Methyl 4-hydroxy-3-methoxycinnamate supplier

Name
FERULIC ACID METHYL ESTER
EINECS 1308068-626-2
CAS No. 2309-07-1
Article Data156
CAS DataBase
Density 1.205 g/cm³
Solubility Slightly soluble in water.
Melting Point 62-65 °C
Formula C₁₁H₁₂O₄
Boiling Point 338.077 °C at 760 mmHg
Molecular Weight 208.214
Flash Point 130.409 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms Cinnamic acid,4-hydroxy-3-methoxy-, methyl ester (6CI,7CI,8CI);Ferulic acid methyl ester;Methyl 4'-hydroxy-3'-methoxycinnamate;Methyl ferulate;NSC 74548;
PSA 55.76000
LogP 1.58700

Synthetic route

: 67-56-1
methanol

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

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
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%

: 220300-07-2
methyl (E)-4-methoxymethyl-3-methoxycinnamate

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 0.5h; Heating;	100%

: 121-33-5
vanillin

: 21204-67-1
methyl (triphenylphosphoranylidene)acetate

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
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%

: 67-56-1
methanol

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

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
	98%

: 67-56-1
methanol

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

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
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

: 292638-85-8
acrylic acid methyl ester

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With palladium diacetate In methanol at 20℃; Heck Reaction;	96%

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

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;	94%

: 259267-38-4
methyl (E)-3-(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)acrylate

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 2h;	90%

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

: 292638-85-8
acrylic acid methyl ester

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With Hoveyda-Grubbs catalyst first generation In 1,2-dichloro-ethane at 70℃; Cross Metathesis; Schlenk technique; Inert atmosphere; Glovebox;	90%

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

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
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

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

: 77-78-1
dimethyl sulfate

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With potassium hydrogencarbonate In acetone at 20℃; for 1.5h;	84%

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

: 2309-07-1
Methyl ferulate

Conditions

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

: 67-56-1
methanol

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

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

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

C: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With hydrogenchloride at 65℃; for 4h;	A n/a B n/a C 70%

...Expand

: 186581-53-3, 908094-01-9
diazomethane

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

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
In diethyl ether at 0℃; for 2h;	69%
With methanol
In diethyl ether Esterification;
In methanol at 20℃; for 4h; Methylation;

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

: 67-48-1
choline chloride

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With urea at 140℃; for 2h; Green chemistry;	55%

: 67-56-1
methanol

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

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With pyridine

: 67-56-1
methanol

: 120601-64-1
regaloside G

A: 2309-07-1
Methyl ferulate

B: 534-68-9, 3879-81-0, 5768-72-9, 6245-27-8, 10588-30-4, 22160-26-5, 40593-14-4, 128163-38-2, 5624-47-5
2-O-β-D-glucosyl-glycerol

Conditions

Conditions	Yield
With sodium methylate for 1h; Ambient temperature;

...Expand

: 67-56-1
methanol

: 94492-21-4
cistanoside D

A: 2380-78-1
homovanillyl alcohol

B: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With acetyl chloride for 0.5h; Heating;

...Expand

: 67-56-1
methanol

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

B: 2309-07-1
Methyl ferulate

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

Conditions

Conditions	Yield
With sodium methylate

...Expand

: 124-41-4
sodium methylate

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

A: 2309-07-1
Methyl ferulate

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

Conditions

Conditions	Yield
In methanol for 8h; Ambient temperature;

...Expand

: 124-41-4
sodium methylate

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

A: 3943-97-3
methyl 4-hydroxycinnamate

B: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
In methanol for 0.166667h; Product distribution; Heating;

...Expand

: 120601-64-1
regaloside G

A: 2309-07-1
Methyl ferulate

B: 534-68-9, 3879-81-0, 5768-72-9, 6245-27-8, 10588-30-4, 22160-26-5, 40593-14-4, 128163-38-2, 5624-47-5
2-O-β-D-glucosyl-glycerol

Conditions

Conditions	Yield
With sodium methylate In methanol for 1h; Ambient temperature;

: 83404-71-1
6'-trans feruloyl lyaloside

A: 2309-07-1
Methyl ferulate

B: 56021-85-3
lyaloside

Conditions

Conditions	Yield
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

A: 42041-51-0
methyl (E)-sinapate

B: 2309-07-1
Methyl ferulate

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

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 0℃;

...Expand

: 84638-29-9
Rhynchophine

A: 2309-07-1
Methyl ferulate

B: 23141-27-7, 22621-94-9, 23141-25-5
3β(R)-vincosamide

Conditions

Conditions	Yield
With sodium methylate In methanol	A 4 mg B 3 mg

: 94393-06-3
4-O-β-D-glucopyranosyl-(E)-ferulic acid methyl ester

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With sulfuric acid In ethanol for 2h;

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

B: 2309-07-1
Methyl ferulate

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

Conditions

Conditions	Yield
With sodium methylate In methanol

...Expand

: acuminatuside

A: 2309-07-1
Methyl ferulate

B: 479-98-1
aucubin

Conditions

Conditions	Yield
With sodium methylate In methanol at 22℃; for 1h;

