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2309-07-1

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2309-07-1 Usage

Uses

Different sources of media describe the Uses of 2309-07-1 differently. You can refer to the following data:
1. Ferulic acid is a hydroxycinnamic acid that is abundant in plants and originally derived from giant fennel (F. communis). This naturally-occurring phenolic has antioxidant activities that provide protection against inflammation and cancer. Ferulic acid methyl ester is a lipophilic derivative of ferulic acid, demonstrating increased ability to cross cell membranes. Ferulic acid methyl ester has less antioxidant capacity than ferulic acid in neuronal PC12 cells (IC50 = 74.7 μM for ferulic acid ethyl ester vs. 44.6 μM for ferulic acid, 2,2-diphenyl-1-picrylhydrazyl radical scavenging). Ferulic acid methyl ester, at 10-25 μg/ml, inhibits the release of pro-inflammatory cytokines, blocks the expression of COX-2, and reduces nitric oxide generation from LPS-stimulated macrophages.
2. Ferulic Acid Methyl Ester is a derivative of Ferulic Acid (F308900), used as an antioxidant and food preservative. It has less antioxidant capacity than ferulic acid.

Definition

ChEBI: A cinnamate ester that is the methyl ester of ferulic acid. It has been isolated from Pisonia aculeata.

Check Digit Verification of cas no

The CAS Registry Mumber 2309-07-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,0 and 9 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2309-07:
(6*2)+(5*3)+(4*0)+(3*9)+(2*0)+(1*7)=61
61 % 10 = 1
So 2309-07-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3/b6-4+

2309-07-1 Well-known Company Product Price

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  • Alfa Aesar

  • (B22657)  Methyl 4-hydroxy-3-methoxycinnamate, 99%   

  • 2309-07-1

  • 2g

  • 464.0CNY

  • Detail
  • Alfa Aesar

  • (B22657)  Methyl 4-hydroxy-3-methoxycinnamate, 99%   

  • 2309-07-1

  • 10g

  • 1487.0CNY

  • Detail

2309-07-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name trans-methylferulate

1.2 Other means of identification

Product number -
Other names Methyl 4-hydroxy-3-methoxycinnamate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:2309-07-1 SDS

2309-07-1Synthetic route

methanol
67-56-1

methanol

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

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

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With Dowex 50 W x 8200-400 Heating;100%
With thionyl chloride Ambient temperature;100%
With sulfuric acid at 0℃; for 12h; Darkness; Reflux;99%
methyl (E)-4-methoxymethyl-3-methoxycinnamate
220300-07-2

methyl (E)-4-methoxymethyl-3-methoxycinnamate

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.5h; Heating;100%
vanillin
121-33-5

vanillin

methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
In water at 90℃; for 0.5h; Horner-Wadsworth-Emmons Olefination; Green chemistry;99%
In toluene at 150℃; for 0.166667h; Wittig Olefination; Inert atmosphere; Microwave irradiation; Sealed tube; stereoselective reaction;98%
In toluene at 150℃; for 0.166667h; Sealed tube; Microwave irradiation;98%
methanol
67-56-1

methanol

[(E)-3-(4-Hydroxy-3-methoxy-phenyl)-acryloyloxymethylene]-dimethyl-ammonium; chloride
92446-10-1

[(E)-3-(4-Hydroxy-3-methoxy-phenyl)-acryloyloxymethylene]-dimethyl-ammonium; chloride

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
98%
methanol
67-56-1

methanol

3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

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

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With sulfuric acid for 4h; Reflux;96%
With sulfuric acid Fischer-Speier Esterification; Sealed tube; Heating; Microwave irradiation;
3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyldiazonium tetrafluoroborate

3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyldiazonium tetrafluoroborate

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With palladium diacetate In methanol at 20℃; Heck Reaction;96%
(E)-methyl 3-(4-(((2'-cyanobiphenyl-4-yl)methyl)diisopropylsilyloxy)-3-methoxyphenyl)acrylate

(E)-methyl 3-(4-(((2'-cyanobiphenyl-4-yl)methyl)diisopropylsilyloxy)-3-methoxyphenyl)acrylate

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;94%
methyl (E)-3-(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)acrylate
259267-38-4

methyl (E)-3-(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)acrylate

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 2h;90%
2-methoxy-4-propenylphenol
97-54-1

2-methoxy-4-propenylphenol

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With Hoveyda-Grubbs catalyst first generation In 1,2-dichloro-ethane at 70℃; Cross Metathesis; Schlenk technique; Inert atmosphere; Glovebox;90%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

