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| CAS No.: | 7400-08-0 |
|---|---|
| Name: | p-Hydroxy-cinnamic acid |
| Article Data: | 284 |
| Molecular Structure: | |
|
|
|
| Formula: | C9H8O3 |
| Molecular Weight: | 164.161 |
| Synonyms: | Cinnamicacid, p-hydroxy-(8CI);3-(4-Hydroxyphenyl)-2-propenoic acid;3-(4-Hydroxyphenyl)acrylic acid;4-Coumaric acid; |
| EINECS: | 231-000-0 |
| Density: | 1.33 g/cm3 |
| Melting Point: | 212-214 °C |
| Boiling Point: | 346.052 °C at 760 mmHg |
| Flash Point: | 177.284 °C |
| Appearance: | Light yellow to beige crystalline powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36-36/37/39-22 |
| PSA: | 57.53000 |
| LogP: | 1.49000 |
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| 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% |
- 113641-76-2
(E)-4-iodocinnamic acid
- 7400-08-0
p-Coumaric Acid
| Conditions | Yield |
|---|---|
| With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide In water at 100℃; for 6h; | 88% |
- 1443678-33-8
5-O-(E)-p-coumaroylquinic acid ethyl ester
A
- 7400-08-0
p-Coumaric Acid
B
- 77-95-2
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; |
- 1446205-86-2
4,2',3',6'-tetra-O-acetyl-3-O-(E)-p-coumaroylsucrose
A
- 57-48-7
D-Fructose
B
- 50-99-7
D-glucose
C
- 7400-08-0
p-Coumaric Acid
| Conditions | Yield |
|---|---|
| With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h; |
- 1392307-46-8
1,2',3',4',6'-penta-O-acetyl-3-O-(E)-p-coumaroylsucrose
A
- 57-48-7
D-Fructose
B
- 50-99-7
D-glucose
C
- 7400-08-0
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; |
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Chemistry
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
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. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
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
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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