-vinylphenyl)trifluoromethanesulfonimide

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

4-acetyl-2-methoxyphenyl trifluoromethanesulfonate
149105-13-5

4-acetyl-2-methoxyphenyl trifluoromethanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;99%
1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

2,4-bis(trifluoromethyl)benzyl bromide
140690-56-8

2,4-bis(trifluoromethyl)benzyl bromide

1-[4-(2,4-bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-ethanone
885597-59-1

1-[4-(2,4-bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-ethanone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 15h;99%
benzene sulphochloride

benzene sulphochloride

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

3-methoxy-4-benzenesulphonyloxy-acetophenone
66338-49-6

3-methoxy-4-benzenesulphonyloxy-acetophenone

Conditions
ConditionsYield
With sodium hydroxide99%
With sodium hydroxide In water99%
allyl bromide
106-95-6

allyl bromide

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

1-(4-(allyloxy)-3-methoxyphenyl)ethanone
116218-80-5

1-(4-(allyloxy)-3-methoxyphenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate In ethanol at 70℃;98%
With potassium carbonate In acetone at 20℃; for 24h;98%
With potassium carbonate; acetone
With potassium carbonate In acetone Reflux;
With potassium carbonate In acetone for 3.16667h; Reflux;
1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

(R)-4-(1-hydroxyethyl)-2-methoxyphenol

(R)-4-(1-hydroxyethyl)-2-methoxyphenol

Conditions
ConditionsYield
With N(CH2)3CHCPh2OBO(n-Oct)98%
With octanol; (S)-diphenylprolinol; dimethylsulfide borane complex In toluene at 34℃;98%
1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

trimethyleneglycol
504-63-2

trimethyleneglycol

2-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,3-dioxane

2-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,3-dioxane

Conditions
ConditionsYield
With Triisopropoxymethan; cerium triflate In hexane at 25℃; for 3h;98%
propargyl bromide
106-96-7

propargyl bromide

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

1-(3-methoxy-4-(prop-2-yn-1-yloxy)phenyl)ethan-1-one
956597-80-1

1-(3-methoxy-4-(prop-2-yn-1-yloxy)phenyl)ethan-1-one

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 25℃; for 12h;98%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 16h;98%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;98%
2-formylbenzo[b]furan
4265-16-1

2-formylbenzo[b]furan

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

(E)-3-(benzofuran-2-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one

(E)-3-(benzofuran-2-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 72h; Claisen-Schmidt Condensation; Inert atmosphere;98%
furfural
98-01-1

furfural

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

(E)-3-(furan-2-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one

(E)-3-(furan-2-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 72h; Claisen-Schmidt Condensation; Inert atmosphere;98%
With potassium hydroxide In ethanol at 0 - 20℃; for 73h; Claisen-Schmidt Condensation; Inert atmosphere;89%
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

(E)-1-(4-hydroxy-3-methoxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one

(E)-1-(4-hydroxy-3-methoxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 72h; Claisen-Schmidt Condensation; Inert atmosphere;98%
With potassium hydroxide In ethanol at 0 - 20℃; for 73h; Claisen-Schmidt Condensation; Inert atmosphere;61%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

(2E,4E)-1-(4-hydroxy-3-methoxyphenyl)-5-phenylpenta-2,4-dien-1-one

(2E,4E)-1-(4-hydroxy-3-methoxyphenyl)-5-phenylpenta-2,4-dien-1-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; Claisen-Schmidt Condensation;98%
acetic anhydride
108-24-7

acetic anhydride

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

4-acetyl-2-methoxyphenyl acetate
54771-60-7

4-acetyl-2-methoxyphenyl acetate

Conditions
ConditionsYield
With pyridine In dichloromethane Ambient temperature;97%
In pyridine for 18h; Acetylation;
With pyridine; dmap In dichloromethane
1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

3-methoxy-4-toluenesulphonyloxy-acetophenone

3-methoxy-4-toluenesulphonyloxy-acetophenone

Conditions
ConditionsYield
With sodium hydroxide In 2-methylbenzenesulphochloride; water97%
N-tert-butoxycarbonyl-L-methionine
2488-15-5

N-tert-butoxycarbonyl-L-methionine

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

C19H27NO6S

C19H27NO6S

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;97%
1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

1-Bromooctadecane
112-89-0

1-Bromooctadecane

1-(3-methoxy-4-(octadecyloxy)phenyl)ethanone
1603965-07-6

1-(3-methoxy-4-(octadecyloxy)phenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 60℃;96.7%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

4'-tert-butyldimethylsilyloxy-3'-methoxyacetophenone
132255-78-8

4'-tert-butyldimethylsilyloxy-3'-methoxyacetophenone

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 3h; Ambient temperature;96%
With 1H-imidazole at 20℃;95%
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

