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3943-74-6

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3943-74-6 Usage

Chemical Properties

pale yellow to beige powder and granules

Uses

Different sources of media describe the Uses of 3943-74-6 differently. You can refer to the following data:
1. Methyl Vanillate maintains antimicrobial properties due to the phenylpropanoid moiety in the structure.
2. Methyl vanillate is used to investigate the volatile compounds of heather honeys from Calluna vulgaris and Erica arborea.
3. Methyl vanillate was used to investigate the volatile compounds of heather honeys from Calluna vulgaris and Erica arborea.

Definition

ChEBI: A benzoate ester that is the methyl ester of vanillic acid.

General Description

Methyl vanillate is a volatile compound present in cloudberries (Rubus Chamaemorus.).

Check Digit Verification of cas no

The CAS Registry Mumber 3943-74-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,9,4 and 3 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3943-74:
(6*3)+(5*9)+(4*4)+(3*3)+(2*7)+(1*4)=106
106 % 10 = 6
So 3943-74-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3

3943-74-6SDS

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 methyl vanillate

1.2 Other means of identification

Product number -
Other names Methyl Vanillate

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:3943-74-6 SDS

3943-74-6Synthetic route

methanol
67-56-1

methanol

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

3-methoxy-4-hydroxybenzoic acid

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

4-hydroxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride for 12h; Reflux;100%
With hydrogenchloride In diethyl ether Fischer-Speier Esterification; Reflux;100%
With thionyl chloride at 0 - 20℃; Inert atmosphere;100%
methyl 4-(benzyloxy)-3-methoxybenzoate
56441-97-5

methyl 4-(benzyloxy)-3-methoxybenzoate

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

4-hydroxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In various solvent(s) at 20℃; under 760 Torr; for 6h;95%
methanol
67-56-1

methanol

vanillin
121-33-5

vanillin

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

4-hydroxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
With perchloric acid; sodium percarbonate; vanadia for 2h; Cooling;94%
With 2,2':6,2''-terpyridine; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate; sodium hydroxide at 90℃; for 24h; Green chemistry; chemoselective reaction;83%
With 1-(ferrocenylbutyl)-4-(3-methylimidazolium) tetrafluoroborate; iodine; potassium carbonate at 50 - 60℃; for 22h; Inert atmosphere;40%
With oxygen; methylene blue at 10 - 15℃; for 144h; Mechanism; Irradiation; also with EtOH; also without irradiation in the presence of p-toluenesulfonic acid;
With perchloric acid; dihydrogen peroxide; vanadia In water at 5℃; for 6h; oxidative esterification;83 % Chromat.
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

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

3-methoxy-4-hydroxybenzoic acid

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

4-hydroxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
microwave irradiation;90%
3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

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

4-hydroxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid; sodium hydrogencarbonate; mercury In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate82%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

2-methoxy-phenol
90-05-1

2-methoxy-phenol

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

4-hydroxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; oxygen; potassium carbonate; potassium iodide at 100℃; under 6000.6 Torr; for 18h;76%
methanol
67-56-1

methanol

seguinoside E

seguinoside E

A

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

4-hydroxy-3-methoxybenzoic acid methyl ester

B

4-hydroxyphenyl β-D-apiofuranosyl-(1->2)-O-β-D-glucopyranoside

4-hydroxyphenyl β-D-apiofuranosyl-(1->2)-O-β-D-glucopyranoside

Conditions
ConditionsYield
With sodium hydroxide at 25℃; for 6h;A 64%
B n/a
(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
methyl 3-methoxybenzoate
5368-81-0

methyl 3-methoxybenzoate

A

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

4-hydroxy-3-methoxybenzoic acid methyl ester

B

3-methoxymethylsalicylate
6342-70-7

3-methoxymethylsalicylate

C

methyl 5-methoxy-2-hydroxybenzoate
2905-82-0

methyl 5-methoxy-2-hydroxybenzoate

Conditions
ConditionsYield
Stage #1: methyl 3-methoxybenzoate With 6,7-dichlorobenzo[d][1,2]dioxine-1,4-dione In chloroform at 50℃; for 24h;
Stage #2: With water; sodium hydrogencarbonate In methanol at 50℃; for 1h; Inert atmosphere; Overall yield = 55 %; regioselective reaction;
A 20%
B 18%
C 17%
3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

