| Identification | More | [Name]
4-Hydroxycinnamic acid | [CAS]
501-98-4 | [Synonyms]
3-(4-HYDROXYPHENYL)ACRYLIC ACID
4-COUMARIC ACID
4-HYDROXYCINNAMIC ACID
AKOS 221-47
AKOS BAR-2479
COUMARIC ACID, TRANS-P-
LABOTEST-BB LT00452637
P-COUMARIC ACID
P-CUMARIC ACID
PHCA
P-HYDROXYCINNAMIC ACID
P-HYDROXYL CINNAMIC ACID
RARECHEM BK HW 0163
TRANS-4-COUMARIC ACID
TRANS-4-HYDROXYCINNAMIC ACID
TRANS-P-COUMARIC ACID
TRANS-P-CUMARIC ACID
(e)-3-(4-hydroxyphenyl)-2-propenoicacid
(E)-p-Coumaric acid
(e)-p-coumaricacid | [EINECS(EC#)]
231-000-0 | [Molecular Formula]
C9H8O3 | [MDL Number]
MFCD00004399 | [Molecular Weight]
164.16 | [MOL File]
501-98-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white to beige or greenish powder | [Melting point ]
214 °C (dec.)(lit.)
| [Boiling point ]
231.61°C (rough estimate) | [density ]
1.1403 (rough estimate) | [refractive index ]
1.4500 (estimate) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
ethanol: soluble50mg/mL | [form ]
Powder | [pka]
4.65±0.10(Predicted) | [color ]
Off-white to beige or greenish | [Odor]
at 100.00?%. balsamic | [Water Solubility ]
soluble | [Merck ]
14,2560 | [BRN ]
2207383 | [Stability:]
Light Sensitive | [InChIKey]
NGSWKAQJJWESNS-ZZXKWVIFSA-N | [LogP]
1.460 | [CAS DataBase Reference]
501-98-4(CAS DataBase Reference) | [NIST Chemistry Reference]
p-Hydroxycinnamic acid(501-98-4) | [EPA Substance Registry System]
501-98-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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 ]
2
| [RTECS ]
GD9095000
| [HS Code ]
29163990 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white to beige or greenish powder | [Uses]
trans-p-Coumaric Acid(501-98-4) is the E-isomer of p-Coumaric Acid (C755365), a hydroxy derivative of Cinnamic Acid with antioxidant properties. p-Coumaric acid is a is a major component of lignocellulose. Stud
ies suggest that p-Coumaric Acid may reduce the risk of cancer by reducing the formation of carcinogenic nitrosamines.
| [Application]
p-Coumaric acid has been used as a component of chemiluminescent substrate for protein detection in western blotting. | [Definition]
ChEBI: The trans-isomer of 4-coumaric acid. | [Preparation]
Synthesis of p-Coumaric acid: take o-acetylsalicyloyl chloride as raw material, in the presence of magnesium chloride, react with diethyl malonate in acetonitrile solvent, then add triethylamine, and react at 0°C for 1 h to obtain ( 2-acetoxybenzoyl) diethyl malonate product, then heated to 50°C in potassium hydroxide/methanol solution, reacted for 3h, and cyclized to obtain p-Coumaric acid. | [Biochem/physiol Actions]
p-Coumaric acid is mainly a plant metabolite which exhibits antioxidant and anti-inflammatory properties. It also shows bactericidal activity by damaging bacterial cell membrane and by interacting with bacterial DNA. In western blot, p-coumaric is also used as an enhancer in chemiluminescent substrate.
Hydroxycinnamic acid found in many fruits and vegetables. | [Purification Methods]
Crystallise p-coumaric acid from H2O (charcoal). It forms needles from concentrated aqueous solutions as the anhydrous acid, but from hot dilute solutions the monohydrate acid separates on slow cooling. The acid (33g) has been crystallised from 2.5L of H2O (1.5g charcoal) yielding 28.4g of recrystallised acid, m 207o. It is insoluble in *C6H6 or pet ether. The UV in 95% EtOH has max 223 and 286nm ( 14,450 and 19000 M-1cm-1). [UV Wheeler & Covarrubias J Org Chem 28 2015 1963, Corti Helv Chim Acta 32 681 1949, Beilstein 10 IV 1005.] |
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