Product Name

  • Name

    p-Hydroxy-cinnamic acid

  • EINECS 231-000-0
  • CAS No. 7400-08-0
  • Article Data284
  • CAS DataBase
  • Density 1.33 g/cm3
  • Solubility
  • Melting Point 212-214 °C
  • Formula C9H8O3
  • Boiling Point 346.052 °C at 760 mmHg
  • Molecular Weight 164.161
  • Flash Point 177.284 °C
  • Transport Information
  • Appearance Light yellow to beige crystalline powder
  • Safety 26-36-36/37/39-22
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 7400-08-0 (p-Hydroxy-cinnamic acid)
  • Hazard Symbols IrritantXi
  • Synonyms Cinnamicacid, p-hydroxy-(8CI);3-(4-Hydroxyphenyl)-2-propenoic acid;3-(4-Hydroxyphenyl)acrylic acid;4-Coumaric acid;
  • PSA 57.53000
  • LogP 1.49000

Synthetic route

malonic acid
141-82-2

malonic acid

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With piperidine; pyridine for 1h; Knoevenagel-Doebner-Stobbe Reaction; Reflux;98%
With ammonium acetate for 0.05h; Irradiation;97%
With aluminum oxide; lithium chloride for 0.0833333h; Doebner condensation; microwave irradiation;97%
(E)-4-iodocinnamic acid
113641-76-2

(E)-4-iodocinnamic acid

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide In water at 100℃; for 6h;88%
5-O-(E)-p-coumaroylquinic acid ethyl ester
1443678-33-8

5-O-(E)-p-coumaroylquinic acid ethyl ester

A

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

B

D-(-)-quinic acid
77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h;A n/a
B 2.5 mg
2'-O-acetyl-3-O-(E)-p-coumaroylsucrose

2'-O-acetyl-3-O-(E)-p-coumaroylsucrose

A

D-Fructose
57-48-7

D-Fructose

B

D-glucose
50-99-7

D-glucose

C

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h;
3',6'-di-O-acetyl-3-O-(E)-p-coumaroylsucrose

3',6'-di-O-acetyl-3-O-(E)-p-coumaroylsucrose

A

D-Fructose
57-48-7

D-Fructose

B

D-glucose
50-99-7

D-glucose

C

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h;
4,2',3',6'-tetra-O-acetyl-3-O-(E)-p-coumaroylsucrose
1446205-86-2

4,2',3',6'-tetra-O-acetyl-3-O-(E)-p-coumaroylsucrose

A

D-Fructose
57-48-7

D-Fructose

B

D-glucose
50-99-7

D-glucose

C

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h;
1,2',3',4',6'-penta-O-acetyl-3-O-(E)-p-coumaroylsucrose
1392307-46-8

1,2',3',4',6'-penta-O-acetyl-3-O-(E)-p-coumaroylsucrose

A

D-Fructose
57-48-7

D-Fructose

B

D-glucose
50-99-7

D-glucose

C

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h;
para-coumaric acid
7400-08-0

para-coumaric acid

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With iodine In d(4)-methanol at 50℃; for 0.166667h; Time; Green chemistry;
4-Iodophenol
540-38-5

4-Iodophenol

acrylic acid
79-10-7

acrylic acid

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In water at 80℃; for 2h;94%
With potassium carbonate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere;93%
With tetrakis(triphenylphosphine) palladium(0); lithium chloride; potassium hydroxide In water at 85℃; for 3h; Heck Reaction;95 %Chromat.
L-tyrosine
60-18-4

L-tyrosine

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
Einw. von Bacillus proteus vulgaris in Ringerscher Loesung;
With 1,3-bis[tris(hydroxymethyl)methylamino]-propane; Arabidopsis thaliana phenylalanine ammonia lyase 1 In water at 37℃; pH=8.4; Enzyme kinetics; Further Variations:; Reagents;
free cell extract of Rhodotorula rubra (ATCC 889) In Tris-HCl buffer pH=8.5; Kinetics; Enzymatic reaction;
kaempferol 3-O-{[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl(1→2)]-α-L-rhamnopyranosyl(1→6)}-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside

kaempferol 3-O-{[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl(1→2)]-α-L-rhamnopyranosyl(1→6)}-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness;
quercetin 3-O-[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl(1→2)]-β-D-galactopyranoside-7-O-(2-O-E-caffeoyl)-β-D-glucuropyranoside

quercetin 3-O-[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl(1→2)]-β-D-galactopyranoside-7-O-(2-O-E-caffeoyl)-β-D-glucuropyranoside

