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p-Hydroxy-cinnamic acid

p-Hydroxycinnamic acid

CAS: 501-98-4;7400-08-0

Molecular Formula: C9H8O3

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p-Hydroxy-cinnamic acid - Names and Identifiers

Name p-Hydroxycinnamic acid
Synonyms AKOS 221-47
AKOS BAR-2479
p-Coumaric acid
trans-Coumaricacid
TRANS-P-CUMARIC ACID
trans-p-Coumaric acid
TRANS-P-COUMARIC ACID
TRANS-4-COUMARIC ACID
p-Hydroxycinnamic acid
4-hydroxycinnamic acid
p-Hydroxy-cinnamic acid
trans-p-hydroxycinnamicacid
trans-4-Hydroxycinnamic acid
TRANS-4-HYDROXYCINNAMIC ACID
trans-p-Hydroxycinnamic acid
3-(4-Hydroxyphenyl)acrylic acid
trans-P-coumaric acid crystalline
trans-4-Hydroxyphenylpropenoic Acid
3-(4-Hydroxyphenyl)-2-propenoic acid
2-(4-hydroxyphenyl)prop-2-enoic acid
3-(4-hydroxyphenyl)prop-2-enoic acid
(2E)-3-(4-hydroxyphenyl)prop-2-enoate
(e)-3-(4-hydroxyphenyl)-2-propenoicacid
(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
CAS 501-98-4
7400-08-0
EINECS 610-511-6
InChI InChI=1/C9H8O3/c1-6(9(11)12)7-2-4-8(10)5-3-7/h2-5,10H,1H2,(H,11,12)
InChIKey NGSWKAQJJWESNS-ZZXKWVIFSA-N

p-Hydroxy-cinnamic acid - Physico-chemical Properties

Molecular FormulaC9H8O3
Molar Mass164.16
Density1.1403 (rough estimate)
Melting Point214°C (dec.)(lit.)
Boling Point231.61°C (rough estimate)
Flash Point167.2°C
Water Solubilitysoluble
Solubility Soluble in methanol, ethanol, DMSO and other organic solvents
Vapor Presure7.19E-05mmHg at 25°C
AppearancePale yellow to beige crystalline powder
ColorOff-white to beige or greenish
Merck14,2560
BRN2207383
pKa4.65±0.10(Predicted)
Storage ConditionKeep in dark place,Sealed in dry,Room Temperature
Refractive Index1.4500 (estimate)
MDLMFCD00004399
Physical and Chemical Properties

light yellow crystals
melting range ℃ 210-213

UseFor pharmaceutical and perfumery industrial intermediates

p-Hydroxy-cinnamic acid - Risk and Safety

Hazard SymbolsXi - Irritant
Irritant
Risk Codes36/37/38 - Irritating to eyes, respiratory system and skin.
Safety DescriptionS26 - 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 Germany2
RTECSGD9095000
HS Code29163990

