P-Coumaric acid | CAS#501-98-4 | Antioxidant/anti-inflammatory agent

MedKoo Cat#: 464751 | Name: P-Coumaric acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

P-Coumaric acid

CAS#501-98-4

Theoretical Analysis

MedKoo Cat#: 464751

Name: P-Coumaric acid

CAS#: 501-98-4

Chemical Formula: C9H8O3

Exact Mass: 164.0473

Molecular Weight: 164.16

Elemental Analysis: C, 65.85; H, 4.91; O, 29.24

Price and Availability

Size	Price	Availability	Quantity
5g	USD 450.00	2 Weeks
25g	USD 950.00	2 Weeks

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Synonym

P-Coumaric acid; PCoumaric acid; P Coumaric acid;

IUPAC/Chemical Name

(E)-3-(4-hydroxyphenyl)acrylic acid

InChi Key

NGSWKAQJJWESNS-ZZXKWVIFSA-N

InChi Code

InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+

SMILES Code

OC1=CC=C(/C=C/C(O)=O)C=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

p-Coumaric acid is the abundant isomer of cinnamic acid which has antitumor and anti-mutagenic activities.

In vitro activity:

Antiproliferative test showed p-Coumaric acid has an inhibitory effect on HCT 15 and HT 29 cells with an IC₅₀ (concentration for 50% inhibition) value of 1400 and 1600 μmol/L respectively. Colony forming assay revealed the time-dependent inhibition of HCT 15 and HT 29 cells subjected to p-Coumaric acid treatment. Propidium iodide staining of treated HCT 15 cells showed increasing accumulation of apoptotic cells (37.45 ± 1.98 vs 1.07 ± 1.01) at sub-G1 phase of the cell cycle after p-Coumaric acid treatment. Reference: World J Gastroenterol. 2013 Nov 21;19(43):7726-34. https://pubmed.ncbi.nlm.nih.gov/24282361/

In vivo activity:

To test this hypothesis, C57BL/6 male mice were randomly assigned to three groups and fed low-fat (LF) diet (11% calories from fat), high-fat (HF) diet (60% calories from fat, 0.2% cholesterol) with sucrose drink (20% sucrose, HFHS), or HFHS diet with PCA treatment (HFHS+PCA, 50 mg/kg body weight, intraperitoneally) for 13 weeks. The results showed that PCA treatment (1) partly improved systemic insulin sensitivity without altering adiposity, (2) attenuated hepatic signaling pathways associated with NLRP3 inflammasome activation, including toll-like receptor 4 (TLR4)/nuclear factor kappa B (NFκB), and endoplasmic reticulum/oxidative stress, and (3) reduced circulating interleukin (IL)-1β levels. More importantly, PCA ameliorated hepatic fibrosis compared to that in the HFHS group, and the anti-fibrogenic effects of PCA were confirmed in vitro in transforming growth factor β (TGFβ) treated-LX-2 HSCs. Reference: J Nutr Biochem. 2023 Feb;112:109204. https://pubmed.ncbi.nlm.nih.gov/36400112/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	121.83
	DMF:PBS (pH 7.2) (1:6)	0.1	0.61
	DMSO	24.0	146.20
	Ethanol	21.0	127.92

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 164.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Jaganathan SK, Supriyanto E, Mandal M. Events associated with apoptotic effect of p-Coumaric acid in HCT-15 colon cancer cells. World J Gastroenterol. 2013 Nov 21;19(43):7726-34. doi: 10.3748/wjg.v19.i43.7726. PMID: 24282361; PMCID: PMC3837272. 2. Kong CS, Jeong CH, Choi JS, Kim KJ, Jeong JW. Antiangiogenic effects of p-coumaric acid in human endothelial cells. Phytother Res. 2013 Mar;27(3):317-23. doi: 10.1002/ptr.4718. Epub 2012 May 14. PMID: 22585412. 3. Moradi M, Farbood Y, Mard SA, Dianat M, Goudarzi G, Khorsandi L, Seyedian SS. p-Coumaric acid has pure anti-inflammatory characteristics against hepatopathy caused by ischemia-reperfusion in the liver and dust exposure. Iran J Basic Med Sci. 2023 Feb;26(2):164-175. doi: 10.22038/IJBMS.2022.66192.14554. PMID: 36742142; PMCID: PMC9869878. 4. Truong TMT, Seo SH, Chung S, Kang I. Attenuation of hepatic fibrosis by p-Coumaric acid via modulation of NLRP3 inflammasome activation in C57BL/6 mice. J Nutr Biochem. 2023 Feb;112:109204. doi: 10.1016/j.jnutbio.2022.109204. Epub 2022 Nov 15. PMID: 36400112.