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness;
quercetin 3-O-[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl-(1→2)]-β-D-galactopyranoside-7-O-β-D-glucuropyranoside

quercetin 3-O-[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl-(1→2)]-β-D-galactopyranoside-7-O-β-D-glucuropyranoside

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness;
kaempferol 3-O-[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl-(1→2)]-β-D-galactopyranoside-7-O-β-D-glucuropyranoside

kaempferol 3-O-[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl-(1→2)]-β-D-galactopyranoside-7-O-β-D-glucuropyranoside

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness;
juglanoside J

juglanoside J

A

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

B

(1S)-1,2,3,4-tetrahydro-8-hydroxy-4-oxonaphthalen-1-yl 6-O-[(3,4,5-trihydroxyphenyl)carbonyl]-β-D-glucopyranoside

(1S)-1,2,3,4-tetrahydro-8-hydroxy-4-oxonaphthalen-1-yl 6-O-[(3,4,5-trihydroxyphenyl)carbonyl]-β-D-glucopyranoside

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 6h;A 1.5 mg
B 2.8 mg
4-bromo-phenol
106-41-2

4-bromo-phenol

acrylic acid
79-10-7

acrylic acid

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sodium carbonate; palladium dichloride In water at 100℃; for 2h;65%
With sodium carbonate; palladium dichloride at 100℃; for 2h;65%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With hydrogenchloride; malonic acid; aniline In pyridine
1-O-(E)-caffeoyl-2-O-p-(E)-coumaroyl-β-D-glucopyranose

1-O-(E)-caffeoyl-2-O-p-(E)-coumaroyl-β-D-glucopyranose

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With hydrogenchloride; water at 90℃; for 3h; Sealed tube;
methyl 4-hydroxycinnamate
3943-97-3

methyl 4-hydroxycinnamate

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 20℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox;92%
peonidin 3-O-[2-O-(2-O-(trans-sinapoyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]

peonidin 3-O-[2-O-(2-O-(trans-sinapoyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]

A

D-Glucose
2280-44-6

D-Glucose

B

malonic acid
141-82-2

malonic acid

C

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

D

trans-3,5-dimethoxy-4-hydroxycinnamic acid
530-59-6

trans-3,5-dimethoxy-4-hydroxycinnamic acid

E

peonidin chloride
134-01-0

peonidin chloride

Conditions
ConditionsYield
With hydrogenchloride; water at 100℃; for 1h;
cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]

cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]

A

D-Glucose
2280-44-6

D-Glucose

B

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

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

C

malonic acid
141-82-2

malonic acid

D

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

E

cyanidin chloride
528-58-5

cyanidin chloride

Conditions
ConditionsYield
With hydrogenchloride; water at 100℃; for 1h;
peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]

peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]

A

D-Glucose
2280-44-6

D-Glucose

B

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

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

C

malonic acid
141-82-2

malonic acid

D

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

E

peonidin chloride
134-01-0

peonidin chloride

Conditions
ConditionsYield
With hydrogenchloride; water at 100℃; for 1h;
allivictoside C

allivictoside C

A

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

B

kaempferol 3,7,4'-tri-O-β-D-glucopyranoside

kaempferol 3,7,4'-tri-O-β-D-glucopyranoside

Conditions
ConditionsYield
With potassium hydroxide at 20℃; for 12h;
allivictoside E

allivictoside E

A

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

B

kaempferol 3,7,4'-tri-O-β-D-glucopyranoside

kaempferol 3,7,4'-tri-O-β-D-glucopyranoside

Conditions
ConditionsYield
With potassium hydroxide at 20℃; for 12h;
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In methanol under 760 Torr; Ambient temperature;100%
With hydrogen; palladium on activated charcoal In methanol100%
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃;99%
methanol
67-56-1