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

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With sulfuric acid In methanol at 20℃; for 4h;84%
Multi-step reaction with 2 steps
2: 98 percent
View Scheme
With sulfuric acid In methanol; ice-water; diethyl ether; dichloromethane
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetonitrile / 18 h / 70 °C / Inert atmosphere
1.2: 24 h / 660 °C / Inert atmosphere
2.1: methanol / 18 h / 20 °C / Inert atmosphere
3.1: bis-triphenylphosphine-palladium(II) chloride; ammonium formate / acetonitrile / 24 h / 80 °C / Inert atmosphere
View Scheme
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

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

dimethyl sulfate
77-78-1

dimethyl sulfate

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With potassium hydrogencarbonate In acetone at 20℃; for 1.5h;84%
(E)-methyl 3-(4-(allyloxy)-3-methoxyphenyl)acrylate

(E)-methyl 3-(4-(allyloxy)-3-methoxyphenyl)acrylate

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; ammonium formate In acetonitrile at 80℃; for 24h; Inert atmosphere;71%
methanol
67-56-1

methanol

3-O-(6-O-trans-ferulyl-β-glucopyranoside)-5-O-(6-O-malonyl-β-glucopyranoside) cyanidin

3-O-(6-O-trans-ferulyl-β-glucopyranoside)-5-O-(6-O-malonyl-β-glucopyranoside) cyanidin

A

3,5-di-O-β-D-glucopyranoside of cyanidin
20905-74-2

3,5-di-O-β-D-glucopyranoside of cyanidin

B

cyanidin-3-glucoside
47705-70-4, 142506-26-1

cyanidin-3-glucoside

C

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With hydrogenchloride at 65℃; for 4h;A n/a
B n/a
C 70%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

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

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
In diethyl ether at 0℃; for 2h;69%
With methanol
In diethyl ether Esterification;
In methanol at 20℃; for 4h; Methylation;
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

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

choline chloride
67-48-1

choline chloride

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With urea at 140℃; for 2h; Green chemistry;55%
methanol
67-56-1

methanol

4-acetoxy-3-methoxycinnamoyl chloride
50906-12-2

4-acetoxy-3-methoxycinnamoyl chloride

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With pyridine
Conditions
ConditionsYield
With sodium methylate for 1h; Ambient temperature;
methanol
67-56-1

methanol

cistanoside D
94492-21-4

cistanoside D

A

homovanillyl alcohol
2380-78-1

homovanillyl alcohol

B

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With acetyl chloride for 0.5h; Heating;
methanol
67-56-1

methanol

(E)-3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid 2-hydroxy-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester
120601-65-2, 120665-05-6

(E)-3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid 2-hydroxy-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester

A

1-O-β-D-glucopyranosyl-sn-glycerol
23202-73-5

1-O-β-D-glucopyranosyl-sn-glycerol

B

Methyl ferulate
2309-07-1

Methyl ferulate

C

3-O-β-D-glucopyranosyl-sn-glycerol
23202-75-7

3-O-β-D-glucopyranosyl-sn-glycerol

Conditions
ConditionsYield
With sodium methylate
sodium methylate
124-41-4

sodium methylate

6'-O-trans-feruloylnodakenin
131623-14-8

6'-O-trans-feruloylnodakenin

A

Methyl ferulate
2309-07-1

Methyl ferulate

B

1'-O-β-D-glucopyranosyl-(2R)-marmesin
495-30-7, 495-31-8

1'-O-β-D-glucopyranosyl-(2R)-marmesin

Conditions
ConditionsYield
In methanol for 8h; Ambient temperature;
sodium methylate
124-41-4

sodium methylate

(+)-catechin 5-O-β-D-(2''-O-feruloyl-6''-O-p-coumaroyl)-glucopyranoside
103215-60-7

(+)-catechin 5-O-β-D-(2''-O-feruloyl-6''-O-p-coumaroyl)-glucopyranoside

A

methyl 4-hydroxycinnamate
3943-97-3

methyl 4-hydroxycinnamate

B

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
In methanol for 0.166667h; Product distribution; Heating;
Conditions
ConditionsYield
With sodium methylate In methanol for 1h; Ambient temperature;
6'-trans feruloyl lyaloside
83404-71-1