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

4-hydroxy-3-methoxybenzoic acid methyl ester

methanol
67-56-1

methanol

2-methoxy-4-propenylphenol
97-54-1

2-methoxy-4-propenylphenol

acetic anhydride
108-24-7

acetic anhydride

A

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

4-hydroxy-3-methoxybenzoic acid methyl ester

B

Acetic acid 2-methoxy-4-[1-methoxy-2-(2-methoxy-4-propyl-phenoxy)-propyl]-phenyl ester
36831-66-0

Acetic acid 2-methoxy-4-[1-methoxy-2-(2-methoxy-4-propyl-phenoxy)-propyl]-phenyl ester

(E)-1-<(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-1-benzofuran-5-yl>-1-propene
2680-81-1, 23518-29-8, 23518-30-1, 51020-86-1, 64870-40-2, 69744-09-8, 72274-58-9, 72274-59-0, 83377-50-8, 88034-58-6, 127000-67-3

(E)-1-<(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-1-benzofuran-5-yl>-1-propene

D

vanillin
121-33-5

vanillin

Acetic acid 4-(2-hydroperoxy-1-methoxy-propyl)-2-methoxy-phenyl ester
138252-48-9

Acetic acid 4-(2-hydroperoxy-1-methoxy-propyl)-2-methoxy-phenyl ester

Acetic acid 4-(2-acetylperoxy-1-methoxy-propyl)-2-methoxy-phenyl ester
138252-52-5

Acetic acid 4-(2-acetylperoxy-1-methoxy-propyl)-2-methoxy-phenyl ester

Conditions
ConditionsYield
With pyridine; oxygen Mechanism; Product distribution; 1.) 10 -15 deg C, 5 d, methylene blue, irradiation, 2.) r.t., overnight; also with ethanol;
methyl 1-(3-bromopropyl)-3-methoxy-4-ketocyclohexa-2,5-diene-1-carboxylate
103669-14-3

methyl 1-(3-bromopropyl)-3-methoxy-4-ketocyclohexa-2,5-diene-1-carboxylate

A

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

4-hydroxy-3-methoxybenzoic acid methyl ester

methyl <3aα,7β,7aα>-6-keto-7-methoxy-1,2,3,6,7,7a-hexahydro-3aH-indene-3a-carboxylate

methyl <3aα,7β,7aα>-6-keto-7-methoxy-1,2,3,6,7,7a-hexahydro-3aH-indene-3a-carboxylate

methyl <3aα,7aα>-6-keto-5-methoxy-1,2,3,6,7,7a-hexahydro-3aH-indene-3a-carboxylate

methyl <3aα,7aα>-6-keto-5-methoxy-1,2,3,6,7,7a-hexahydro-3aH-indene-3a-carboxylate

Conditions
ConditionsYield
With tri-n-butyl-tin hydride In benzene Heating; Yields of byproduct given;
With tri-n-butyl-tin hydride In benzene Heating; Yield given;
Methyl ferulate
2309-07-1

Methyl ferulate

A

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

4-hydroxy-3-methoxybenzoic acid methyl ester

B

vanillin
121-33-5

vanillin

Conditions
ConditionsYield
With oxygen; salcomine In chloroform at 25℃; under 7500.6 Torr; for 48h; Product distribution; Mechanism; different phenols, solvents and reaction times;A 61 % Chromat.
B 39 % Chromat.
With oxygen; [N,N'-bis(salicylidene)ethane-1,2-diaminato]cobalt(II) In chloroform at 24.84℃; under 7500.75 Torr; for 48h; Product distribution;
hydrogenchloride
7647-01-0

hydrogenchloride

methanol
67-56-1

methanol

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

3-methoxy-4-hydroxybenzoic acid

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

4-hydroxy-3-methoxybenzoic acid methyl ester

methyl (E)-[(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-1-benzofuran-5-yl]propenoate

methyl (E)-[(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-1-benzofuran-5-yl]propenoate

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

7-Methoxy-5-((E)-2-methoxycarbonyl-vinyl)-benzofuran-3-carboxylic acid methyl ester

7-Methoxy-5-((E)-2-methoxycarbonyl-vinyl)-benzofuran-3-carboxylic acid methyl ester