In vitro protocol:

In vivo protocol:

1. Moradi M, Farbood Y, Mard SA, Dianat M, Goudarzi G, Khorsandi L, Seyedian SS. p-Coumaric acid has pure anti-inflammatory characteristics against hepatopathy caused by ischemia-reperfusion in the liver and dust exposure. Iran J Basic Med Sci. 2023 Feb;26(2):164-175. doi: 10.22038/IJBMS.2022.66192.14554. PMID: 36742142; PMCID: PMC9869878. 2. Truong TMT, Seo SH, Chung S, Kang I. Attenuation of hepatic fibrosis by p-Coumaric acid via modulation of NLRP3 inflammasome activation in C57BL/6 mice. J Nutr Biochem. 2023 Feb;112:109204. doi: 10.1016/j.jnutbio.2022.109204. Epub 2022 Nov 15. PMID: 36400112.

1: Ferreira JC, Reis MB, Coelho GDP, Gastaldello GH, Peti APF, Rodrigues DM, Bastos JK, Campo VL, Sorgi CA, Faccioli LH, Gardinassi LG, Tefé-Silva C, Zoccal KF. Baccharin and p-coumaric acid from green propolis mitigate inflammation by modulating the production of cytokines and eicosanoids. J Ethnopharmacol. 2021 May 29:114255. doi: 10.1016/j.jep.2021.114255. Epub ahead of print. PMID: 34062248. 2: Aquino FLT, Silva JPD, Ferro JNS, Lagente V, Barreto E. trans-Cinnamic acid, but not p-coumaric acid or methyl cinnamate, induces fibroblast migration through PKA- and p38-MAPK signalling pathways. J Tissue Viability. 2021 May 24:S0965-206X(21)00062-0. doi: 10.1016/j.jtv.2021.05.003. Epub ahead of print. PMID: 34052086. 3: Chauhan R, Azmi W, Bansal S, Goel G. Multivariate analysis of adaptive response to ferulic acid and p-coumaric acid after physiological stresses in Cronobacter sakazakii. J Appl Microbiol. 2021 May 28. doi: 10.1111/jam.15164. Epub ahead of print. PMID: 34048109. 4: Seo SH, Jo SM, Truong TTM, Zhang G, Kim DS, Lee M, Lee Y, Kang I. Peanut sprout rich in p-coumaric acid ameliorates obesity and lipopolysaccharide-induced inflammation and the inhibition of browning in adipocytes via mitochondrial activation. Food Funct. 2021 May 13. doi: 10.1039/d1fo00342a. Epub ahead of print. PMID: 33982705. 5: Ferreira PS, Victorelli FD, Rodero CF, Fortunato GC, Araújo VHS, Fonseca- Santos B, Bauab TM, Van Dijck P, Chorilli M. p-Coumaric acid loaded into liquid crystalline systems as a novel strategy to the treatment of vulvovaginal candidiasis. Int J Pharm. 2021 May 6;603:120658. doi: 10.1016/j.ijpharm.2021.120658. Epub ahead of print. PMID: 33964336. 6: Lubbers RJM, Dilokpimol A, Visser J, de Vries RP. Aspergillus niger uses the peroxisomal CoA-dependent β-oxidative genes to degrade the hydroxycinnamic acids caffeic acid, ferulic acid, and p-coumaric acid. Appl Microbiol Biotechnol. 2021 May;105(10):4199-4211. doi: 10.1007/s00253-021-11311-0. Epub 2021 May 5. PMID: 33950281; PMCID: PMC8140964. 7: Gastaldello GH, Cazeloto ACV, Ferreira JC, Rodrigues DM, Bastos JK, Campo VL, Zoccal KF, Tefé-Silva C. Green Propolis Compounds (Baccarin and p-Coumaric Acid) Show Beneficial Effects in Mice for Melanoma Induced by B16f10. Medicines (Basel). 2021 Apr 30;8(5):20. doi: 10.3390/medicines8050020. PMID: 33946188; PMCID: PMC8146786. 8: Li YH, He Q, Chen YZ, Du YF, Guo YX, Xu JY, Qin LQ. p-Coumaric acid ameliorates ionizing radiation-induced intestinal injury through modulation of oxidative stress and pyroptosis. Life Sci. 2021 Apr 26;278:119546. doi: 10.1016/j.lfs.2021.119546. Epub ahead of print. PMID: 33915129. 9: Lee S, Zhang M, Wang G, Meng W, Zhang X, Wang D, Zhou Y, Wang Z. Characterization of polyvinyl alcohol/starch composite films incorporated with p-coumaric acid modified chitosan and chitosan nanoparticles: A comparative study. Carbohydr Polym. 2021 Jun 15;262:117930. doi: 10.1016/j.carbpol.2021.117930. Epub 2021 Mar 12. PMID: 33838808. 