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2478-38-8

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2478-38-8 Usage

Uses

Different sources of media describe the Uses of 2478-38-8 differently. You can refer to the following data:
1. 4’-Hydroxy-3’,5’-dimethoxyacetophenone used in the synthesis of tetramethoxychalcone and its analogues as anticancer agents. It is a naturally occuring compound found in plants and used in plant-pathogen recognition.
2. insect attractant, plant hormone
3. A buffer also known as acetosyringone that is used in the synthesis of tetramethoxychalcone and its analogues as anticancer agents in vitro.

Description

Acetosyringone is a phenol secreted by wounded plant tissues. It induces expression of virulence A genes and chemotaxis in A. tumefaciens strains that contain a tumor-inducing plasmid used to transfer genetic information to plant cells. Acetosyringone is widely used to increase efficacy of genetic transformation for the creation of genetically modified dicotyledonous and monocotyledonous plants.

Chemical Properties

beige to light brown crystalline powder

Preparation

Preparation by adding a solution of 4-hydroxy-3- iodo-5-methoxyacetophenone and cupric chloride in DMF to a solution of sodium methoxide in methanol and heating between 105° and 120° (86%).

Definition

ChEBI: A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.

Check Digit Verification of cas no

The CAS Registry Mumber 2478-38-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,7 and 8 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 2478-38:
(6*2)+(5*4)+(4*7)+(3*8)+(2*3)+(1*8)=98
98 % 10 = 8
So 2478-38-8 is a valid CAS Registry Number.

2478-38-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (B22634)  4'-Hydroxy-3',5'-dimethoxyacetophenone, 97%   

  • 2478-38-8

  • 1g

  • 354.0CNY

  • Detail
  • Alfa Aesar

  • (B22634)  4'-Hydroxy-3',5'-dimethoxyacetophenone, 97%   

  • 2478-38-8

  • 5g

  • 1096.0CNY

  • Detail
  • Alfa Aesar

  • (B22634)  4'-Hydroxy-3',5'-dimethoxyacetophenone, 97%   

  • 2478-38-8

  • 25g

  • 4562.0CNY

  • Detail

2478-38-8SDS

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 acetosyringone

1.2 Other means of identification

Product number -
Other names 1-(4-hydroxy-3,5-dimethoxyphenyl)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:2478-38-8 SDS

2478-38-8Synthetic route

methyl (3,4,5-trimethoxyphenyl) ketone
1136-86-3

methyl (3,4,5-trimethoxyphenyl) ketone

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
With lithium thioethoxide In N,N-dimethyl-formamide at 70℃; for 0.25h; Inert atmosphere; Microwave irradiation; regioselective reaction;95%
With magnesium iodide for 0.5h; neat (no solvent);90%
With zirconium(IV) chloride; methoxybenzene In dichloromethane at 40℃; for 48h; Sealed tube;63%
methyl 4-O-tert-butyldimethylsilyl-3,5-dimethoxybenzoate
383176-01-0

methyl 4-O-tert-butyldimethylsilyl-3,5-dimethoxybenzoate

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride92%
1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanol
33900-62-8

1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanol

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
With copper diacetate; ethylene glycol at 50℃; for 8h; Green chemistry; chemoselective reaction;91%
4-ethylsyringol
14059-92-8

4-ethylsyringol

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
With copper diacetate; ethylene glycol at 90℃; for 12h; Green chemistry; chemoselective reaction;84%
C11H16O4
1105671-50-8

C11H16O4

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
With copper diacetate; ethylene glycol at 50℃; for 8h; Green chemistry; chemoselective reaction;83%
1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanol
33900-62-8

1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanol

A

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

B

2,6-dimethoxy-p-quinone
530-55-2

2,6-dimethoxy-p-quinone

Conditions
ConditionsYield
With oxygen; (pyridine)cobalt In methanol under 2585.7 Torr; for 24h; Ambient temperature; Title compound not separated from byproducts;A 4 % Spectr.
B 82%
With oxygen; (pyridine)cobalt In methanol under 2585.7 Torr; for 24h; Ambient temperature;A 4 % Spectr.
B 82%
acetic acid 2,6-dimethoxy-phenyl ester
944-99-0

acetic acid 2,6-dimethoxy-phenyl ester

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In toluene for 1h; Fries rearrangement; Heating;80%
With aluminum (III) chloride In nitrobenzene at 0℃; Solvent; Reagent/catalyst;80%
With aluminium trichloride; nitrobenzene at 2 - 3℃; dann bei Zimmertemperatur;
With aluminium trichloride; nitrobenzene
With aluminium trichloride In nitrobenzene
3,3'-dimethoxy-4-carboxymethoxyacetophenone
871798-98-0