D

(E)-3-Hydroxy-2-[2-hydroxy-3-methoxy-5-((E)-2-methoxycarbonyl-vinyl)-phenyl]-3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid methyl ester

(E)-3-Hydroxy-2-[2-hydroxy-3-methoxy-5-((E)-2-methoxycarbonyl-vinyl)-phenyl]-3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid methyl ester

Conditions
ConditionsYield
With oxygen; [N,N'-bis(salicylidene)ethane-1,2-diaminato]cobalt(II) In chloroform at 24.84℃; under 7500.75 Torr; for 48h; Product distribution;
methyl 3,4-dimethoxybenzoate
2150-38-1

methyl 3,4-dimethoxybenzoate

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

4-hydroxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diluted NaOH-solution
2: diluted hydrochloric acid / 160 - 170 °C / im geschlossenen Rohr
3: HCl
View Scheme
Veratric acid
93-07-2

Veratric acid

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

4-hydroxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diluted hydrochloric acid / 160 - 170 °C / im geschlossenen Rohr
2: HCl
View Scheme
3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

A

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

4-hydroxy-3-methoxybenzoic acid methyl ester

B

3-hydroxy-4-methoxybenzoate
6702-50-7

3-hydroxy-4-methoxybenzoate

methanol
67-56-1

methanol

2-(4-hydroxy-3-methoxyphenyl)-2-methoxyacetonitrile
1000180-41-5

2-(4-hydroxy-3-methoxyphenyl)-2-methoxyacetonitrile

A

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

4-hydroxy-3-methoxybenzoic acid methyl ester

B

C11H13NO4
1000180-45-9

C11H13NO4

Conditions
ConditionsYield
With manganese(IV) oxide; water for 24h; Title compound not separated from byproducts.;
2-(4-hydroxy-3-methoxyphenyl)-2-methoxyacetonitrile
1000180-41-5

2-(4-hydroxy-3-methoxyphenyl)-2-methoxyacetonitrile

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

4-hydroxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
With manganese(IV) oxide; acetic acid In methanol; water for 24h;
methanol
67-56-1

methanol

lignin

lignin

A

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

4-hydroxy-3-methoxybenzoic acid methyl ester

B

methyl syringate
884-35-5

methyl syringate

C

vanillin
121-33-5

vanillin

D

syringic aldehyde
134-96-3

syringic aldehyde

Conditions
ConditionsYield
With oxygen; phosphomolybdic acid In water at 170℃; under 3825.38 Torr;
methanol
67-56-1

methanol

lignin

lignin

A

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

4-hydroxy-3-methoxybenzoic acid methyl ester

B

vanillin
121-33-5

vanillin

Conditions
ConditionsYield
With oxygen; phosphomolybdic acid In water at 170℃; under 3825.38 Torr;
methanol
67-56-1

methanol

lignin

lignin

A

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

4-hydroxy-3-methoxybenzoic acid methyl ester

B

2,4'-dihydroxy-3'-methoxyacetophenone
18256-48-9

2,4'-dihydroxy-3'-methoxyacetophenone

C

vanillin
121-33-5

vanillin

Conditions
ConditionsYield
phosphomolybdic acid In water at 170℃; under 7500.75 Torr; Inert atmosphere;
vanillin
121-33-5

vanillin

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

4-hydroxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: silver(l) oxide; sodium hydroxide / water / 3 h / 80 °C
2: sulfuric acid / 2.5 h / 100 °C / Autoclave
View Scheme
Multi-step reaction with 2 steps
1: recombinant aldehyde dehydrogenase from bovine lens; 1,4-dithio-D,L-threitol; water‐forming NADH oxidase from Streptococcus mutans; NAD / aq. phosphate buffer / 24 h / 40 °C / pH 8.5 / Green chemistry; Enzymatic reaction
2: methanol; ethyl acetate / 1 h / 30 °C
View Scheme
3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

