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1135-24-6

Basic Information
CAS No.: 1135-24-6
Name: 4-Hydroxy-3-methoxycinnamic acid
Molecular Structure:
Molecular Structure of 1135-24-6 (4-Hydroxy-3-methoxycinnamic acid)
Formula: C10H10O4
Molecular Weight: 194.19
Synonyms: 2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-;(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate;3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acid;3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid;caffeic acid 3-methyl ether;3-(4-Hydroxy-3-methoxyphenyl)acrylic acid;2-Propenoic acid,3-(4-hydroxy-3-methoxyphenyl)-;2-Propenoic acid, 3- (4-hydroxy-3-methoxyphenyl)-;Ferulate;3-Methoxy-4-hydroxy-trans-cinnamate;Cinnamic acid, 4-hydroxy-3-methoxy-;3-methoxy-4-hydroxycinnamic acid;Natural ferulic acid;Ferulic acid 99.5%;FerulicAcid;Gamma-Oryzanol, Ferulic acid;Fumalic acid;
EINECS: 214-490-0
Density: 1.316 g/cm3
Melting Point: 168-172 °C(lit.)
Boiling Point: 372.3 °C at 760 mmHg
Flash Point: 150.5 °C
Solubility: Soluble in water
Appearance: Pale Yellow Solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
Transport Information:
PSA: 66.76000
LogP: 1.49860
Synthetic route
4046-02-0

ethyl 4-hydroxy-3-methoxycinnamate

1135-24-6

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

Conditions
ConditionsYield
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;
141-82-2

malonic acid

121-33-5

vanillin

1135-24-6

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

Conditions
ConditionsYield
With piperidine; pyridine for 0.0833333h; microwave irradiation;94%
With piperidine; p-toluidine In toluene at 80℃; for 3h; Knoevenagel Condensation;94%
With bismuth(III) chloride for 0.0833333h; Doebner condensation; Microwave irradiation; Neat (no solvent);93%

(E)-methoxymethyl 3-[3-methoxy-4-(methoxymethoxy)phenyl]acrylate

1135-24-6

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

Conditions
ConditionsYield
bismuth(lll) trifluoromethanesulfonate In tetrahydrofuran; water at 20℃; for 0.416667h;90%
2309-07-1

Methyl ferulate

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;
141-82-2

malonic acid

148-53-8

3-methoxy-2-hydroxybenzaldehyde

1135-24-6

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

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 60℃; for 8h; Knoevenagel-Doebner condensation;83%

A

1135-24-6

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

B

121-33-5

vanillin

C

(1E,4Z,8Z,11E)-5,8-Dihydroxy-1,12-bis-(4-hydroxy-3-methoxy-phenyl)-6,7-bis-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-dodeca-1,4,8,11-tetraene-3,10-dione

Conditions
ConditionsYield
With 5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinatoiron(III) chloride; dihydrogen peroxide; acetylacetone In dichloromethane at 20℃; for 2.5h;A 2.1%
B 3.3%
C 70%

C10H9IO3

1135-24-6

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

Conditions
ConditionsYield
With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide In water at 120℃; for 6h;60%
85364-70-1

3-methyl-4-nitro-5-<2-(3-methoxy-4-hydroxyphenyl)ethenyl>isoxazole

1135-24-6

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

Conditions
ConditionsYield
With sodium hydroxide for 2h; Heating;49.7%
331-39-5

caffeic acid

S-(5’-adenosyl)-L-methionine chloride

1135-24-6

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

Conditions
ConditionsYield
O-methyltransferase pH 7;
63644-62-2, 123821-69-2, 62706-35-8

(E,E)-3-(4-hydroxy-3-methoxyphenyl)allyl 3-(4-hydroxy-3-methoxyphenyl)acrylate

A

1135-24-6

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

C

63644-71-3

(E)-4-(3-methoxy-1-propenyl)-2-methoxyphenol

Conditions
ConditionsYield
Product distribution; hydrolysis by various reaction conditions to various product;
2596-47-6, 147677-05-2, 34749-55-8