3,3'-dimethoxy-4-carboxymethoxyacetophenone

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Stage #1: 3,3'-dimethoxy-4-carboxymethoxyacetophenone With triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius rearrangement; Heating;
Stage #2: With potassium hydroxide; glycerol In ethanol; N,N-dimethyl-formamide; toluene for 2h; Heating; Further stages.;
70%
1-(4-hydroxy-3-iodo-5-methoxy-phenyl)ethan-1-one
103440-59-1

1-(4-hydroxy-3-iodo-5-methoxy-phenyl)ethan-1-one

sodium methylate
124-41-4

sodium methylate

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
With methanol; copper at 140℃;
1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone benzyl ether
76246-81-6

1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone benzyl ether

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
With hydrogen bromide; acetic acid bei gewoehnlicher Temperatur;
1,3-dimethoxy-2-hydroxy-benzene
91-10-1

1,3-dimethoxy-2-hydroxy-benzene

acetic acid
64-19-7

acetic acid

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
With boron trifluoride
pyrrolidine
123-75-1

pyrrolidine

1-(4-acetoxy-3,5-dimethoxy-phenyl)-ethanone
28294-47-5

1-(4-acetoxy-3,5-dimethoxy-phenyl)-ethanone

A

N-(acetyl)pyrrolidine
4030-18-6

N-(acetyl)pyrrolidine

B

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
for 0.05h; Ambient temperature;
1,3-dimethoxy-2-hydroxy-benzene
91-10-1

1,3-dimethoxy-2-hydroxy-benzene

acetyl chloride
75-36-5

acetyl chloride

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
(i), (ii) AlCl3, PhNO2; Multistep reaction;
4-amino-butyric acid 2-(4-hydroxy-3,5-dimethoxy-phenyl)-2-oxo-ethyl ester
284043-12-5

4-amino-butyric acid 2-(4-hydroxy-3,5-dimethoxy-phenyl)-2-oxo-ethyl ester

A

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

B

3',5'-dimethoxy-4'-hydroxy-(2-hydroxy)acetophenone
90426-22-5

3',5'-dimethoxy-4'-hydroxy-(2-hydroxy)acetophenone

C

4-amino-n-butyric acid
56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
With water Hydrolysis; reduction; UV-irradiation;
forest plant material

forest plant material

A

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

B

(E)-sinapinaldehyde
4206-58-0

(E)-sinapinaldehyde

C

1-(3,5-dimethoxy-4-hydroxyphenyl)propan-2-one
19037-58-2

1-(3,5-dimethoxy-4-hydroxyphenyl)propan-2-one

D

2-(4-hydroxy-3,5-dimethoxyphenyl)acetaldehyde

2-(4-hydroxy-3,5-dimethoxyphenyl)acetaldehyde

Conditions
ConditionsYield
With air Oxidation; Formation of xenobiotics; Further byproducts given;
1-(3,5-dimethoxyphenyl)ethan-1-one
39151-19-4

1-(3,5-dimethoxyphenyl)ethan-1-one

A

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

B

2ʹ-hydroxy-3ʹ,5ʹ-dimethoxyacetophenone
17605-00-4

2ʹ-hydroxy-3ʹ,5ʹ-dimethoxyacetophenone

Conditions
ConditionsYield
With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid In acetonitrile at 80℃; for 2h;A 3 % Chromat.
B 11 % Chromat.
γ-O-(3,5-dimethoxy-4-hydroxyphenacyl) L-glutamate, trifluoroacetate salt

γ-O-(3,5-dimethoxy-4-hydroxyphenacyl) L-glutamate, trifluoroacetate salt

A

L-glutamic acid
56-86-0

L-glutamic acid

B

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

C

3',5'-dimethoxy-4'-hydroxy-(2-hydroxy)acetophenone
90426-22-5

3',5'-dimethoxy-4'-hydroxy-(2-hydroxy)acetophenone

Conditions
ConditionsYield
With water Hydrolysis; reduction; UV-irradiation;
2-bromo-1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
51149-28-1