6'-trans feruloyl lyaloside

A

Methyl ferulate
2309-07-1

Methyl ferulate

B

lyaloside
56021-85-3

lyaloside

Conditions
ConditionsYield
With potassium methanolate In methanol for 48h;
3-O-(6-O-ferulyl-2-O-(2-O-sinapyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidin

3-O-(6-O-ferulyl-2-O-(2-O-sinapyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidin

A

methyl (E)-sinapate
42041-51-0

methyl (E)-sinapate

B

Methyl ferulate
2309-07-1

Methyl ferulate

C

3-O-(2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidin

3-O-(2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidin

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 0℃;
Rhynchophine
84638-29-9

Rhynchophine

A

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With sodium methylate In methanolA 4 mg
B 3 mg
4-O-β-D-glucopyranosyl-(E)-ferulic acid methyl ester
94393-06-3

4-O-β-D-glucopyranosyl-(E)-ferulic acid methyl ester

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With sulfuric acid In ethanol for 2h;
(E)-3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid 2-hydroxy-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester
120601-65-2, 120665-05-6

(E)-3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid 2-hydroxy-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester

A

1-O-β-D-glucopyranosyl-sn-glycerol
23202-73-5

1-O-β-D-glucopyranosyl-sn-glycerol

B

Methyl ferulate
2309-07-1

Methyl ferulate

C

3-O-β-D-glucopyranosyl-sn-glycerol
23202-75-7

3-O-β-D-glucopyranosyl-sn-glycerol

Conditions
ConditionsYield
With sodium methylate In methanol
acuminatuside

acuminatuside

A

Methyl ferulate
2309-07-1

Methyl ferulate

B

aucubin
479-98-1

aucubin

Conditions
ConditionsYield
With sodium methylate In methanol at 22℃; for 1h;
methanol
67-56-1

methanol

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

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

A

Methyl ferulate
2309-07-1

Methyl ferulate

B

methyl (Z)-3-(4-hydroxy-3-methoxyphenyl)acrylate
34298-89-0

methyl (Z)-3-(4-hydroxy-3-methoxyphenyl)acrylate

Methyl <5-hydroxy-t-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-c-2-(methoxycarbonyl)-r-1-indanyl>acetate
144878-42-2

Methyl <5-hydroxy-t-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-c-2-(methoxycarbonyl)-r-1-indanyl>acetate

(1R,2S,3S)-5-Hydroxy-3-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-1-methyl-indan-2-carboxylic acid methyl ester

(1R,2S,3S)-5-Hydroxy-3-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-1-methyl-indan-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 6h; Heating; Further byproducts given;A 1.5 g
B 100 mg
C 7.09 g
D 280 mg
Methyl ferulate
2309-07-1

Methyl ferulate

acetic anhydride
108-24-7

acetic anhydride

(E)-methyl 3-(4-acetoxy-3-methoxyphenyl)acrylate
144256-14-4

(E)-methyl 3-(4-acetoxy-3-methoxyphenyl)acrylate

Conditions
ConditionsYield
With pyridine100%
With pyridine In ethyl acetate at 20℃;91%
With triethylamine In dichloromethane at 20℃; for 4h;85%
Methyl ferulate
2309-07-1

Methyl ferulate

methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate
56024-44-3

methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In methanol100%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 12h;98%
With hydrogen; palladium 10% on activated carbon In methanol at 10 - 35℃; for 4h;97%
Methyl ferulate
2309-07-1

Methyl ferulate

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

methyl (2E)-3-[4-[[tert-butyldimethylsilyl]oxy]-3-methoxyphenyl]-prop-2-enoate
925439-02-7

methyl (2E)-3-[4-[[tert-butyldimethylsilyl]oxy]-3-methoxyphenyl]-prop-2-enoate

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 2h;99%
Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene98%
With diisobutylaluminium hydride In dichloromethane at -78 - 20℃; for 1h; Inert atmosphere; stereoselective reaction;92%
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 12h;87%
Methyl ferulate
2309-07-1

Methyl ferulate

benzyl bromide
100-39-0

benzyl bromide

(E)-3-(3-methoxy-4-(benzyloxy)phenyl)methyl acrylate
93878-20-7

(E)-3-(3-methoxy-4-(benzyloxy)phenyl)methyl acrylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2h;98%
With 18-crown-6 ether; potassium carbonate In toluene Heating;92%
With potassium carbonate In acetone for 10h; Reflux; Inert atmosphere;92.5%
Methyl ferulate
2309-07-1