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

1135-24-6

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

Conditions
ConditionsYield
With potassium hydroxide for 4h; Heating;
131623-14-8

6'-O-trans-feruloylnodakenin

A

2280-44-6

D-Glucose

B

1135-24-6

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

C

495-32-9

(+)-marmesin

Conditions
ConditionsYield
In sulfuric acid for 0.666667h; Heating;
With sulfuric acid for 0.666667h; Heating;
101330-61-4

di-(E)-feruloylspermidine

1135-24-6

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

Conditions
ConditionsYield
With sodium hydroxide at 100℃; for 4h;
96014-22-1

(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

A

61-54-1

tryptamine

B

1135-24-6

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

Conditions
ConditionsYield
In sodium hydroxide
83608-86-0, 78510-19-7

N-trans-feruloyl-3-O-methyldopamine

A

1135-24-6

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

B

554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
With sodium hydroxide
117405-51-3

4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside

A

1135-24-6

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

B

50-99-7

D-glucose

Conditions
ConditionsYield
With sulfuric acid In ethanol for 3h; Heating;A 21 mg
B n/a

A

1135-24-6

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

B

7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sodium hydroxide In water for 2h; Product distribution; Heating;

2-O-<5-O-(trans-feruloyl)-β-L-arabinofuranosyl>-D-xylopyranose

A

58-86-6

D-xylose

B

1135-24-6

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

C

5328-37-0

L-arabinose

Conditions
ConditionsYield
With sodium hydroxide; Aspergillus niger "cellulase" Product distribution;
85011-57-0

scopoletin 7-O-(6-O-feruloyl-β-D-glucopyranoside)

A

2280-44-6

D-Glucose

B

92-61-5

7-hydroxy-6-methoxy-2H-1-benzopyran-2-one

C

1135-24-6

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

Conditions
ConditionsYield
With hydrogenchloride for 6h; Heating; water bath;
85011-57-0

scopoletin 7-O-(6-O-feruloyl-β-D-glucopyranoside)

A

1135-24-6

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

B

531-44-2

scopolin

Conditions
ConditionsYield
With potassium hydroxide In water at 60℃; for 0.583333h;
84873-15-4

(2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 2-(4-hydroxyphenyl)ethyl ester

A

1135-24-6

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

B

60-12-8

2-phenylethanol

Conditions
ConditionsYield
With sodium hydroxide; ethanol for 0.166667h;A 488 mg
B 530 mg
84976-26-1

O-<5-O-(trans-feruloyl)-α-L-arabinofuranosyl>-(1<*>3)-O-β-D-xylopyranosyl-(1<*>4)-D-xylopyranose

A

1135-24-6

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

B

141923-44-6

α-L-arabinofuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-D-xylopyranose

Conditions
ConditionsYield
With sodium hydroxide for 24h; Ambient temperature;
80159-08-6

(E)-6-O-feruloylscandoside methyl ester

A

18842-99-4

deacetylasperulosidic acid

B

1135-24-6

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

Conditions
ConditionsYield
With barium dihydroxide Ambient temperature; Yields of byproduct given;

periclymenoside

A

2280-44-6

D-Glucose

B

1135-24-6

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

Conditions
ConditionsYield
With hydrogenchloride for 3h; Heating;

(E)-caffeoyl-(E)-feruloylspermidine

A

1135-24-6

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

B

331-39-5

caffeic acid

Conditions
ConditionsYield
With sodium hydroxide at 100℃; for 4h; Title compound not separated from byproducts;

cleistophostaudin

A

1135-24-6

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

B

22336-76-1

3-camphanol

Conditions
ConditionsYield
With potassium hydroxide In methanol for 24h; Heating;A 30 mg
B 10 mg

2-hydroxy-3-O-trans-feruloyl-1,2-propanedicarboxylic acid dimethyl ester

1135-24-6

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

Conditions
ConditionsYield
With sodium hydroxide at 90℃; for 0.5h;

8-O-feruloyltovarol

A

1135-24-6

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

B

98941-66-3

angrendiol

Conditions
ConditionsYield
With sodium hydroxide In methanol for 8h; Ambient temperature;A 206 mg
B 223 mg
823788-11-0