2-bromo-1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: DBU / dioxane / 12 h / 0 - 20 °C
2: TFA / 4 h / 0 °C
3: H2O / UV-irradiation
View Scheme
Multi-step reaction with 3 steps
1: 67 percent / DBU / benzene / 12 h / 20 °C
2: 98 percent / TFA / 4 h / 0 °C
3: H2O / UV-irradiation
View Scheme
4-tert-butoxycarbonylamino-butyric acid 2-(4-hydroxy-3,5-dimethoxy-phenyl)-2-oxo-ethyl ester
284043-14-7

4-tert-butoxycarbonylamino-butyric acid 2-(4-hydroxy-3,5-dimethoxy-phenyl)-2-oxo-ethyl ester

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TFA / 4 h / 0 °C
2: H2O / UV-irradiation
View Scheme
γ-O-(3,5-dimethoxy-4-hydroxyphenacyl) t-butyl N-t-boc L-glutamate
284043-08-9

γ-O-(3,5-dimethoxy-4-hydroxyphenacyl) t-butyl N-t-boc L-glutamate

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / TFA / 4 h / 0 °C
2: H2O / UV-irradiation
View Scheme
1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

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

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous KI; NaHCO3; iodine
2: copper; methanol / 140 °C
View Scheme
1,3-dimethoxy-2-hydroxy-benzene
91-10-1

1,3-dimethoxy-2-hydroxy-benzene

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine; benzene / anschliessendes Erwaermen auf 60grad
2: AlCl3; nitrobenzene
View Scheme
3,5-dimethoxy-4-hydroxybenzoic acid
530-57-4

3,5-dimethoxy-4-hydroxybenzoic acid

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: NaOH-solution
2: benzene; phosphorus pentachloride / 0 °C
3: alcohol; diethyl ether
4: ammonium chloride; diluted ammonia
5: water / 175 - 180 °C
6: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur
View Scheme
methyl 4-benzyloxy-3,5-dimethoxybenzoate
27065-65-2

methyl 4-benzyloxy-3,5-dimethoxybenzoate

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: NaOH-solution / durch Verseifung
2: benzene; phosphorus pentachloride / 0 °C
3: alcohol; diethyl ether
4: ammonium chloride; diluted ammonia
5: water / 175 - 180 °C
6: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur
View Scheme
methyl syringate
884-35-5

methyl syringate

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: methanolic KOH-solution
2: NaOH-solution / durch Verseifung
3: benzene; phosphorus pentachloride / 0 °C
4: alcohol; diethyl ether
5: ammonium chloride; diluted ammonia
6: water / 175 - 180 °C
7: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur
View Scheme
ethyl 3-(4-benzyloxy-3,5-dimethoxyphenyl)-3-oxopropionate
30835-78-0

ethyl 3-(4-benzyloxy-3,5-dimethoxyphenyl)-3-oxopropionate

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water / 175 - 180 °C
2: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur
View Scheme
4-benzyloxy-3,5-dimethoxybenzoic acid chloride
14588-61-5

4-benzyloxy-3,5-dimethoxybenzoic acid chloride

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: alcohol; diethyl ether
2: ammonium chloride; diluted ammonia
3: water / 175 - 180 °C
4: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur
View Scheme
2-(4-benzyloxy-3,5-dimethoxy-benzoyl)-3-oxo-butyric acid ethyl ester
860579-04-0

2-(4-benzyloxy-3,5-dimethoxy-benzoyl)-3-oxo-butyric acid ethyl ester

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium chloride; diluted ammonia
2: water / 175 - 180 °C
3: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur
View Scheme
4-(benzyloxy)-3,5-dimethoxybenzoic acid
14588-60-4

4-(benzyloxy)-3,5-dimethoxybenzoic acid

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: benzene; phosphorus pentachloride / 0 °C
2: alcohol; diethyl ether
3: ammonium chloride; diluted ammonia
4: water / 175 - 180 °C
5: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur
View Scheme
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

acetyl chloride
75-36-5

acetyl chloride

1-(4-acetoxy-3,5-dimethoxy-phenyl)-ethanone
28294-47-5

1-(4-acetoxy-3,5-dimethoxy-phenyl)-ethanone

Conditions
ConditionsYield
With potassium carbonate; triethylamine In dichloromethane99%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

3,5-bis(trifluoromethyl)benzyl bromide
32247-96-4

3,5-bis(trifluoromethyl)benzyl bromide

1-[4-(3,5-Bis-trifluoromethyl-benzyloxy)-3,5-dimethoxy-phenyl]-ethanone

1-[4-(3,5-Bis-trifluoromethyl-benzyloxy)-3,5-dimethoxy-phenyl]-ethanone

Conditions
ConditionsYield
With sodium hydroxide In water; acetonitrile for 5h; Heating;95%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

