Ethyl 4'-hydroxy-3'-methoxycinnamate supplier

Name
Ethyl 4'-hydroxy-3'-methoxycinnamate
EINECS 223-745-5
CAS No. 4046-02-0
Article Data90
CAS DataBase
Density 1.173 g/cm³
Solubility
Melting Point 63-65 °C(lit.)
Formula C₁₂H₁₄O₄
Boiling Point 382.3 °C at 760 mmHg
Molecular Weight 222.241
Flash Point 132.5 °C
Transport Information
Appearance
Safety 26-37/39-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Ethyl ferulate;2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, ethyl ester;UNII-5B8915UELW;AI3-23714;
PSA 55.76000
LogP 1.97710

Synthetic route

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

: 64-17-5
ethanol

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
With acetyl chloride at 20℃;	100%
With sulfuric acid at 88℃; under 1034.32 Torr; for 0.05h; Microwave irradiation;	94%
With sulfuric acid for 4h; Reflux;	94%

: 1071-46-1
hydrogen ethyl malonate

: 121-33-5
vanillin

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
Stage #1: hydrogen ethyl malonate; vanillin With piperidine; pyridine at 100℃; for 24h; Knoevenagel Condensation; Stage #2: With hydrogenchloride In water at -10 - 0℃; for 24h;	98%
With piperidine In pyridine at 100℃; for 8h; Knoevenagel Condensation;	97%
With piperidine; pyridine; aniline
With pyridine Knoevenagel Condensation; Reflux;

: 6635-27-4
ethyl (E)-3-(4-acetoxy-3-methoxyphenyl)-prop-2-enoate

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
With ammonium acetate In methanol at 20℃; for 3.5h;	98%
With silica-supported phosphomolybdic acid In methanol at 20℃; for 2h;	96%

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

: 64-17-5
ethanol

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
With sulfuric acid for 12h;	96%
With sulfuric acid Reflux;	92%
With acetyl chloride at 0 - 20℃; Inert atmosphere;	86%
With sulfuric acid Fischer-Speier Esterification; Sealed tube; Heating; Microwave irradiation;

: 121-33-5
vanillin

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
In toluene for 4h; Wittig Olefination; Reflux;	95%
In chloroform Reflux;	85%
In chloroform for 5h; Wittig Olefination; Inert atmosphere; Reflux;	85%

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

: 140-88-5
ethyl acrylate

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
With Hoveyda-Grubbs catalyst first generation In 1,2-dichloro-ethane at 70℃; Cross Metathesis; Schlenk technique; Inert atmosphere; Glovebox;	95%

: ethyl (E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)acrylate

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
bismuth(lll) trifluoromethanesulfonate In tetrahydrofuran; water at 20℃; for 0.166667h;	92%

: 64-17-5
ethanol

: 138769-50-3, 108608-04-4
trans-4-hydroxy-3-methoxycinnamic acid chloride

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
With pyridine; potassium carbonate In dichloromethane; chloroform; toluene at 70℃; for 6h; Temperature; Reagent/catalyst;	87.8%
With pyridine; potassium carbonate; triethylamine In dichloromethane; chloroform; toluene at 70℃; for 6h; Solvent; Reagent/catalyst; Concentration; Temperature; Time;	87.8%

: 1530-45-6
(carbethoxymethyl)triphenylphosphonium bromide

: 121-33-5
vanillin

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
With Amberlite IR-400 In N,N-dimethyl-formamide at 95℃; for 10h; Inert atmosphere;	80%

: 121-33-5
vanillin

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

A: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 4046-02-0, 28028-62-8, 74257-26-4
cis-3-(4-Hydroxy-3-methoxyphenyl)-2-propensaeure-ethylester

Conditions

Conditions	Yield
In dichloromethane at 50℃; under 10000 Torr; for 12h; Product distribution; other solvent, time, pressure, other sibstituent. aldehydes;
In dichloromethane at 50℃; under 10000 Torr; for 12h; Yield given. Yields of byproduct given;
In dichloromethane at 50℃; for 12h; normal pressure; Yield given. Yields of byproduct given;

...Expand

: 121-33-5
vanillin

iron (II)-chloride: iron (II)-chloride

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: H2SO4 View Scheme

: 121-33-5
vanillin

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

A: 74257-26-4
ethyl (2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

B: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
In benzene Wittig Olefination; Reflux; Overall yield = 81 %;	A n/a B n/a
In benzene for 1h; Wittig Olefination; Inert atmosphere; Reflux; Overall yield = 96 %; Overall yield = 5.6 g;
In dichloromethane for 18h; Wittig Olefination; Inert atmosphere; Overall yield = 94 %; Overall yield = 4.13 g;	A n/a B n/a
In benzene at 80℃; for 4.5h; Wittig Olefination; Inert atmosphere; Overall yield = 99 %; Overall yield = 11.638 g;	A n/a B n/a