(E)-methyl 3-(3-methoxy-4-((methylsulfonyl)oxy)phenyl)acrylate

1135-24-6

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

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 1h; Heating;
67-56-1

methanol

1135-24-6

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

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%
1135-24-6

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

64-17-5

ethanol

4046-02-0

ethyl 4-hydroxy-3-methoxycinnamate

Conditions
ConditionsYield
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%
1135-24-6

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

7786-61-0

3-methoxy-4-hydroxystyrene

Conditions
ConditionsYield
With phosphate buffer; Catharanthus roseus at 25℃; for 72h; pH=6.0;100%
With 4-methoxy-phenol In water; N,N-dimethyl-formamide at 150℃; for 4h;94%
With sodium hydroxide In water at 30℃; for 3h; pH=8.5; Microbiological reaction;93.1%
1135-24-6

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

1135-23-5

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

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate under 760 Torr;100%
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 2068.59 Torr;100%
With hydrogen; palladium on activated charcoal In methanol; ethyl acetate under 2068.59 Torr; for 5h;100%
1135-24-6

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

108-24-7

acetic anhydride

2596-47-6, 147677-05-2, 34749-55-8

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

Conditions
ConditionsYield
With pyridine at 37℃; Inert atmosphere;100%
With chloro-trimethyl-silane; sodium iodide at 20℃; for 0.333333h; Reagent/catalyst;96%
With sodium hydroxide In water at 20℃; for 1.5h; Cooling with ice;95.35%
1135-24-6

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

77-78-1

dimethyl sulfate

5396-64-5

methyl (E)-3-(3,4-dimethoxyphenyl)acrylate

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;100%
With potassium carbonate In acetone for 3h; Reflux;90%
With potassium carbonate In acetone for 36h;4.2 g
With potassium carbonate In acetone
1135-24-6

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

100-39-0

benzyl bromide

94475-61-3

(E)-3-(3-methoxy-4-benzyloxyphenyl)acrylic acid benzyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 48h; Esterification;100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;96%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h;91%
1135-24-6

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

55947-32-5

(E)-3-(3-Methoxy-4-trimethylsilanyloxy-phenyl)-acrylic acid

Conditions
ConditionsYield
100%
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

1135-24-6

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

68573-23-9

(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide99%
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 3-(2-aminoethyl)-1H-indol-5-ol With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;
57%
Stage #1: 3-(2-aminoethyl)-1H-indol-5-ol; (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With pyridine; dicyclohexyl-carbodiimide at 20℃; for 24h;
Stage #2: With potassium hydroxide In methanol at 20℃; for 4h;
1135-24-6

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

ferulic acid sodium salt

Conditions
ConditionsYield
With sodium In ethanol Reflux; Inert atmosphere;99%
With sodium hydroxide In methanol82%
With sodium hydroxide In water Heating;
1135-24-6

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

3970-21-6

2-Methoxyethoxymethyl chloride

(E)-(2-methoxyethoxy)methyl 3-(3-methoxy-4-((2-methoxyethoxy)methoxy)phenyl)acrylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine at 0 - 20℃; Inert atmosphere;99%
1135-24-6

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

Conditions
ConditionsYield
With ATP; NADPH; magnesium chloride In aq. phosphate buffer at 30℃; for 18h; pH=7.5; Green chemistry; Enzymatic reaction;98%
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With chloroformic acid ethyl ester; triethylamine In 1,4-dioxane for 1h; Inert atmosphere;
Stage #2: With sodium tetrahydroborate In 1,4-dioxane; N,N-dimethyl-formamide for 1h; Inert atmosphere;
33%
Multi-step reaction with 2 steps
1: 96 percent / HCl / 48 h / 20 °C
2: 87 percent / LiAlH4 / diethyl ether / 12 h / 20 °C
View Scheme
1135-24-6