3′,5′-dimethoxy-4′-hydroxyacetophenone oxime

3′,5′-dimethoxy-4′-hydroxyacetophenone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In methanol; water at 60℃;93%
With hydroxylamine hydrochloride; sodium acetate In water at 80℃; for 2h;47%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

ethyl bromoacetate
105-36-2

ethyl bromoacetate

ethyl (4-acetyl-2,6-dimethoxyphenoxy)acetate
383176-05-4

ethyl (4-acetyl-2,6-dimethoxyphenoxy)acetate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 18h;90%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

2-(tert-butyldimethylsilyloxy)ethanol
102229-10-7

2-(tert-butyldimethylsilyloxy)ethanol

1-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,5-dimethoxy-phenyl}-ethanone

1-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,5-dimethoxy-phenyl}-ethanone

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction;87%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

1-(4-hydroxy-3,5-dimethoxyphenyl)-2-iodoethanone

1-(4-hydroxy-3,5-dimethoxyphenyl)-2-iodoethanone

Conditions
ConditionsYield
With iodine; Selectfluor In methanol at 22℃; for 24h;81%
9-methyl-9H-carbazole-3-carbaldehyde
21240-56-2

9-methyl-9H-carbazole-3-carbaldehyde

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

(E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(9-methyl-9H-carbazol-6-yl)prop-2-en-1-one

(E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(9-methyl-9H-carbazol-6-yl)prop-2-en-1-one

Conditions
ConditionsYield
With piperidine In ethanol for 3h; Claisen-Schmidt Condensation; Reflux;79%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

ethylene glycol
107-21-1

ethylene glycol

2,6-dimethoxy-4-(2-methyl-[1,3]dioxolan-2-yl)-phenol
926907-08-6

2,6-dimethoxy-4-(2-methyl-[1,3]dioxolan-2-yl)-phenol

Conditions
ConditionsYield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester75%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

C10H15IO
1189796-80-2

C10H15IO

C20H25IO5

C20H25IO5

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane69%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

2-bromo-1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
51149-28-1

2-bromo-1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone

Conditions
ConditionsYield
With copper(ll) bromide In chloroform; ethyl acetate at 20℃; for 21h; Bromination;68%
With bromine In chloroform
With bromine In 1,4-dioxane; diethyl ether at 0℃; for 1h;
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

isopropyl bromide
75-26-3

isopropyl bromide

3',5'-dimethoxy-4'-isopropoxyacetophenone
120448-71-7

3',5'-dimethoxy-4'-isopropoxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 4.5h; Heating;65.9%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

4-(bis(2,4,6-trimethoxyphenyl)methyl)-2,6-dimethoxyphenol

4-(bis(2,4,6-trimethoxyphenyl)methyl)-2,6-dimethoxyphenol

Conditions
ConditionsYield
Stage #1: 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone With selenium(IV) oxide; ytterbium(III) chloride In water; dimethyl sulfoxide at 110℃; for 15h; Green chemistry;
Stage #2: 1,2,3-trimethoxybenzene In water; dimethyl sulfoxide at 70℃; for 0.166667h; Green chemistry;
65%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

DL-tryptophan methyl ester
7303-49-3

DL-tryptophan methyl ester

C22H18N2O6
1638141-24-8

C22H18N2O6

Conditions
ConditionsYield
Stage #1: 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone With iodine; dimethyl sulfoxide at 90℃;
Stage #2: DL-tryptophan methyl ester
64%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

A

1-(3,4-dihydroxy-5-methoxyphenyl)-ethan-1-one
3934-89-2

1-(3,4-dihydroxy-5-methoxyphenyl)-ethan-1-one

B

1-(3,4,5-trihydroxyphenyl)-ethan-1-one
33709-29-4

1-(3,4,5-trihydroxyphenyl)-ethan-1-one

Conditions
ConditionsYield
With methylimidazolium bromide at 110℃; Irradiation;A 63%
B 26%
Methyl 4-bromobutyrate
4897-84-1

Methyl 4-bromobutyrate

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

4-(4-Acetyl-2,6-dimethoxy-phenoxy)-butyric acid methyl ester
159645-64-4

4-(4-Acetyl-2,6-dimethoxy-phenoxy)-butyric acid methyl ester

Conditions
ConditionsYield
60%
With 18-crown-6 ether; potassium carbonate In butanone 1.) reflux, 48 h, 2.) reflux, 1 h;60%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxyphenyl)-prop-2-enone
172302-30-6