...Expand

: 1530-45-6
(carbethoxymethyl)triphenylphosphonium bromide

: 121-33-5
vanillin

A: 74257-26-4
ethyl (2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

B: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
Stage #1: (carbethoxymethyl)triphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: vanillin In tetrahydrofuran at -78 - 20℃; for 50h; Overall yield = 85 %; Overall yield = 1.25 g;	A n/a B n/a

...Expand

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

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride; N,N-dimethyl-formamide / dichloromethane; toluene / 6 h / 70 °C 2: potassium carbonate; pyridine / dichloromethane; toluene; chloroform / 6 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane; toluene / 6 h / 70 °C 2: potassium carbonate; triethylamine; pyridine / dichloromethane; toluene; chloroform / 6 h / 70 °C View Scheme
With boron trifluoride methanol complex for 0.05h; Reflux;

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

: 75-36-5
acetyl chloride

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
In ethanol at 20℃;

: (E)-ethyl 3-(4-(((4,5-dimethoxy-2-nitrobenzyl)sulfonyl)oxy)-3-methoxyphenyl)acrylate

A: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

B: 119137-07-4
4,5-dimethoxy-2-nitrosobenzaldehyde

Conditions

Conditions	Yield
In aq. phosphate buffer; acetonitrile pH=7.4; UV-irradiation;

: (Z)-2-(2,4-dihydroxyphenyl)-4-(4-((E)-3-ethoxy-3-oxoprop-1-en-1-yl)-2-methoxyphenoxy)-4-oxobut-2-en-1-yl 2-hydroxybenzoate

A: 151889-83-7
7-hydroxy-4-(hydroxylmethyl)-2H-chromen-2-one

B: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
In water; acetonitrile for 1h; UV-irradiation;

: 121-33-5
vanillin

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: piperidine; p-toluidine / toluene / 3 h / 80 °C 2: sulfuric acid / 75 °C View Scheme

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 61292-90-8
ethyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 2h;	100%
Hydrogenation;
With samarium diiodide; tert-butyl alcohol In hexane at 30℃; Kinetics;

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

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

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water for 3h; Reflux;	100%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 8h;	98%
With Sporotrichum thermophile type C feruloyl esterase; water Enzyme kinetics;
With recombinant Tan410 In aq. phosphate buffer at 35℃; for 0.75h; pH=7; Enzymatic reaction;

: 95-65-8
3,4-Dimethylphenol

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 4-(4-hydroxy-3-methoxyphenyl)-6,7-dimethyl-3,4-dihydrocoumarin

Conditions

Conditions	Yield
With trifluoroacetic acid at 20℃; for 24h;	100%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 135-19-3
β-naphthol

: 1,2-dihydro-1-(4-hydroxy-3-methoxyphenyl)-3H-naphtho[2,1-b]pyran-3-one

Conditions

Conditions	Yield
With trifluoroacetic acid at 20℃; for 24h;	100%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 58479-61-1
tert-butylchlorodiphenylsilane

: (E)-ethyl 3-(4-((tert-butyldiphenylsilyl)oxy)-3-methoxyphenyl)acrylate

Conditions

Conditions	Yield
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	100%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 107-30-2
chloromethyl methyl ether

: ethyl (E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)acrylate

Conditions

Conditions	Yield
Stage #1: ethyl 4-hydroxy-3-methoxycinnamate With potassium carbonate In acetone at 20℃; for 1h; Stage #2: chloromethyl methyl ether In acetone at 0 - 20℃; for 6h;	98%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 1-(2'-methoxybenzyl)-4-chloroethyl piperidine

: C27H35NO5

Conditions

Conditions	Yield
With pyridine; potassium carbonate In dichloromethane; chloroform; toluene at 70℃; for 6h; Temperature; Reagent/catalyst;	97.8%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 108-68-9
3,5-Dimethylphenol

: 4-(4-hydroxy-3-methoxyphenyl)-5,7-dimethyl-3,4-dihydrocoumarin

Conditions

Conditions	Yield
With trifluoroacetic acid at 20℃; for 24h;	97%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 106-93-4
ethylene dibromide

: ethyl (E)-3-(4-(2-bromoethoxy)-3-methoxyphenyl)acrylate

Conditions

Conditions	Yield
With pyridine; potassium carbonate In dichloromethane; chloroform; toluene at 70℃; for 6h; Solvent; Reagent/catalyst; Concentration; Temperature; Time;	95.3%
With potassium carbonate In acetone at 65℃;	68%
Stage #1: ethyl 4-hydroxy-3-methoxycinnamate With potassium carbonate In butanone at 20℃; for 1h; Stage #2: ethylene dibromide In butanone at 80℃;

: 112-60-7
Tetraethylene glycol

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: (E)-3-(4-{2-[2-(2-{2-[4-((E)-2-Ethoxycarbonyl-vinyl)-2-methoxy-phenoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-3-methoxy-phenyl)-acrylic acid ethyl ester