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

121-33-5

vanillin

Conditions
ConditionsYield
With tricopper(II) bis(benzene-1,3,5-tricarboxylate) trihydrate; dihydrogen peroxide In ethanol; water; acetonitrile at 100℃; for 1h;98%
With dihydrogen peroxide In ethanol; water; acetonitrile for 4h; Mechanism; Kinetics; Reflux;71%
titanium(IV) oxide In water at 65℃; under 3.75038 Torr; Irradiation;
1135-24-6

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

106-96-7

propargyl bromide

(E)-3-(3-methoxy-4-prop-2-ynoxyphenyl)prop-2-enoic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;98%
1135-24-6

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

108-91-8

cyclohexylamine

(E)-N-cyclohexyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide

Conditions
ConditionsYield
at 85℃; for 0.05h; Microwave irradiation;98%
3731-51-9

(2-aminomethylpyridine)

1135-24-6

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

113985-17-4

(E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-2-ylmethyl)acrylamide

Conditions
ConditionsYield
at 85℃; for 0.05h; Microwave irradiation;98%
3731-53-1

4-(aminomethyl)pyridine

1135-24-6

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

(E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-4-ylmethyl)acrylamide

Conditions
ConditionsYield
at 85℃; for 0.05h; Microwave irradiation;98%
71-23-8

propan-1-ol

1135-24-6

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

59831-93-5

propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-prop-2-enoate

Conditions
ConditionsYield
With sulfuric acid for 6h; Reflux;97%
With sulfuric acid at 107℃; under 1034.32 Torr; for 0.0666667h; Microwave irradiation;94%
With acetyl chloride for 48h;90%
1135-24-6

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

62-53-3

aniline

55882-80-9

3-(4-hydroxy-3-methoxyphenyl)-N-(4-phenyl)prop-(2E)-enamide

Conditions
ConditionsYield
at 125℃; for 0.0833333h; Microwave irradiation;97%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 8h;76%
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 18h;44%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; Inert atmosphere;33%
1135-24-6

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

109-76-2

Trimethylenediamine

157771-76-1

N,N'-(trimethylene)-bis[(E)-3-(4-hydroxy-3-methoxyphenyl)acrylamide]

Conditions
ConditionsYield
at 110℃; for 0.116667h; Microwave irradiation;97%
120-43-4

4-ethoxycarbonylpiperazine

1135-24-6

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

(E)‐ethyl 4‐(3‐(4‐hydroxy‐3‐methoxyphenyl)acryloyl)piperazine‐1‐carboxylate

Conditions
ConditionsYield
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.5h;
Stage #2: 4-ethoxycarbonylpiperazine In N,N-dimethyl-formamide at 20℃;
96.7%
1135-24-6

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

2785-89-9

4-Ethylguaiacol

Conditions
ConditionsYield
With isopropyl alcohol; palladium on activated charcoal Product distribution; Heating;96%
With isopropyl alcohol; palladium on activated charcoal Heating;96%
Multi-step reaction with 2 steps
1: palladium/calcium carbonate; methanol / Hydrogenation
2: soda lime / 280 °C / 20 Torr
View Scheme
1135-24-6

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

106-95-6

allyl bromide

115375-24-1

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

Conditions
ConditionsYield
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid; allyl bromide With potassium carbonate In acetonitrile at 70℃; for 18h; Inert atmosphere;
Stage #2: With potassium hydroxide In methanol; water; acetonitrile at 660℃; for 24h; Inert atmosphere;
96%
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With potassium carbonate In acetone at 20℃; for 0.5h;
Stage #2: allyl bromide In acetone for 48h; Williamson ether synthesis; Reflux;
Stage #3: With sodium hydroxide In ethanol for 2h; Reflux;
84%
1135-24-6

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

107-30-2

chloromethyl methyl ether

(E)-methoxymethyl 3-[3-methoxy-4-(methoxymethoxy)phenyl]acrylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3.5h;96%
3731-52-0

3-Aminomethylpyridine

1135-24-6

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

(E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-3-ylmethyl)acrylamide

Conditions
ConditionsYield
at 85℃; for 0.05h; Microwave irradiation;96%
1135-24-6