1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxyphenyl)-prop-2-enone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 24h;60%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

2CF3O2S(1-)*Zn(2+)*2H2O

2CF3O2S(1-)*Zn(2+)*2H2O

1-[4-hydroxy-3,5-dimethoxy-2-(trifluoromethyl)phenyl]ethan-1-one

1-[4-hydroxy-3,5-dimethoxy-2-(trifluoromethyl)phenyl]ethan-1-one

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper(l) iodide; hydroquinone In water; dimethyl sulfoxide at 30℃; for 24h; pH=5.5; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube;58%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

(E)-2-allyl-6-iodohepta-2,6-dienoic acid
1189796-72-2

(E)-2-allyl-6-iodohepta-2,6-dienoic acid

C20H23IO6
1189796-73-3

C20H23IO6

Conditions
ConditionsYield
Stage #1: (E)-2-allyl-6-iodohepta-2,6-dienoic acid With diphenic acid; lead(IV) tetraacetate In dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone In dichloromethane at 0 - 20℃; for 2.25h;
54%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

(E)-2-allyl-6-bromohepta-2,6-dienoic acid

(E)-2-allyl-6-bromohepta-2,6-dienoic acid

C20H23BrO6
1189796-74-4

C20H23BrO6

Conditions
ConditionsYield
Stage #1: (E)-2-allyl-6-bromohepta-2,6-dienoic acid With diphenic acid; lead(IV) tetraacetate In dichloromethane for 0.333333h; Inert atmosphere;
Stage #2: 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone In dichloromethane at 0 - 20℃; for 1.41667h;
48%
isovanillin
621-59-0

isovanillin

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

(E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
1197288-80-4

(E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one

Conditions
ConditionsYield
Stage #1: isovanillin; 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone In ethanol at 20℃; for 0.0833333h;
Stage #2: With sodium hydroxide In ethanol at 20℃;
48%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

phenyl 2,3,4,6-tetra-O-benzyl-1-sulfinyl-α/β-D-glucopyranoside
122795-89-5

phenyl 2,3,4,6-tetra-O-benzyl-1-sulfinyl-α/β-D-glucopyranoside

1-[3,5-Dimethoxy-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-ethanone

1-[3,5-Dimethoxy-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-ethanone

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 20℃;46%
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

C11H17IO2

C11H17IO2

C21H27IO6

C21H27IO6

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 2.5h; Inert atmosphere;34%

2478-38-8Relevant articles and documents

Detection of an O-methyltransferase synthesising acetosyringone in methyl jasmonate-treated tobacco cell-suspensions cultures

Negrel, Jonathan,Javelle, Francine,Wipf, Daniel

, p. 52 - 60 (2014)

Acetosyringone (3′,5′-dimethoxy-4′-hydroxyacetophenone) is a well-known and very effective inducer of the virulence genes of Agrobacterium tumefaciens but the precise pathway of its biosynthesis in plants is still unknown. We have used two tobacco cell lines, cultured in suspension and exhibiting different patterns of accumulation of acetosyringone in their culture medium upon treatment with methyl jasmonate, to study different steps of acetosyringone biosynthesis. In the two cell lines studied, treatment with 100 μM methyl jasmonate triggered a rapid and transient increase in acetovanillone synthase activity followed by a progressive increase in S-adenosyl-L-methionine: 5-hydroxyacetovanillone 5-O-methyltransferase activity which paralleled the rise in acetosyringone concentration in the culture medium. This O-methyltransferase displayed Michaelis-Menten kinetics with an apparent Km value of 18 μM for 5-hydroxyacetovanillone and its activity was magnesium-independent. Its molecular mass was estimated by gel permeation on an FPLC column and was found to be of ca. 81 kDa. 5-Hydroxyacetovanillone was the best substrate among the different o-diphenolic compounds tested as methyl acceptors in the O-methyltransferase assay. No formation of 5- hydroxyacetovanillone could be detected in vitro from 5-hydroxyferuloyl-CoA and NAD in the extracts used to measure acetovanillone synthase activity, indicating that 5-hydroxyacetovanillone is probably formed by direct hydroxylation of acetovanillone rather than by β-oxidation of 5-hydroxyferulic acid. Taken together our results strongly support the hypothesis that acetosyringone biosynthesis in tobacco proceeds from feruloyl-CoA via acetovanillone and 5-hydroxyacetovanillone.