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.0833333h; Mitsunobu reaction;	95%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 134179-43-4
11-azide-1-{(methylsulfonyl)oxy}-3,6,9-trioxaundecane

: 1437306-80-3
(E)-3-(4-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethoxy)-3-methoxyphenyl)acrylic acid ethyl ester

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃;	94%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1485529-16-5
(E)-ethyl 3-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)acrylate

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 2h;	90%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	90%

: 629-03-8
1 ,6-dibromohexane

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: (E)-ethyl 3-(4-((6-bromohexyl)oxy)-3-methoxyphenyl)acrylate

Conditions

Conditions	Yield
With potassium carbonate; sodium iodide In acetone for 8h; Reflux;	90%
With potassium carbonate In acetone at 65℃;	65%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 75-36-5
acetyl chloride

: 6635-27-4
ethyl (E)-3-(4-acetoxy-3-methoxyphenyl)-prop-2-enoate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1h; Cooling with ice;	90%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: 74-88-4
methyl iodide

: 20583-78-2, 24393-65-5
ethyl (E)-3,4-dimethoxycinnamate

Conditions

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	89%
With potassium carbonate In acetone

: 6138-90-5
trans-geranyl bromide

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: ethyl 3-(4'-geranyloxy-3'-methoxyphenyl)-2-propenoate

Conditions

Conditions	Yield
With potassium carbonate In acetone for 2h; Heating;	89%

: 1754-49-0
diethyl phenylphosphonate

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: (E)-ethyl 3-(4-((ethoxy(phenyl)phosphoryl)oxy)-3-methoxyphenyl)acrylate

Conditions

Conditions	Yield
Stage #1: diethyl phenylphosphonate With pyridine; trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 0.166667h; Sealed tube; Stage #2: ethyl 4-hydroxy-3-methoxycinnamate In dichloromethane at 20℃; for 0.5h; Sealed tube;	87%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

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

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; benzyl chloride In tetrahydrofuran at 0 - 20℃;	85%
With lithium aluminium tetrahydride; benzyl chloride In tetrahydrofuran at 20℃;	83%
With diisobutylaluminium hydride In toluene at -78 - 20℃; for 4.5h; Inert atmosphere;	83%

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

A: 5-((E)-2-Ethoxycarbonyl-vinyl)-7-methoxy-benzofuran-3-carboxylic acid ethyl ester

B: (2E,3E)-diethyl 2,3-bis(4-hydroxy-3-methoxybenzylidene)succinate

Conditions

Conditions	Yield
With potassium hydroxide; potassium hexacyanoferrate(III) In benzene for 0.5h;	A 84% B 9%

: 78-40-0
triethyl phosphate

: 4046-02-0
ethyl 4-hydroxy-3-methoxycinnamate

: (E)-ethyl 3-(4-((diethoxyphosphoryl)oxy)-3-methoxyphenyl)acrylate

Conditions

Conditions	Yield
Stage #1: triethyl phosphate With pyridine; trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 0.166667h; Stage #2: ethyl 4-hydroxy-3-methoxycinnamate In dichloromethane at 20℃; for 0.5h;	84%

Ethyl 4'-hydroxy-3'-methoxycinnamate Chemical Properties

Molecular structure of Ethyl ferulate (CAS NO.4046-02-0) is:

Product Name: Ethyl ferulate
CAS Registry Number: 4046-02-0
IUPAC Name: ethyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Molecular Weight: 222.23716 [g/mol]
Molecular Formula: C₁₂H₁₄O₄
XLogP3: 2.2
H-Bond Donor: 1
H-Bond Acceptor: 4
EINECS: 223-745-5
Melting Point: 63-65 °C(lit.)
Surface Tension: 43.4 dyne/cm
Sensitive: Light Sensitive
Density: 1.173 g/cm³
Flash Point: 132.5 °C
Enthalpy of Vaporization: 65.54 kJ/mol
Boiling Point: 382.3 °C at 760 mmHg
Vapour Pressure: 2.17E-06 mmHg at 25°C
Product Categories: Aromatic Esters; Cinnamic acid

Ethyl 4'-hydroxy-3'-methoxycinnamate Safety Profile

Safty information about Ethyl ferulate (CAS NO.4046-02-0) is:
Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
S36:Wear suitable protective clothing.
WGK Germany: 3
Hazard Note: Irritant

Ethyl 4'-hydroxy-3'-methoxycinnamate Specification

Ethyl ferulate , its cas register number is 4046-02-0. It also can be called AI3-23714 ; UNII-5B8915UELW ; 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, ethyl ester ; Ethyl 4'-hydroxy-3'-methoxycinnamate .

Product Name

Ethyl 4'-hydroxy-3'-methoxycinnamate

Synthetic route

Ethyl 4'-hydroxy-3'-methoxycinnamate Chemical Properties

Ethyl 4'-hydroxy-3'-methoxycinnamate Safety Profile

Ethyl 4'-hydroxy-3'-methoxycinnamate Specification

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