methanol

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

methyl 4-hydroxycinnamate
3943-97-3

methyl 4-hydroxycinnamate

Conditions
ConditionsYield
With sulfuric acid for 24h; Reflux;100%
With sulfuric acid for 7h; Heating;99%
With sulfuric acid for 24h; Reflux;99%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

acetic anhydride
108-24-7

acetic anhydride

4-acetoxycinnamic acid
27542-85-4

4-acetoxycinnamic acid

Conditions
ConditionsYield
With pyridine at 20℃;100%
With pyridine; dmap for 1.5h;97%
With pyridine at 25℃; for 24h;95%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

dimethyl sulfate
77-78-1

dimethyl sulfate

3-(4-methoxy-phenyl)acrylic acid methyl ester
3901-07-3

3-(4-methoxy-phenyl)acrylic acid methyl ester

Conditions
ConditionsYield
Stage #1: p-Coumaric Acid With potassium carbonate In acetone at 20℃; for 0.25h;
Stage #2: dimethyl sulfate In acetone at 20℃; for 8h; Heating / reflux;
99%
With potassium carbonate In acetone at 25℃; for 24h;92%
With potassium carbonate In acetone for 3h; Reflux;68%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

4-hydroxycinnamic acid N-hydroxysuccinimide ester
88492-43-7

4-hydroxycinnamic acid N-hydroxysuccinimide ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;95%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 18h; Ambient temperature;59%
With diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 2h;58%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(E)-3-(4'-((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid
141222-28-8

(E)-3-(4'-((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 2h;100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h;98%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h;98%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

trans-p-coumaric acid-4-O-sulfate

trans-p-coumaric acid-4-O-sulfate

Conditions
ConditionsYield
With sulfur trioxide trimethylamine complex; sodium hydrogencarbonate; sodium hydroxide In water at 20℃; for 96h;99%
With chlorosulfonic acid In pyridine at 20℃;63%
With D-glucose; aryl sulfotransferase SULT1A1 Rattus norvegicus; isopropyl β-D-thiogalactopyranoside for 96h; Reagent/catalyst; Enzymatic reaction;
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

methyl 4-hydroxycinnamate
3943-97-3

methyl 4-hydroxycinnamate

Conditions
ConditionsYield
With sulfuric acid In methanol Heating / reflux;98%
With sulfuric acid In methanol; ethanol; water61%
With methanol; sulfuric acid
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

4-Vinylphenol
2628-17-3

4-Vinylphenol

Conditions
ConditionsYield
With 4-methoxy-phenol In water; N,N-dimethyl-formamide at 150℃; for 4h; Solvent;97%
With 1-methyl-1H-imidazole; sodium hydrogencarbonate for 0.333333h; Heating; microwave irradiation;94%
With bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate; potassium acetate In DMF (N,N-dimethyl-formamide) at 150℃; for 1.5h; Product distribution / selectivity;94%
4-benzylpyperidine
31252-42-3

4-benzylpyperidine

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

(E)-1-(4-benzylpiperidin-1-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

(E)-1-(4-benzylpiperidin-1-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;56.5%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;47.7%
Stage #1: p-Coumaric Acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 0.5h; Condensation;
Stage #2: 4-benzylpyperidine In tetrahydrofuran at 20℃; Acylation;
19%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

hydroxytyrosol
10597-60-1

hydroxytyrosol

(2E)-3-(4-hydroxyphenyl)-2-propenoic acid 2-(3,4-dihydroxyphenyl)ethyl ester

(2E)-3-(4-hydroxyphenyl)-2-propenoic acid 2-(3,4-dihydroxyphenyl)ethyl ester

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 48h;73%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; Mitsunobu Displacement; chemoselective reaction;66%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; Schlenk technique; Inert atmosphere;54%
With Escherichia coli strain B-CP1 at 30℃; for 24h; Microbiological reaction; Enzymatic reaction;
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

benzyl bromide
100-39-0

benzyl bromide

(E)-4-benzyloxycinnamic acid
6272-45-3

(E)-4-benzyloxycinnamic acid

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide92%
With potassium carbonate In acetone for 12h; Reflux;92%
With sodium hydroxide In ethanol82%
With potassium hydroxide In ethanol; water at 20℃; for 72h;41%
With sodium hydroxide
ethanol
64-17-5

ethanol

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

ethyl (E)-4-hydroxycinnamate
2979-06-8, 7361-92-4, 7362-39-2

ethyl (E)-4-hydroxycinnamate

Conditions
ConditionsYield
With sulfuric acid at 60℃;100%
With sulfuric acid at 65℃; for 18h;95%
With hydrogenchloride92%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

