501-98-4 Usage
Chemical Properties
Off-white to beige or greenish powder. Soluble in alcohol, ether and hot water, slightly soluble in benzene, insoluble in petroleum ether.
Uses
trans-p-Coumaric Acid 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.
Definition
ChEBI: p-coumaric acid is the trans-isomer of 4-coumaric acid. 4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate.
Application
trans-4-Hydroxycinnamic acid is used as a hydroxycinnamic acid with antioxidant properties. p-Coumaric acid is an aromatic phytochemical for proteomics research. It has been used as a component of chemiluminescent substrate for protein detection in western blotting.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 501-98-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 1 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 501-98:
(5*5)+(4*0)+(3*1)+(2*9)+(1*8)=54
54 % 10 = 4
So 501-98-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O3/c1-6(9(11)12)7-2-4-8(10)5-3-7/h2-5,10H,1H2,(H,11,12)
501-98-4Relevant articles and documents
Understanding the role played by protic ionic liquids (PILs) and the substituent effect for enhancing the generation of: Z-cinnamic acid derivatives
Rodríguez, Roció B.,Rodríguez, Roció B.,Zapata, Ramiro L.,Salum, Mariá L.,Salum, Mariá L.,Erra-Balsells, Rosa,Erra-Balsells, Rosa
, p. 819 - 830 (2020/07/03)
Photoisomerization of a series of substituted E-cinnamic acids in MeCN in their acid forms and as their corresponding protic ionic liquids (PILs) with light of 300 nm is studied. The nature, strength, number, and position effects of substituents on the photochemical behavior of E-cinnamic derivatives are investigated. The photosensitization of the reaction in the presence of Michler's ketone is also studied at 366 nm and it demonstrates that the triplet-excited state is involved in the reaction. As the presence of n-butylamine needed to form the PILs significantly increases the photoproduct yields in all cases, the role of the PILs is also discussed. Thus, understanding of these fundamental aspects has allowed us to establish an excellent and practical synthetic protocol for successfully synthesizing Z-cinnamic acids. This journal is
Flavonoid glycosides from Sedum bulbiferum
Warashina, Tsutomu,Miyase, Toshio
, p. 1199 - 1204 (2017/12/26)
The MeOH extract from dried whole Sedum bulbiferum MAKINO (Crassulaceae) plants yielded 34 compounds, including six new flavonoid glycosides and 28 known compounds. The structures of new compounds were established using NMR, Mass spectroscopic analysis an
Phenolic glycosides from the twigs of Salix glandulosa
Kim, Chung Sub,Kwon, Oh Wook,Kim, Sun Yeou,Choi, Sang Un,Kim, Jae Yoon,Han, Ji Young,Choi, Soo Im,Choi, Jong Gil,Kim, Ki Hyun,Lee, Kang Ro
, p. 1955 - 1961 (2014/10/16)
As a part of an ongoing search for bioactive constituents from Korean medicinal plants, the phytochemical investigations of the twigs of Salix glandulosa afforded 12 new phenolic glycosides (1-12) and a known analogue (13). The structures of 1-13 were characterized by a combination of NMR methods (1H and 13C NMR, 1H-1H COSY, HMQC, and HMBC), chemical hydrolysis, and GC/MS. The absolute configuration of 13 [(1R,2S)-2-hydroxycyclohexyl-2′-O-trans-p-coumaroyl-β-d- glucopyranoside] was determined for the first time. Compounds 1-3, 6, and 7 exhibited inhibitory effects on nitric oxide production in lipopolysaccharide- activated murine microglial cells (IC50 values in the range 6.6-20.5 μM).