1-<3-methoxy-4-(methoxymethoxy)phenyl>ethanone
143418-77-3

1-<3-methoxy-4-(methoxymethoxy)phenyl>ethanone

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃;96%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 6h;62%
With sodium hydride 1.) THF, DMF, RT, 3 h, 2.) THF, DMF, RT, 2 h; Yield given. Multistep reaction;
ethyl iodide
75-03-6

ethyl iodide

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

1-<(4-ethoxy-3-methoxy)phenyl>ethan-1-one
75665-89-3

1-<(4-ethoxy-3-methoxy)phenyl>ethan-1-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 2h;96%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;96%
With potassium carbonate In acetone for 2h; Heating;80%

498-02-2Relevant articles and documents

UV cell stress induces oxidative cyclization of a protective reagent for DNA damage reduction in skin explants

Liu, Jing,Zhu, Haizhou,Premnauth, Gurdat,Earnest, Kaylin G.,Hahn, Patricia,Gray, George,Queenan, Jack A.,Prevette, Lisa E.,AbdulSalam, Safnas F.,Kadekaro, Ana Luisa,Merino, Edward J.

, p. 133 - 138 (2019)

UV irradiation is a major driver of DNA damage and ultimately skin cancer. UV exposure leads to persistent radicals that generate ROS over prolonged periods of time. Toward the goal of developing long-lasting antioxidants that can penetrate skin, we have designed a ROS-initiated protective (RIP) reagent that, upon reaction with ROS (antioxidant activity), self-cyclizes and then releases the natural product apocynin. Apocynin is a known antioxidant and inhibitor of NOX oxidase enzymes. A key phenol on the compound 1 controls ROS-initiated cyclization and makes 1 responsive to ROS with a EC50 comparable to common antioxidants in an ABTS assay. In an in vitro DNA nicking assay, the RIP reagent prevented DNA strand breaks. In cell-based assays, the reagent was not cytotoxic, apocynin was released only in cells treated with UVR, reduced UVR-induced cell death, and lowered DNA lesion formation. Finally, topical treatment of human skin explants with the RIP reagent reduced UV-induced DNA damage as monitored by quantification of cyclobutane dimer formation and DNA repair signaling via TP53. The reagent was more effective than administration of a catalase antioxidant on skin explants. This chemistry platform will expand the types of ROS-activated motifs and enable inhibitor release for potential use as a long-acting sunscreen.

Room temperature depolymerization of lignin using a protic and metal based ionic liquid system: an efficient method of catalytic conversion and value addition

Mehta, Mohit J.,Kulshrestha, Akshay,Sharma, Shweta,Kumar, Arvind

, p. 1240 - 1247 (2021/02/26)

Lignin is one of the most abundant biopolymer which can be utilized to synthesize various chemicalsviaits depolymerization. However, depolymerization of lignin generally occurs under very harsh conditions. Herein, we report the efficient depolymerization of ligninviadissolution in a mixed ionic liquid system: ethyl ammonium nitrate (EAN) + prolinium tetrachloromanganate(ii) [Pro]2[MnCl4] at 35 °C and under atmospheric pressure conditions. The high dissolution of lignin in ethyl ammonium nitrate provided a large number of H-bonding sites leading to the cracking of lignin and subsequent oxidative conversion by [Pro]2[MnCl4]viathe formation of metal-oxo bonding between Mn and lignin molecules. The extracted yield of vanillin was found to be 18-20% on lignin weight basisviaGC-MS analysis. The depolymerization of lignin was confirmed by SEM, FT-IR and PXRD analysis. Since lignin contains UV-absorbing functional groups, the regenerated biomass after the recovery of the depolymerized products was further utilized to synthesize a UV-shielding material. The constructed films from such a material exhibited a high SPF value of 22 and were found to be very effective by limiting the UV degradation of rhodamine B thus making the lignin valorization process economically viable and environmentally sustainable.

Discovery, Biocatalytic Exploration and Structural Analysis of a 4-Ethylphenol Oxidase from Gulosibacter chungangensis

Alvigini, Laura,Fraaije, Marco W.,Gran-Scheuch, Alejandro,Guo, Yiming,Mattevi, Andrea,Saifuddin, Mohammad,Trajkovic, Milos

, p. 3225 - 3233 (2021/10/04)

The vanillyl-alcohol oxidase (VAO) family is a rich source of biocatalysts for the oxidative bioconversion of phenolic compounds. Through genome mining and sequence comparisons, we found that several family members lack a generally conserved catalytic aspartate. This finding led us to study a VAO-homolog featuring a glutamate residue in place of the common aspartate. This 4-ethylphenol oxidase from Gulosibacter chungangensis (Gc4EO) shares 42 % sequence identity with VAO from Penicillium simplicissimum, contains the same 8α-N3-histidyl-bound FAD and uses oxygen as electron acceptor. However, Gc4EO features a distinct substrate scope and product specificity as it is primarily effective in the dehydrogenation of para-substituted phenols with little generation of hydroxylated products. The three-dimensional structure shows that the characteristic glutamate side chain creates a closely packed environment that may limit water accessibility and thereby protect from hydroxylation. With its high thermal stability, well defined structural properties and high expression yields, Gc4EO may become a catalyst of choice for the specific dehydrogenation of phenolic compounds bearing small substituents.

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