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

4-hydroxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
In methanol; ethyl acetate at 30℃; for 1h;
methanol
67-56-1

methanol

guaiacylglycerol-β-guaiacyl ether
7382-59-4

guaiacylglycerol-β-guaiacyl ether

A

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

4-hydroxy-3-methoxybenzoic acid methyl ester

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With oxygen; sodium hydroxide at 200℃; under 7500.75 Torr; for 10h; Catalytic behavior; Reagent/catalyst; Pressure; Temperature; Autoclave;A 23 %Chromat.
B 31 %Chromat.
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

allyl bromide
106-95-6

allyl bromide

methyl 3-methoxy-4-(2-propenoxy)benzoate
171002-53-2

methyl 3-methoxy-4-(2-propenoxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In acetone at 40℃; for 16h; Inert atmosphere;100%
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 2h;95%
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Metallation;
Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 18h; Alkylation;
92%
With sodium hydride 1.) DMF, r.t., 2 h; 2.) r.t., 24 h; Multistep reaction;
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

3-methoxy-4-trifluoromethane-sulfonyloxy-benzoic acid methyl ester
175153-75-0

3-methoxy-4-trifluoromethane-sulfonyloxy-benzoic acid methyl ester

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine In dichloromethane at -78 - 20℃; for 4h;100%
With pyridine In dichloromethane at 0℃; for 0.333333h;100%
With pyridine In dichloromethane at 0℃; for 4h;99%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

benzyl bromide
100-39-0

benzyl bromide

methyl 4-(benzyloxy)-3-methoxybenzoate
56441-97-5

methyl 4-(benzyloxy)-3-methoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;100%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;100%
With potassium carbonate In N,N-dimethyl-formamide at 100℃;100%
1,5-dibromo-pentane
111-24-0

1,5-dibromo-pentane

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

4-hydroxy-3-methoxybenzoic acid methyl ester

1',5'-bis<2-methoxy-(4-methoxycarbonyl)phenoxy>pentane
145325-42-4

1',5'-bis<2-methoxy-(4-methoxycarbonyl)phenoxy>pentane

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 3h; Inert atmosphere;100%
With potassium carbonate In N,N-dimethyl-formamide for 3h; Inert atmosphere;7.92 g
2-(prop-2-yn-1-yl)propane-1,3-diol
771430-70-7

2-(prop-2-yn-1-yl)propane-1,3-diol

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

4-hydroxy-3-methoxybenzoic acid methyl ester

4,4'-((2-(prop-2-yn-1-yl)propane-1,3-diyl)bis(oxy))bis(3-methoxybenzoic acid methyl ester)

4,4'-((2-(prop-2-yn-1-yl)propane-1,3-diyl)bis(oxy))bis(3-methoxybenzoic acid methyl ester)

Conditions
ConditionsYield
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 0.583333h; Inert atmosphere;
Stage #2: 2-(prop-2-yn-1-yl)propane-1,3-diol In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
100%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

methyl 4-(3-chloropropoxy)-3-methoxybenzoate
111627-40-8

methyl 4-(3-chloropropoxy)-3-methoxybenzoate

Conditions
ConditionsYield
With potassium carbonate; sodium chloride In acetone at 55 - 60℃; for 5h; Heating / reflux;99.5%
With potassium carbonate In acetone; acetonitrile at 75 - 79℃; for 5h; Heating / reflux;99.3%
With potassium chloride; potassium carbonate In acetone at 55 - 60℃; for 10h; Heating / reflux;98.2%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

2,3,4,6-tetra-O-acetyl-D-allopyranosyl N-phenyltrifluoroacetimidate
1293384-39-0

2,3,4,6-tetra-O-acetyl-D-allopyranosyl N-phenyltrifluoroacetimidate

methyl 3-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-allopyranosyloxy)benzoate
1293384-41-4

methyl 3-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-allopyranosyloxy)benzoate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 2h; Molecular sieve;99%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

1-Bromodocosane
6938-66-5

1-Bromodocosane

C31H54O4

C31H54O4

Conditions
ConditionsYield
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With potassium carbonate at 80℃; for 0.5h;
Stage #2: 1-Bromodocosane at 70℃; for 15h;
99%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