(E)-3-(4-hydroxyphenyl)acryloylhydrazide
90557-60-1

(E)-3-(4-hydroxyphenyl)acryloylhydrazide

Conditions
ConditionsYield
Stage #1: p-Coumaric 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℃;
79%
Stage #1: p-Coumaric Acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 2h;
Stage #2: With hydrazine hydrate In acetonitrile; cyclohexene at 0 - 10℃;
46%
Stage #1: p-Coumaric Acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 2h;
Stage #2: With hydrazine; cyclohexene In acetonitrile at 0 - 20℃; for 1.33333h;
36%
Multi-step reaction with 2 steps
1: 74 percent / Et3N / ethyl acetate / 6 h / Heating
2: 55 percent / N2H4 / CHCl3 / Heating
View Scheme
1,2,3,4-tetrahydroisoquinoline
91-21-4

1,2,3,4-tetrahydroisoquinoline

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

(E)-1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

(E)-1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;76.7%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;62.7%
2-phenylethanol
60-12-8

2-phenylethanol

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

(2E)-3-(4-hydroxyphenyl)-2-propenoic acid 2-phenylethyl ester

(2E)-3-(4-hydroxyphenyl)-2-propenoic acid 2-phenylethyl ester

Conditions
ConditionsYield
With ytterbium(III) triflate In nitromethane at 120℃; for 1h;70.6%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 48h;40%
With Escherichia coli strain B-CP1 at 30℃; for 24h; Microbiological reaction; Enzymatic reaction;
O-2-tetrahydro-2H-pyranhydroxylamine
6723-30-4

O-2-tetrahydro-2H-pyranhydroxylamine

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

(E)-3-(4-hydroxyphenyl)-N-((tetrahydro-2H-pyran-2-yl)oxy)acrylamide

(E)-3-(4-hydroxyphenyl)-N-((tetrahydro-2H-pyran-2-yl)oxy)acrylamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;84%
propan-1-ol
71-23-8

propan-1-ol

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

(E)-propyl 3-(4-hydroxyphenyl)acrylate
94530-69-5

(E)-propyl 3-(4-hydroxyphenyl)acrylate

Conditions
ConditionsYield
With sulfuric acid for 3h;72%
With dmap; dicyclohexyl-carbodiimide at 50℃; for 24h;71%
With sulfuric acid Reflux;58.43%
16%
With sulfuric acid
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

ethoxymethyl 4-hydroxycinnamate
642471-45-2

ethoxymethyl 4-hydroxycinnamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;84%
With triethylamine In dichloromethane at 0℃;84%
6-chloro-1-hexanol
2009-83-8

6-chloro-1-hexanol

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

4-(6-hydroxyhexyloxy)cinnamic acid
503000-67-7

4-(6-hydroxyhexyloxy)cinnamic acid

Conditions
ConditionsYield
Stage #1: p-Coumaric Acid With potassium hydroxide; potassium iodide In ethanol; water for 0.166667h;
Stage #2: 6-chloro-1-hexanol In ethanol; water at 30 - 40℃; Heating / reflux;
62%
With 1,3-dimethyl-2-imidazolidinone; potassium carbonate; potassium iodide at 130℃; for 17h;47%
Stage #1: p-Coumaric Acid With potassium iodide; potassium hydroxide In ethanol; water for 0.166667h; Reflux;
Stage #2: 6-chloro-1-hexanol In ethanol; water for 48h; Reflux;
Stage #3: With hydrogenchloride In ethanol; water
46.8%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

4-methoxy-aniline
104-94-9

4-methoxy-aniline

C16H15NO3

C16H15NO3

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide for 6h;85%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 23℃; for 24h;78.5%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Carvacryl chloroacetate