Methyl ferulate

benzyl chloride
100-44-7

benzyl chloride

(E)-3-(3-methoxy-4-(benzyloxy)phenyl)methyl acrylate
93878-20-7

(E)-3-(3-methoxy-4-(benzyloxy)phenyl)methyl acrylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 6h;96.1%
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 3h; Alkylation;
Methyl ferulate
2309-07-1

Methyl ferulate

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

methyl 3-[2-methoxy-4-(methoxycarbonylmethoxy)phenyl]acrylate
203726-34-5

methyl 3-[2-methoxy-4-(methoxycarbonylmethoxy)phenyl]acrylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Alkylation;94%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Methyl ferulate
2309-07-1

Methyl ferulate

(2E)-3-[3-methox-4-[[(trifluormethyl)sulfonyl]oxy]phenyl]methyl ester

(2E)-3-[3-methox-4-[[(trifluormethyl)sulfonyl]oxy]phenyl]methyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 24h; Inert atmosphere;91%
Methyl ferulate
2309-07-1

Methyl ferulate

propargyl bromide
106-96-7

propargyl bromide

methyl (E)-3-(3-methoxy-4-prop-2-ynoxyphenyl)prop-2-enoate

methyl (E)-3-(3-methoxy-4-prop-2-ynoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
Stage #1: Methyl ferulate With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 23h; Inert atmosphere;
91%
Methyl ferulate
2309-07-1

Methyl ferulate

methyl (E)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-(3-methoxy-3-oxoprop-1-enyl)-2,3-dihydrobenzofuran-3-carboxylate
918446-05-6

methyl (E)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-(3-methoxy-3-oxoprop-1-enyl)-2,3-dihydrobenzofuran-3-carboxylate

Conditions
ConditionsYield
With dihydrogen peroxide; calcium chloride In methanol at 20℃; for 0.5h; pH=4; aq. buffer; Enzymatic reaction; regiospecific reaction;90%
Methyl ferulate
2309-07-1

Methyl ferulate

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

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

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 20℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox;89%
With Sporotrichum thermophile type C feruloyl esterase; water Enzyme kinetics;
Methyl ferulate
2309-07-1

Methyl ferulate

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

(E)-methyl 3-(4-(ethoxymethoxy)-3-methoxyphenyl)acrylate

(E)-methyl 3-(4-(ethoxymethoxy)-3-methoxyphenyl)acrylate

Conditions
ConditionsYield
Stage #1: Methyl ferulate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: ethyl chloromethyl ether In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;
89%
1-methyl-3-pyrrolidinol
13220-33-2

1-methyl-3-pyrrolidinol

Methyl ferulate
2309-07-1

Methyl ferulate

(E)-methyl 3-(3-methoxy-4-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylate

(E)-methyl 3-(3-methoxy-4-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; triphenylphosphine In tetrahydrofuran at 0℃; for 0.5h;89%
Methyl ferulate
2309-07-1

Methyl ferulate

dimethyl 8,8-dimethoxy-7-oxo-1,4-(1,1-dimethoxy-2-oxoethano)-1,4,4a,7,8,8a-hexahydronaphthalene-2,4a-diyldiacrylate

dimethyl 8,8-dimethoxy-7-oxo-1,4-(1,1-dimethoxy-2-oxoethano)-1,4,4a,7,8,8a-hexahydronaphthalene-2,4a-diyldiacrylate

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In methanol; dichloromethane at 25℃; for 14h; Diels-Alder reaction; Inert atmosphere;87%
methanol
67-56-1

methanol

Methyl ferulate
2309-07-1

Methyl ferulate

C24H28O10

C24H28O10

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In dichloromethane at 25℃; for 14h;87%
Methyl ferulate
2309-07-1

Methyl ferulate

(2E)-3-(3-methoxy-4-hydroxyphenyl)-N-hydroxy-2-propenamide
1431320-14-7

(2E)-3-(3-methoxy-4-hydroxyphenyl)-N-hydroxy-2-propenamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In 1,4-dioxane; water at 20℃; for 24h;87%
Methyl ferulate
2309-07-1

Methyl ferulate

N-(2-chloroacetyl)-3-chloro-4-fluoroaniline
96980-64-2

N-(2-chloroacetyl)-3-chloro-4-fluoroaniline

methyl (2E)-3-(4-{2-[(3-chloro-4-fluorophenyl)amino]-2-oxoethoxy}-3-methoxyphenyl)acrylate

methyl (2E)-3-(4-{2-[(3-chloro-4-fluorophenyl)amino]-2-oxoethoxy}-3-methoxyphenyl)acrylate