Catalytic C(β)-O Bond Cleavage of Lignin in a One-Step Reaction Enabled by a Spin-Center Shift

Zhu, Qilei,Nocera, Daniel G.

, p. 14181 - 14187 (2021/11/27)

A challenge to the utilization of lignin as a feedstock for aromatic fine chemicals lies in selective cleavage of copious β-O-4 linkages. A photocatalytic strategy for the selective cleavage of the C(β)-O bonds of model substrates and natural lignin extracts is achieved by a redox-neutral, catalytic cycle that does not require stoichiometric reagents. Mechanistic studies reveal the generation of a thiyl radical, which is derived from a cystine-derived H-atom transfer catalyst, initiates a spin-center shift (SCS) that leads to C(β)-O bond cleavage. The SCS reactivity is reminiscent of the C(β)-O bond cleavage chemistry that occurs in the active site of ribonucleotide reductase.

Profiling of the formation of lignin-derived monomers and dimers from: Eucalyptus alkali lignin

Hu, Zhenhua,Li, Suxiang,Lu, Fachuang,Shi, Lanlan,Wang, Chen,Yue, Fengxia,Zhang, Han,Zhao, Chengke

supporting information, p. 7366 - 7375 (2020/11/18)

Lignin is a renewable and the most abundant aromatic source that can be used for extensive chemicals and materials. Although approximately 50 million tons of lignin are produced annually as a by-product of the pulp and paper industry, it is currently underutilized. It is important to know the structural features of technical lignin when considering its application. In this work, we have demonstrated the formation of low-molecular-weight constituents from hardwood (Eucalyptus) lignin, which produces much more low-molecular-weight constituents than softwood (spruce) lignin, after a chemical pulping process, and analyzed the micromolecular compositions in the alkali lignin after fractionation by dichloromethane (DCM) extraction. By applying analytical methods (gel-permeation chromatography, 2D NMR and GC-MS) with the aid of evidence from authenticated compounds, a great treasure trove of lignin-derived phenolic compounds from Eucalyptus alkali lignin were disclosed. Except for some common monomeric products, as many as 15 new lignin-derived monomers and dimers including syringaglycerol, diarylmethane, 1,2-diarylethanes, 1,2-diarylethenes, (arylvinyl ether)-linked arylglycerol dimers and isomeric syringaresinols were identified in the DCM-soluble fraction. Regarding the formation and evolution of the Cα-condensed β-aryl ether structure, a novel route that is potentially responsible for the high content of β-1 diarylethenes and diarylethanes in the lignin low-molecular-weight fraction, in addition to the β-1 (spirodienone) pathway, was proposed. This work not only provides novel insights into the chemical transformation of S-G lignin during the alkali pulping process, but also discovered lignin-derived phenolic monomers and dimers that can potentially be used as raw materials in the chemical or pharmaceutical industries. This journal is

Synthesis of CoFeO mixed oxides via an alginate gelation process as efficient heterogeneous catalysts for lignin depolymerization in water

Hdidou,Khallouk,Solhy,Manoun,Oukarroum,Barakat

, p. 5445 - 5453 (2018/11/20)

A catalytic oxidative fragmentation of a lignin dimer and polymer extracted from wheat straw was successfully performed under eco-friendly conditions: 10% O2/N2 as the oxidizing agent, water as the solvent (pH ≈ 7), and Co3O4, Fe2O3 and CoFeO mixed oxides as heterogeneous catalysts and at temperatures of T = 150 °C and 200 °C. These catalysts unexpectedly showed tunable selectivity that directly depends on the composition of the selected bimetallic nanoparticles. High selectivity for benzoic acid and alkylbenzene (above 50%) was observed over Co50-Fe50 at 200 °C. Under similar conditions, the conversion of wheat organosolv lignin over Co50-Fe50 at 150 °C for 4 h yielded up to 50 wt% of monomeric species (based on dry lignin) and up to 19% of aromatic molecules with high selectivity to aromatic aldehydes (syringaldehyde and vanillin), up to 60%. An important fraction of water-soluble oligomers, with low molecular weights, was also formed during the catalytic treatment. The oxide nanomaterials were readily separated from the residual lignin during the recyclability test. The yield and the product distribution can be tuned by choosing the oxidation parameters: temperature, reaction time, oxygen partial pressure, solvent and catalyst charges.

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