10: Stefani T, Romo-Mancillas A, Carrizales-Castillo JJJ, Arredondo-Espinoza E, Ramírez-Estrada K, Alcantar-Rosales VM, González-Maya L, Sánchez-Carranza JN, Balderas-Renterías I, Camacho-Corona MDR. Cytotoxic Fractions from Hechtia glomerata Extracts and p-Coumaric Acid as MAPK Inhibitors. Molecules. 2021 Feb 19;26(4):1096. doi: 10.3390/molecules26041096. PMID: 33669666; PMCID: PMC7922350. 11: Xiao CL, Teng L, Li JC, Xiao XH, Yu XD. [p-Coumaric acid ameliorates depression-like behaviors induced by chronic restraint stress in mice]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2020 Sep;36(5):485-488. Chinese. doi: 10.12047/j.cjap.5970.2020.103. PMID: 33634646. 12: Nguyen LV, Nguyen KDA, Ma CT, Nguyen QT, Nguyen HTH, Yang DJ, Tran TL, Kim KW, Doan KV. p-Coumaric Acid Enhances Hypothalamic Leptin Signaling and Glucose Homeostasis in Mice via Differential Effects on AMPK Activation. Int J Mol Sci. 2021 Jan 31;22(3):1431. doi: 10.3390/ijms22031431. PMID: 33572687; PMCID: PMC7867021. 13: Souza TN, Santos FM, Alves PR, Ferro JN, Correia ACC, Melo TS, Soares WR, Andrade BS, Lagente V, Barreto E. Local administration of p-coumaric acid decreases lipopolysaccharide-induced acute lung injury in mice: In vitro and in silico studies. Eur J Pharmacol. 2021 Apr 15;897:173929. doi: 10.1016/j.ejphar.2021.173929. Epub 2021 Feb 6. PMID: 33561444. 14: Panda PK, Yang JM, Chang YH. Water-induced shape memory behavior of poly (vinyl alcohol) and p-coumaric acid-modified water-soluble chitosan blended membrane. Carbohydr Polym. 2021 Apr 1;257:117633. doi: 10.1016/j.carbpol.2021.117633. Epub 2021 Jan 12. PMID: 33541659. 15: He Y, Chen S, Tsoi B, Qi S, Gu B, Wang Z, Peng C, Shen J. Alpinia oxyphylla Miq. and Its Active Compound P-Coumaric Acid Promote Brain- Derived Neurotrophic Factor Signaling for Inducing Hippocampal Neurogenesis and Improving Post-cerebral Ischemic Spatial Cognitive Functions. Front Cell Dev Biol. 2021 Jan 18;8:577790. doi: 10.3389/fcell.2020.577790. PMID: 33537297; PMCID: PMC7849625. 16: Li L, Cai Y, Sun X, Du X, Jiang Z, Ni H, Yang Y, Chen F. Tyrosinase inhibition by p-coumaric acid ethyl ester identified from camellia pollen. Food Sci Nutr. 2020 Dec 11;9(1):389-400. doi: 10.1002/fsn3.2004. PMID: 33473301; PMCID: PMC7802545. 17: Abazari MF, Nasiri N, Karizi SZ, Nejati F, Haghi-Aminjan H, Norouzi S, Piri P, Estakhr L, Faradonbeh DR, Kohandani M, Daliri K, Sanadgol N, Askari H. An updated review of various medicinal applications of p-coumaric acid: From antioxidative and anti-inflammatory properties to effects on cell cycle and proliferation. Mini Rev Med Chem. 2021 Jan 14. doi: 10.2174/1389557521666210114163024. Epub ahead of print. PMID: 33459233. 18: Moon PD, Han NR, Lee JS, Kim HM, Jeong HJ. p-coumaric acid, an active ingredient of Panax ginseng, ameliolates atopic dermatitis-like skin lesions through inhibition of thymic stromal lymphopoietin in mice. J Ginseng Res. 2021 Jan;45(1):176-182. doi: 10.1016/j.jgr.2020.06.004. Epub 2020 Jul 5. PMID: 33437169; PMCID: PMC7790890. 19: Kim H, Choi Y, An Y, Jung YR, Lee JY, Lee HJ, Jeong J, Kim Z, Kim K. Development of p-Coumaric Acid Analysis in Human Plasma and Its Clinical Application to PK/PD Study. J Clin Med. 2020 Dec 30;10(1):108. doi: 10.3390/jcm10010108. PMID: 33396842; PMCID: PMC7795779. 20: Jiang T, Li C, Yan Y. Optimization of a p-Coumaric Acid Biosensor System for Versatile Dynamic Performance. ACS Synth Biol. 2021 Jan 15;10(1):132-144. doi: 10.1021/acssynbio.0c00500. Epub 2020 Dec 30. PMID: 33378169; PMCID: PMC8130012.