Conditions
ConditionsYield
Stage #1: Methyl ferulate With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere;
Stage #2: N-(2-chloroacetyl)-3-chloro-4-fluoroaniline In acetone for 10h; Reflux; Inert atmosphere;
85.65%
(+/-)-2-[1-(2-chloroacetoxy)pentyl]benzoic acid
1107060-38-7

(+/-)-2-[1-(2-chloroacetoxy)pentyl]benzoic acid

Methyl ferulate
2309-07-1

Methyl ferulate

(±)-(E)-2-methoxy-4-(3-methoxy-3-oxoprop-1-en-1-yl)phenyl 2-(1-(2-chloroacetoxy)pentyl)benzoate

(±)-(E)-2-methoxy-4-(3-methoxy-3-oxoprop-1-en-1-yl)phenyl 2-(1-(2-chloroacetoxy)pentyl)benzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;85%
4-bromo-buta-1,2-diene
18668-68-3

4-bromo-buta-1,2-diene

Methyl ferulate
2309-07-1

Methyl ferulate

C15H16O4

C15H16O4

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;84%

2309-07-1Relevant articles and documents

Firmosides A and B: two new sucrose ferulates from the aerial parts of Silene firma and evaluation of radical scavenging activities

Uyen, Nguyen Hoang,Widyowati, Retno,Sulistyowaty, Melanny Ika,Sugimoto, Sachiko,Yamano, Yoshi,Kawakami, Susumu,Otsuka, Hideaki,Matsunami, Katsuyoshi

, p. 796 - 803 (2020)

Abstract: Two new tri-ferulates of sucrose, firmosides A and B (1 and 2, respectively), together with 18 known compounds (3–20), were isolated from the aerial parts of Silene firma. The structures of the isolated compounds were elucidated by various spectroscopic methods, including 1D, 2D NMR, and high-resolution electro-spray ionization–mass spectrometry (HR-ESI–MS). All the isolated compounds were evaluated for their free radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. As a result, two new compounds (1, 2) and 11 demonstrated significant radical scavenging activity, implying the usefulness as antioxidant agents. Graphic Abstract: [Figure not available: see fulltext.].

Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones, and related Michael reaction acceptors: Correlation of potencies as phase 2 enzyme inducers and radical scavengers

Dinkova-Kostova, Albena T.,Abeygunawardana, Chitrananda,Talalay, Paul

, p. 5287 - 5296 (1998)

Induction of phase 2 enzymes (e.g., glutathione transferases, NAD(P)H:quinone reductase, glucuronosyltransferases, epoxide hydrolase) is a major strategy for reducing the susceptibility of animal cells to neoplasia and other forms of electrophile toxicity. In a search for new chemoprotective enzyme inducers, a structure-activity analysis was carried out on two types of naturally occurring and synthetic substituted phenylpropenoids: (a) Ar- CH=CH-CO-R, where R is OH, OCH3, CH3, or Ar, including cinnamic, coumaric, ferulic, and sinapic acid derivatives, their ketone analogues, and chalcones; and (b) bis(benzylidene)cycloalkanones, Ar-CH=C(CH2)(n)(CO)C=CH-Ar, where n = 5, 6, or 7. The potencies of these compounds in inducing NAD(P)H:quinone reductase activity in murine hepatoma cells paralleled their Michael reaction acceptor activity (Talalay, P.; De Long, M. J.; Prochaska, H. J. Proc. Natl. Acad. Sci. U.S.A. 85, 1988, 8261-8265). Unexpectedly, the bis(benzylidene)cycloalkanones also powerfully quenched the lucigenin- derived chemiluminescence evoked by superoxide radicals. Introduction of o- hydroxyl groups on the aromatic rings of these phenylpropenoids dramatically enhanced their potencies not only as inducers for quinone reductase but also as quenchers of superoxide. These potentiating o-hydroxyl groups are hydrogen-bonded, as shown by moderate down field shift of their proton NMR resonances and their sensitivities to the solvent environment. The finding that the potencies of a series of bis(benzylidene)cycloalkanones in inducing quinone reductase appear to be correlated with their ability to quench superoxide radicals suggests that the regulation of phase 2 enzymes may involve both Michael reaction reactivity and radical quenching mechanisms.

