Conditions | Yield |
---|---|
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
p-Coumaric Acid
Conditions | Yield |
---|---|
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
A
p-Coumaric Acid
B
D-(-)-quinic acid
Conditions | Yield |
---|---|
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h; | A n/a B 2.5 mg |
Conditions | Yield |
---|---|
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h; |
Conditions | Yield |
---|---|
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h; |
4,2',3',6'-tetra-O-acetyl-3-O-(E)-p-coumaroylsucrose
A
D-Fructose
B
D-glucose
C
p-Coumaric Acid
Conditions | Yield |
---|---|
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
A
D-Fructose
B
D-glucose
C
p-Coumaric Acid
Conditions | Yield |
---|---|
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h; |
Conditions | Yield |
---|---|
With iodine In d(4)-methanol at 50℃; for 0.166667h; Time; Green chemistry; |
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
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; |
p-Coumaric Acid
Conditions | Yield |
---|---|
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness; |
p-Coumaric Acid
Conditions | Yield |
---|---|
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness; |
p-Coumaric Acid
Conditions | Yield |
---|---|
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness; |
p-Coumaric Acid
Conditions | Yield |
---|---|
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness; |
A
p-Coumaric Acid
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; for 6h; | A 1.5 mg B 2.8 mg |
Conditions | Yield |
---|---|
With sodium carbonate; palladium dichloride In water at 100℃; for 2h; | 65% |
With sodium carbonate; palladium dichloride at 100℃; for 2h; | 65% |
Conditions | Yield |
---|---|
With hydrogenchloride; malonic acid; aniline In pyridine |
p-Coumaric Acid
Conditions | Yield |
---|---|
With hydrogenchloride; water at 90℃; for 3h; Sealed tube; |
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 20℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox; | 92% |
A
D-Glucose
B
malonic acid
C
p-Coumaric Acid
D
trans-3,5-dimethoxy-4-hydroxycinnamic acid
E
peonidin chloride
Conditions | Yield |
---|---|
With hydrogenchloride; water at 100℃; for 1h; |
A
D-Glucose
B
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
C
malonic acid
D
p-Coumaric Acid
E
cyanidin chloride
Conditions | Yield |
---|---|
With hydrogenchloride; water at 100℃; for 1h; |
A
D-Glucose
B
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
C
malonic acid
D
p-Coumaric Acid
E
peonidin chloride
Conditions | Yield |
---|---|
With hydrogenchloride; water at 100℃; for 1h; |
Conditions | Yield |
---|---|
With potassium hydroxide at 20℃; for 12h; |
Conditions | Yield |
---|---|
With potassium hydroxide at 20℃; for 12h; |
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide In methanol under 760 Torr; Ambient temperature; | 100% |
With hydrogen; palladium on activated charcoal In methanol | 100% |
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; | 99% |
Conditions | Yield |
---|---|
With sulfuric acid for 24h; Reflux; | 100% |
With sulfuric acid for 7h; Heating; | 99% |
With sulfuric acid for 24h; Reflux; | 99% |
Conditions | Yield |
---|---|
With pyridine at 20℃; | 100% |
With pyridine; dmap for 1.5h; | 97% |
With pyridine at 25℃; for 24h; | 95% |
p-Coumaric Acid
dimethyl sulfate
3-(4-methoxy-phenyl)acrylic acid methyl ester
Conditions | Yield |
---|---|
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
p-Coumaric Acid
4-hydroxycinnamic acid N-hydroxysuccinimide ester
Conditions | Yield |
---|---|
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
tert-butyldimethylsilyl chloride
(E)-3-(4'-((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With sulfuric acid In methanol Heating / reflux; | 98% |
With sulfuric acid In methanol; ethanol; water | 61% |
With methanol; sulfuric acid |
Conditions | Yield |
---|---|
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
p-Coumaric Acid
Conditions | Yield |
---|---|
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
hydroxytyrosol
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide | 92% |
With potassium carbonate In acetone for 12h; Reflux; | 92% |
With sodium hydroxide In ethanol | 82% |
With potassium hydroxide In ethanol; water at 20℃; for 72h; | 41% |
With sodium hydroxide |
ethanol
p-Coumaric Acid
ethyl (E)-4-hydroxycinnamate
Conditions | Yield |
---|---|
With sulfuric acid at 60℃; | 100% |
With sulfuric acid at 65℃; for 18h; | 95% |
With hydrogenchloride | 92% |
p-Coumaric Acid
(E)-3-(4-hydroxyphenyl)acryloylhydrazide
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; | 84% |
Conditions | Yield |
---|---|
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
ethyl chloromethyl ether
ethoxymethyl 4-hydroxycinnamate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 84% |
With triethylamine In dichloromethane at 0℃; | 84% |
6-chloro-1-hexanol
p-Coumaric Acid
4-(6-hydroxyhexyloxy)cinnamic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With triethylamine; potassium iodide In N,N-dimethyl-formamide at 20℃; for 24h; | 80% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 63.7% |
p-Coumaric Acid
hydroxymethylparthenolide
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 |
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
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. |
Reported in EPA TSCA Inventory.
Safety Information of 4-Coumaric acid (CAS NO.7400-08-0):
Hazard Codes: Xi
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
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.
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View