Carvacryl chloroacetate

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With triethylamine; potassium iodide In N,N-dimethyl-formamide at 20℃; for 24h;80%
1-phenylmethylpiperazine
2759-28-6

1-phenylmethylpiperazine

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

(E)-1-(4-benzylpiperazin-1-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

(E)-1-(4-benzylpiperazin-1-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;63.7%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

hydroxymethylparthenolide
93930-15-5

hydroxymethylparthenolide

((1aR,7aS,10aS,10bS,E)-1a-methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-decahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-5-yl)methyl (E)-3-(4-hydroxyphenyl)acrylate

((1aR,7aS,10aS,10bS,E)-1a-methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-decahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-5-yl)methyl (E)-3-(4-hydroxyphenyl)acrylate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere;76%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; Cooling with ice;69%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

hexan-1-ol
111-27-3

hexan-1-ol

trans-hexyl 3-(4-hydroxyphenyl)propenoate

trans-hexyl 3-(4-hydroxyphenyl)propenoate

Conditions
ConditionsYield
Stage #1: p-Coumaric Acid; hexan-1-ol In tetrahydrofuran at 0℃; for 0.5h; Mitsunobu Displacement;
Stage #2: With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu Displacement;
36.88%
With di-isopropyl azodicarboxylate; triphenylphosphine In N,N-dimethyl-formamide for 12h; Ambient temperature;15 mg

4-Hydroxycinnamic acid Chemical Properties

IUPAC Name: (E)-3-(4-Hydroxyphenyl)prop-2-enoic acid
Synonyms of 4-Coumaric acid (CAS NO.7400-08-0): 3-(4-Hydroxyphenyl)-2-propenoic acid ; 4-Hydroxycinnamic acid ; Hydroxycinnamic acid ; beta-(4-Hydroxyphenyl)acrylic acid ; p-Hydroxyphenylacrylic acid ; 2-Propenoic acid, 3-(4-hydroxyphenyl)-
CAS NO: 7400-08-0
Molecular Formula: C9H8O3
Molecular Weight: 164.16
Molecular Structure:
EINECS: 231-000-0
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 3
Polar Surface Area: 35.53 Å2
Index of Refraction: 1.66
Molar Refractivity: 45.58 cm3
Molar Volume: 123.4 cm3
Surface Tension: 62.4 dyne/cm
Density: 1.329 g/cm3
Flash Point: 177.3 °C
Enthalpy of Vaporization: 62.28 kJ/mol
Boiling Point: 346.1 °C at 760 mmHg
Vapour Pressure: 2.24E-05 mmHg at 25°C
Melting point: 212-214°C
Appearance: Light yellow to beige crystalline powder
SMILES: O=C(O)/C=C/c1ccc(O)cc1
InChI: InChI=1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
InChIKey: NGSWKAQJJWESNS-ZZXKWVIFBJ
Std. InChI: InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
Std. InChIKey: NGSWKAQJJWESNS-ZZXKWVIFSA-N
Product Categories of 4-Coumaric acid (CAS NO.7400-08-0): Cinnamic acid

4-Hydroxycinnamic acid Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 657mg/kg (657mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 104, Pg. 793, 1984.

4-Hydroxycinnamic acid Consensus Reports

Reported in EPA TSCA Inventory.

4-Hydroxycinnamic acid Safety Profile

Safety Information of 4-Coumaric acid (CAS NO.7400-08-0):
Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39-22
S22: Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 2
RTECS: GD9095000
Moderately toxic by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and fumes. See also COUMARIN

4-Hydroxycinnamic acid Specification

Stability and Reactivity :
Chemical Stability: Stable under normal temperatures and pressures. 
Conditions to Avoid: Incompatible materials. 
Incompatibilities with Other Materials Strong oxidizing agents. 
Hazardous Decomposition Products Carbon monoxide, carbon dioxide. 
Hazardous Polymerization Has not been reported. 
First Aid Measures:
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.  Ingestion: Get medical aid. Wash mouth out with water. 
Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. 
Notes to Physician: Treat symptomatically and supportively.  
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation. 
Storage: Store in a cool, dry place. Store in a tightly closed container.

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