4-bromobutyric acid allyl ester
178215-45-7

4-bromobutyric acid allyl ester

C16H20O6

C16H20O6

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃; for 1.5h;99%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

benzyl chloride
100-44-7

benzyl chloride

methyl 4-(benzyloxy)-3-methoxybenzoate
56441-97-5

methyl 4-(benzyloxy)-3-methoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;98%
With potassium carbonate In acetonitrile at 90℃; for 2h; Inert atmosphere;97%
With potassium carbonate In acetonitrile at 20℃; for 8h; Inert atmosphere;81%
With potassium carbonate; potassium iodide In acetone Inert atmosphere; Reflux;57%
With potassium hydroxide
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

propargyl bromide
106-96-7

propargyl bromide

3-methoxy-4-(prop-2-yn-1-yloxy)benzoic acid methyl ester

3-methoxy-4-(prop-2-yn-1-yloxy)benzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 3h; Ambient temperature;98%
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With potassium carbonate In N,N-dimethyl-formamide for 0.5h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 25℃; for 2h;
95%
With potassium carbonate In N,N-dimethyl-formamide93%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

methanol
67-56-1

methanol

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

4-hydroxy-3-methoxybenzoic acid methyl ester

methyl (1R*,2R*,6R*,7R*)-11,11-dimethoxy-3-oxa-10-oxotricyclo[5.2.2.02,6]undec-8-en-8-carboxylate

methyl (1R*,2R*,6R*,7R*)-11,11-dimethoxy-3-oxa-10-oxotricyclo[5.2.2.02,6]undec-8-en-8-carboxylate

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene at 50℃; for 1h; Diels-Alder reaction;98%
With [bis(acetoxy)iodo]benzene at 50℃; for 1h; Oxidation; Diels-Alder cycloaddition;88%
methanol
67-56-1

methanol

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

4-hydroxy-3-methoxybenzoic acid methyl ester

benzyl vinyl ether
935-04-6

benzyl vinyl ether

methyl (1S*,4S*,7S*)-7-(benzyloxy)-3,3-dimethoxy-2-oxobicyclo[2.2.2]oct-5-en-5-carboxylate

methyl (1S*,4S*,7S*)-7-(benzyloxy)-3,3-dimethoxy-2-oxobicyclo[2.2.2]oct-5-en-5-carboxylate

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene at 0℃; for 1h; Product distribution; Further Variations:; Temperatures; Diels-Alder reaction;98%
With [bis(acetoxy)iodo]benzene at 50℃; for 1h; Diels-Alder reaction;98%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

ethyl iodide
75-03-6

ethyl iodide

4-ethoxy-3-methoxybenzoic acid methyl ester
3535-24-8

4-ethoxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃;98%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h; Alkylation;82%
With potassium carbonate In N,N-dimethyl-formamide
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

1-iodo-propane
107-08-4

1-iodo-propane

methyl 3-methoxy-4-propoxybenzoate
3535-26-0

methyl 3-methoxy-4-propoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃;98%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

Dibenzyl N,N-diisopropylphosphoramidite
108549-23-1

Dibenzyl N,N-diisopropylphosphoramidite

methyl 4-((bis(benzyloxy)phosphoryl)oxy)-3-methoxybenzoate

methyl 4-((bis(benzyloxy)phosphoryl)oxy)-3-methoxybenzoate

Conditions
ConditionsYield
With 1H-tetrazole; dihydrogen peroxide In dichloromethane; water at 0 - 20℃; for 1h;98%
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole In dichloromethane; acetonitrile at 20℃; for 8h;
Stage #2: With dihydrogen peroxide In dichloromethane; acetonitrile at 20℃; for 2h;
97%
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole In dichloromethane; acetonitrile at 20℃; for 8h;
Stage #2: With dihydrogen peroxide In dichloromethane; acetonitrile at 0 - 20℃; for 2h;
97%
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole In dichloromethane; acetonitrile at 20℃; for 8h;
Stage #2: With dihydrogen peroxide In dichloromethane; acetonitrile at 0 - 20℃; for 2h;
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

1-Bromo-2-chloroethane
107-04-0

1-Bromo-2-chloroethane

4-(2-Chloro-ethoxy)-5-methoxy-benzoic acid methyl ester
214470-56-1

4-(2-Chloro-ethoxy)-5-methoxy-benzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80 - 85℃; for 8h; Heating / reflux;97.8%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 3h;97%
ethyl bromide
74-96-4

ethyl bromide

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

4-hydroxy-3-methoxybenzoic acid methyl ester

4-ethoxy-3-methoxybenzoic acid methyl ester
3535-24-8

4-ethoxy-3-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 2h;97%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