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

15356-60-2

(1S,2R,5S)-(+)-menthol

(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl-(E)-3-(4-hydroxy-3-methoxyphenyl) acrylate

Conditions
ConditionsYield
With sulfuric acid-immobilized mesoporous silica catalyst at 70℃; for 1.5h; Green chemistry;96%
1135-24-6

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

474398-83-9

(2E)-3-(4-hydroxy-3-methoxyphenyl)acrylohydrazide

Conditions
ConditionsYield
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 25℃; for 2h;
Stage #2: With hydrazine hydrate In acetonitrile at 0 - 10℃;
96%
1135-24-6

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

18162-48-6

tert-butyldimethylsilyl chloride

854737-54-5

(E)‐3‐(4‐((tert‐butyldimethylsilyl)oxy)‐3‐methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 14h;95%
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With 1H-imidazole In N,N-dimethyl-formamide
Stage #2: tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #3: With potassium carbonate In tetrahydrofuran; methanol; water for 1h;
93%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;67%
1135-24-6

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

86945-25-7

4-(2-aminoethyl)-1-(phenylmethyl)piperidine

(E)-N-(2-(1-benzylpiperidin-4-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

Conditions
ConditionsYield
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 120℃; for 0.116667h; Microwave irradiation; Inert atmosphere; Sealed tube;
Stage #2: 4-(2-aminoethyl)-1-(phenylmethyl)piperidine In tetrahydrofuran at 120℃; for 0.166667h; Microwave irradiation; Inert atmosphere; Sealed tube;
95%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 12h;75%
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  • Ferulic Acid  CAS No.: 1135-24-6

  • Casno:

    1135-24-6

    Ferulic Acid CAS No.: 1135-24-6

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Chemistry

IUPAC Name: (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid 
Empirical Formula: C10H10O4
Molecular Weight: 194.184g/mol
EINECS: 208-679-7 
Structure of 4-Hydroxy-3-methoxycinnamic acid (CAS NO.1135-24-6):

Index of Refraction: 1.626
Molar Refractivity: 52.26 cm3
Molar Volume: 147.4 cm3
Polarizability: 20.72×10-24cm3
Surface Tension: 56.1 dyne/cm
Density: 1.316 g/cm3
Flash Point: 150.5 °C
Enthalpy of Vaporization: 65.35 kJ/mol 
Melting Point: 168-172 °C(lit.)
Boiling Point: 372.3 °C at 760 mmHg
Vapour Pressure: 3.34E-06 mmHg at 25°C 
Water Solubility: soluble 
Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Cinnamic Acids, Esters and Derivatives;Aromatics 
Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)O)O
Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)O)O
InChI: InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
InChIKey: KSEBMYQBYZTDHS-HWKANZROSA-N

Uses

1.It is an antioxidant in the sense that it is reactive toward free radicals such as reactive oxygen species (ROS). ROS and free radicals are implicated in DNA damage, cancer, accelerated cell aging.
2.It may have pro-apoptotic effects in cancer cells, thereby leading to their destruction.
3.It may be effective at preventing cancer induced by exposure to the carcinogenic compounds benzopyreneand 4-nitroquinoline 1-oxide.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD intraperitoneal > 350mg/kg (350mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: REGIDITY
Indian Journal of Pharmaceutical Sciences. Vol. 49, Pg. 77, 1987.
mouse LD50 intravenous 857mg/kg (857mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 38, Pg. 1620, 1990.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: UD3365500
Hazard Note: Irritant
Hazardous Substances Data: 1135-24-6(Hazardous Substances Data)

Specification

  4-Hydroxy-3-methoxycinnamic acid , its cas register number is 1135-24-6. It also can be called 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid ; 3-Methoxy-4-hydroxycinnamic acid ; 4-Hydroxy-3-methoxy cinnamic acid ; CCRIS 3256 ; Cinnamic acid, 4-hydroxy-3-methoxy- ; Coniferic acid ; Ferulic acid .
 4-Hydroxy-3-methoxycinnamic acid (CAS NO.1135-24-6) is a pale yellow solid.

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