Structure of Three Diacylated Anthocyanins Isolated from Red Cabbage, Brassica oleracea

Idaka, Eiichi,Yamakita, Hiroshi,Ogawa, Toshihiko,Kondo, Tadao,Yamamoto, Manabu,Goto, Toshio

, p. 1213 - 1216 (1987)

Three diacylated anthocyanins were isolated from Brassica oleracea and their structures determined to be 3-O-(6-O-acyl-2-O-(2-O-sinapyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidins, in wich the acyl groups were p-coumaryl, ferulyl, and sinapyl, respectively.

Flavonoid glycosides from the leaves of Allium victorialis var. platyphyllum and their anti-neuroinflammatory effects

Woo, Kyeong Wan,Moon, Eunjung,Park, So Young,Kim, Sun Yeou,Lee, Kang Ro

, p. 7465 - 7470 (2012)

Eight new flavonoid glycosides, named allivictoside A-H (1-8), together with twelve known flavonoids (9-20) were isolated from the leaves of Allium victorialis var. platyphyllum. The structures of 1-8 were determined by chemical and spectroscopic methods,

A new approach for synthesis of erythro 8-0-4′ neolignans

Chen, XiaoChuan,Gu, WenXin,Jing, XiaoBi,Pan, XinFu

, p. 557 - 564 (2002)

Erythro- 1-(4-hydroxy-3-methoxyphenyl)-2- (4-formyl-2-methoxy-phenoxy)-propane-1,3-diol, a 8-0-4′ norneolignan, has been stereoselectively synthesized in eight steps from ferulic acid. In this new route to prepare erythro 8-0-4′ neolignans the cis addition of mCPBA to a double bond with high regioselectivity was a key step, and its mechanism is discussed.

Optimization of the reaction conditions for the synthesis of dihydrobenzofuran neolignans

Crotti, Ant?nio E. M.,Dias, Herbert J.,Rodrigues, Matheus L.

, p. 20 - 28 (2020/12/28)

We have optimized the experimental conditions for the silver(I)-promoted oxidative coupling of methyl p-coumarate (I) and methyl ferulate (II), which is the most frequently used methodology to synthesize the bioactive dihydrobenzofuran neolignans 1 ((±)-trans-dehydrodicoumarate dimethyl ester) and 2 ((±)-trans-dehydrodiferulate dimethyl ester). Most of the tested conditions affected the conversion (i.e., the consumption of I and II) and the selectivity (i.e., the percentage of I and II that was converted into 1 and 2, respectively), so the optimized conditions were the ones that afforded the best balance between conversion and selectivity. Silver(I) oxide (0.5 equiv.) is the most efficient oxidant agent amongst the silver(I) reagents that were tested to convert methyl esters I and II into compounds 1 and 2, respectively. Acetonitrile, which has not yet been reported as a solvent for this reaction, provided the best balance between conversion and selectivity, besides being "greener" than other solvents that are more often employed (e.g., dichloromethane and benzene). Under the optimized conditions, the reaction time decreased from 20 to 4 h without significantly impacting the conversion and selectivity.

Synthesis of Novel Antiviral Ferulic Acid-Eugenol and Isoeugenol Hybrids Using Various Link Reactions

Gan, Xiuhai,Wang, Zhengxing,Hu, Deyu

, p. 13724 - 13733 (2021/11/23)

To develop novel antiviral agents, some novel conjugates between ferulic acid and eugenol or isoeugenol were designed and synthesized by the link reaction. The antiviral activities of compounds were evaluated using the half leaf dead spot method. Bioassay results showed acceptable antiviral activities of some conjugates against the tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). Compounds A9, A10, E1, and E4 showed remarkable curative, protective, and inactivating effects on TMV and CMV at 500 μg mL-1. Notably, these compounds exhibited excellent protective effects on TMV and CMV. The EC50 values of compounds A9, A10, E1, and E4 against TMV were 180.5, 169.5, 211.4, and 135.5 μg mL-1, respectively, and those against CMV were 210.5, 239.1, 218.4, and 178.6 μg mL-1, respectively, which were superior to those of ferulic acid (471.5 and 489.2 μg mL-1), eugenol (456.3 and 463.2 μg mL-1), isoeugenol (478.4 and 487.5 μg mL-1), and ningnanmycin (246.5 and 286.6 μg mL-1). Then, the antiviral mechanisms of compound E4 were investigated by determining defensive enzyme activities and multi-omics analysis. The results indicated that compound E4 resisted the virus infection by enhancing defensive responses via inducing the accumulation of secondary metabolites from the phenylpropanoid biosynthesis pathway in tobacco.

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