4-bromo-2-fluorobenzyl bromide
76283-09-5

4-bromo-2-fluorobenzyl bromide

4-(4-bromo-2-fluoro-benzyloxy)-3-methoxy-benzoic acid methyl ester

4-(4-bromo-2-fluoro-benzyloxy)-3-methoxy-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 4-bromo-2-fluorobenzyl bromide In N,N-dimethyl-formamide at 20℃;
96%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

1-chloro-2-(2-methoxyethoxy)ethane
52808-36-3

1-chloro-2-(2-methoxyethoxy)ethane

3-methoxy-4-[2-(2-methoxyethoxy)ethoxy]benzoic acid methyl ester
857934-56-6

3-methoxy-4-[2-(2-methoxyethoxy)ethoxy]benzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 24h;96%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

2-Fluoroaniline
348-54-9

2-Fluoroaniline

methyl 4-((2-fluorophenyl)amino)-3-methoxybenzoate

methyl 4-((2-fluorophenyl)amino)-3-methoxybenzoate

Conditions
ConditionsYield
With potassium phosphate; trifluoromethylsulfonic anhydride; methanesulfonato(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II) In water; toluene at 120℃; Flow reactor;96%
methanol
67-56-1

methanol

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

4-hydroxy-3-methoxybenzoic acid methyl ester

methyl vinyl ketone
78-94-4

methyl vinyl ketone

C14H18O6

C14H18O6

Conditions
ConditionsYield
Stage #1: methanol; 4-hydroxy-3-methoxybenzoic acid methyl ester With iodobenzene; 3-chloro-benzenecarboperoxoic acid
Stage #2: methyl vinyl ketone In methanol at 20℃; for 0.5h; Diels-Alder Cycloaddition;
96%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

cyclopentyl iodide
1556-18-9

cyclopentyl iodide

methyl-3-methoxy-4-cyclopentyl-oxybenzoate

methyl-3-methoxy-4-cyclopentyl-oxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃;96%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

tert-butyl N-(2-chloroethyl)carbamate
71999-74-1

tert-butyl N-(2-chloroethyl)carbamate

methyl 4-{2-[(tert-butoxycarbonyl)amino]ethoxy}-3-methoxybenzoate
1569084-51-0

methyl 4-{2-[(tert-butoxycarbonyl)amino]ethoxy}-3-methoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;96%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

cyclopropylmethyl halide

cyclopropylmethyl halide

methyl 4-(cyclopropylmethoxy)-3-methoxybenzoate
1040724-12-6

methyl 4-(cyclopropylmethoxy)-3-methoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 170℃; for 1h; Microwave irradiation; Sealed tube;96%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

4-(4-bromo-benzyloxy)-3-methoxy-benzoic acid methyl ester

4-(4-bromo-benzyloxy)-3-methoxy-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 1-bromomethyl-4-bromobenzene In N,N-dimethyl-formamide at 20℃;
95%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

1-chloro-3,6,9-trioxadecane
52995-76-3

1-chloro-3,6,9-trioxadecane

3-methoxy-4-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}benzoic acid methyl ester
857934-57-7

3-methoxy-4-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}benzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 24h;95%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

2-(trifluoromethoxy)ethyl trifluoromethanesulphonate
329710-76-1

2-(trifluoromethoxy)ethyl trifluoromethanesulphonate

methyl 3-methoxy-4-(2-(trifluoromethoxy)ethoxy)benzoate
1346498-24-5

methyl 3-methoxy-4-(2-(trifluoromethoxy)ethoxy)benzoate

Conditions
ConditionsYield
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.666667h; Inert atmosphere;
Stage #2: 2-(trifluoromethoxy)ethyl trifluoromethanesulphonate In N,N-dimethyl-formamide; mineral oil at 0 - 40℃; for 0.666667h;
95%
Stage #1: 4-hydroxy-3-methoxybenzoic acid methyl ester With sodium hydride In N,N-dimethyl-formamide Inert atmosphere;
Stage #2: 2-(trifluoromethoxy)ethyl trifluoromethanesulphonate In N,N-dimethyl-formamide at 20 - 50℃; for 4h;

3943-74-6Relevant articles and documents

Hydroquinone glycosides from leaves of Myrsine seguinii

Zhong, Xi-Ning,Otsuka, Hideaki,Ide, Toshinori,Hirata, Eiji,Takushi, Anki,Takeda, Yoshio

, p. 2149 - 2153 (1998)

From leaves of Myrsine seguinii, seven hydroquinone glycosides were isolated. By spectroscopic analyses, their structures were elucidated to be arbutin, arbutin 2'- and 6'-O-β-apiofuranosides (seguinosides A and B, respectively), and the benzoyl, p-hydroxybenzoyl, 3-methoxy-4-hydroxybenzoyl and 3,5-dimethoxy-4-hydroxybenzoyl esters of the alcohol hydroxyl group on C- 5'' of arbutin 2'-O-β-apiofuranoside (seguinosides C-F, respectively).