: 67-56-1
methanol

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

A: 2309-07-1
Methyl ferulate

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

: 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

Conditions

Conditions	Yield
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

...Expand

: 2309-07-1
Methyl ferulate

: 108-24-7
acetic anhydride

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

Conditions

Conditions	Yield
With pyridine	100%
With pyridine In ethyl acetate at 20℃;	91%
With triethylamine In dichloromethane at 20℃; for 4h;	85%

: 2309-07-1
Methyl ferulate

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

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In methanol	100%
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%

: 2309-07-1
Methyl ferulate

: 18162-48-6
tert-butyldimethylsilyl chloride

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

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 2h;	99%

: 2309-07-1
Methyl ferulate

: 458-35-5, 32811-40-8, 69056-21-9
coniferal alcohol

Conditions

Conditions	Yield
With diisobutylaluminium hydride In toluene	98%
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%

: 2309-07-1
Methyl ferulate

: 100-39-0
benzyl bromide

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

Conditions

Conditions	Yield
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%

: 2309-07-1
Methyl ferulate

: 100-44-7
benzyl chloride

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

Conditions

Conditions	Yield
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;

: 2309-07-1
Methyl ferulate

: 96-32-2
bromoacetic acid methyl ester

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

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Alkylation;	94%

: 358-23-6
trifluoromethylsulfonic anhydride

: 2309-07-1
Methyl ferulate

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

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 24h; Inert atmosphere;	91%

: 2309-07-1
Methyl ferulate

: 106-96-7
propargyl bromide

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

Conditions

Conditions	Yield
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%

: 2309-07-1
Methyl ferulate

: 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

Conditions	Yield
With dihydrogen peroxide; calcium chloride In methanol at 20℃; for 0.5h; pH=4; aq. buffer; Enzymatic reaction; regiospecific reaction;	90%

: 2309-07-1
Methyl ferulate

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

Conditions

Conditions	Yield
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;

: 2309-07-1
Methyl ferulate

: 3188-13-4
ethyl chloromethyl ether

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

Conditions

Conditions	Yield
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%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 2309-07-1
Methyl ferulate

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

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; triphenylphosphine In tetrahydrofuran at 0℃; for 0.5h;	89%

: 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

Conditions

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

: 67-56-1
methanol

: 2309-07-1
Methyl ferulate

: C24H28O10

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene In dichloromethane at 25℃; for 14h;	87%

: 2309-07-1
Methyl ferulate

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

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In 1,4-dioxane; water at 20℃; for 24h;	87%

: 2309-07-1
Methyl ferulate

: 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

Conditions

Conditions	Yield
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%

: 1107060-38-7
(+/-)-2-[1-(2-chloroacetoxy)pentyl]benzoic acid

: 2309-07-1
Methyl ferulate

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

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	85%

: 18668-68-3
4-bromo-buta-1,2-diene

: 2309-07-1
Methyl ferulate

: C15H16O4

Conditions

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

Methyl 4-hydroxy-3-methoxycinnamate Specification

The CAS register number of Methyl 4-hydroxy-3-methoxycinnamate is 2309-07-1. It also can be called as Methyl 3-(4-hydroxy-3-methoxyphenyl)acrylate and the IUPAC name about this chemical is methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate. The molecular formula about this chemical is C₁₁H₁₂O₄ and the molecular weight is 208.21. It belongs to the Aromatic Esters.

Physical properties about Methyl 4-hydroxy-3-methoxycinnamate are: (1)ACD/LogP: 1.41; (2)ACD/LogD (pH 5.5): 1.4; (3)ACD/LogD (pH 7.4): 1.39; (4)ACD/BCF (pH 5.5): 6.88; (5)ACD/BCF (pH 7.4): 6.66; (6)ACD/KOC (pH 5.5): 138.41; (7)ACD/KOC (pH 7.4): 134.04; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 44.76Å²; (12)Index of Refraction: 1.574; (13)Molar Refractivity: 57.11 cm³; (14)Molar Volume: 172.8 cm³; (15)Polarizability: 22.64x10^-24cm³; (16)Surface Tension: 44.5 dyne/cm; (17)Enthalpy of Vaporization: 60.44 kJ/mol; (18)Boiling Point: 338.1 °C at 760 mmHg; (19)Vapour Pressure: 5.13E-05 mmHg at 25°C.

Uses of Methyl 4-hydroxy-3-methoxycinnamate: it can be used to produce 3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid 2,3,4,5,6-pentahydroxy-hexyl ester with D-mannitol. This reaction will need reagent K₂CO₃ and solvent dimethylformamide. The yield is about 30.4%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)\C=C\c1cc(OC)c(O)cc1
(2)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+
(3)InChIKey: AUJXJFHANFIVKH-GQCTYLIABZ
(4)Std. InChI: InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3/b6-4+
(5)Std. InChIKey: AUJXJFHANFIVKH-GQCTYLIASA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	1189mg/kg (1189mg/kg)		Indian Journal of Experimental Biology. Vol. 25, Pg. 187, 1987.

Product Name

FERULIC ACID METHYL ESTER

Synthetic route

Methyl 4-hydroxy-3-methoxycinnamate Specification

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