Diploquinones A and B, Two New Phytotoxic Tetrasubstituted 1,4-Naphthoquinones from Diplodia mutila, a Causal Agent of Grapevine Trunk Disease

Reveglia, Pierluigi,Savocchia, Sandra,Billones-Baaijens, Regina,Masi, Marco,Cimmino, Alessio,Evidente, Antonio

, p. 11968 - 11973 (2018)

Two new phytotoxic tetrasubstituted 1,4-naphthoquinones, named diploquinones A and B, were isolated together with vanillic acid from Diplodia mutila (DAR78993), a grapevine pathogen involved in Botryosphaeria dieback in Australia. Diploquinones A and B were characterized as 6,7-dihydroxy-2-methoxy-5-methylnaphthalene-1,4-dione and 3,5,7-trihydroxy-2-methoxynaphthalene-1,4-dione using spectroscopic methods (essentially 1D and 2D 1H and 13C NMR and HR ESIMS). The already known vanillic acid was isolated for the first time as fungal phytotoxin and as metabolite of D. mutila. The three compounds were assayed on detached grapevine leaves (Vitis vinifera cv. Shiraz) at concentrations of 10-3 M and 2.5 × 10-3 M. Vanillic acid showed the highest phytotoxic effect on grapevine leaves irrespective of the tested concentration, while diploquinones A and B showed varying degrees of toxicity.

COMPOSITIONS AND METHODS RELATED TO MOLECULAR CONJUGATION

-

Page/Page column 80; 81, (2021/06/11)

The invention relates to activated Michael acceptor (AMA) compounds that can undergo conjugation with biomolecules containing Michael donor moieties, thereby providing plasma-stable antibody-drug conjugates (ADCs). Pharmaceutical compositions of the ADCs are disclosed as well. Also provided herein are a number of applications (e.g., therapeutic applications) in which the compositions are useful.

Novel 4-Anilinoquinazoline Derivatives as Potent Anticancer Agents: Design, Synthesis, Cytotoxic Activity, and Docking Study

Dabirian, Sara,Dogaheh, Mahtab Ghasemi,Ghasemi, Saeed,Moghadam, Fatemeh Azmian,Mojabi, Mohammad,Yousefbeyk, Fatemeh

, p. 730 - 739 (2021/10/29)

The simultaneous inhibition of EGFR and VEGFR-2 is a promising method in cancer treatment. In the present work, several 4-Anilinoquinazoline derivatives encompassing different substitutions at the C-4 and C-7 positions of a quinazoline core were designed, synthesised, and evaluated for their cytotoxicity on A431, HUVEC, and HU02 cell lines. Docking studies were carried out to test the interactions of all synthesised compounds with EGFR and VEGFR-2. Furthermore, a wound healing assay was done for the investigation of cell migration. The most potent compound was 8l followed by the compounds 8i and 8j which showed better cytotoxic activities on A431 and HUVEC cell lines than the standard (Vandetanib). The compounds 8f and 8a represented the best docking energies of 8.99 and 9.35 kcal mol-1 for EGFR and VEGFR, respectively. Moreover, molecular docking studies exhibited that compound 8l showed efficient binding affinity against both EGFR and VEGFR-2. It can bind to these receptors through the formation of essential hydrogen bonds between the quinazoline N1 atom and the Met796 backbone of EGFR and two hydrogen bonds with Cys919 and Thr916 of VEGFR-2 with energies of-7.99 and-7.85 kcal mol-1, respectively. In addition, this compound displayed the highest activity on cell migration and wound healing. Compound 8l with the highest cytotoxic activity can be considered a candidate for further investigation and structural optimisation as an antiproliferative agent.

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