p-Hydroxy-cinnamic acid - Reference

Reference
Show more
1. Yin Haili, Zhao Yiyu, Guo Hongzhu, Chen Yougen, Fu Xintong. Quantitative analysis of six organic acids in ginkgo biloba leaves [J]. Chinese Journal of new drugs, 2019,28(12):1505-1510.
2. Jia Rui, Liu Yuqiang, Qi Xiaoxu, etc. Pharmacokinetics of total flavonoids from Ampelopsis grossedentata in rats [J]. Asia-Pacific traditional medicine, 2017, 13(005):8-10.
3. Zhao Yiyu, Guo Hongzhu, Chen Yougen, etc. Study on difference of flavonol glycosides, terpene lactones, phenols and carboxylic acids in ginkgo biloba extract based on UPLC-QTOF-MSE metabolomics [J]. Chinese Journal of Pharmacy, 2017, 026(011):789-804.
4. Wang Hongmei, Peng Lu, Wang Yue, etc. Comparison of physicochemical properties and phenolic composition of five grape varieties [J]. Food and Fermentation Industry, 2019, 45(07):78-85.
5. Lu chaogeng, Yang Jianjian, et al. Determination of nine organic acids in dendrobium officinale by UPLC-MS/MS [J]. Chinese herbal medicine 2017 040(006):1360-1363.
6. [IF = 4.411] Ying Zhang et al."Composition Identification in men Cuscutae by Ultra-High-Performance Liquid Chromatography (UPLCs) Coupled to Electrospray Ionization Mass Spectrometry."Molecules. 2018 May;23(5):1199
7. [IF=4.694] Jia Liu et al."Exploring the Antioxidant Effects and Periodic Regulation of Cancer Cells by Polyphenols Produced by the Fermentation of Grape Skin by Lactobacillus plantarum KFY02."Biomolecules. 2019 Oct;9(10):575
8. [IF=4.35] Wanpei Tang et al."Phenolic Compounds Profile and Antioxidant Capacity of Pitahaya Fruit Peel from Two Red-Skinned Species (Hylocereus polyrhizus and Hylocereus undatus)."Foods. 2021 Jun;10(6):1183
9. [IF=3.935] Yong-Sheng Wu et al."Chemical profiling of Callicarpa nudiflora and its effective compounds identification by compound-target network analysis."J Pharmaceut Biomed. 2020 Apr;182:113110
10. [IF=3.645] Zhihui Li et al."Identification of components and metabolites in plasma of type 2 diabetic rat after oral administration of Jiao-Tai-Wan using ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry."J Sep Sci. 2020 Jul;43(13):
11. [IF=3.411] Shi Guiqin et al."UPLC-ESI-MS/MS Analysis and Evaluation of Antioxidant Activity of Total Flavonoid Extract from Paeonia lactiflora Seed Peel and Optimization by Response Surface Methodology (RSM)."Biomed Res Int. 2021;2021:7304107
12. [IF=3.119] Jia Liu et al."Grape skin fermentation by Lactobacillus fermentum CQPC04 has anti-oxidative effects on human embryonic kidney cells and apoptosis-promoting effects on human hepatoma cells."Rsc Adv. 2020 Jan;10(8):4607-4620
13. [IF=1.813] Zhang Ying et al."Comparative Studies on Chemical Contents and Effect in Kidney-Yang Deficiency Rats of Salt-Processed Product and Wine-Processed Product of Cuscutae Semen."Evid-Based Compl Alt. 2019;2019:2049497
14. [IF=5.64] Jin-Wei Zhou et al."Quorum Sensing Inhibition and Metabolic Intervention of 4-Hydroxycinnamic Acid Against Agrobacterium tumefaciens.."Front Microbiol. 2022 Mar;13:830632-830632
15. [IF=3.645] Lewen Xiong et al."Study on phenolic acids of Lonicerae japonicae Flos based on ultrahigh performance liquid chromatography-tandem mass spectrometry combined with multivariate statistical analysis."JOURNAL OF SEPARATION SCIENCE

p-Hydroxy-cinnamic acid - Reference Information

NIST chemical information Information provided by: webbook.nist.gov (external link)
EPA chemical information Information provided by: ofmpub.epa.gov (external link)
introduction trans-4-hydroxycinnamic acid is a cinnamic acid compound, which is widely distributed in many natural products such as propolis, vegetables and fruits and is a natural antioxidant. Mainly in the form of organic acid esters, polyglycosides and amides widely exist in nature.
traits 4-hydroxycinnamic acid is white or light yellow powder. Soluble in hot ether, hot ethanol, slightly soluble in benzene, insoluble in petroleum ether.
Uses 4-hydroxycinnamic acid is an intermediate of the expectorant rhododendron, and can also be used to synthesize the anti-epinephrine drug esmolol.
4-Hydroxycoumarin is an anticoagulant rodenticide, rodenticide, bromadiolone, bromadiolone, bromadiolone, bromadiolone, bromadiolone, bromaolone, thiamol, kesuoling, etc. The intermediates can also be used to make anti-blood clotting drugs such as dicoumarin ethyl ester and ketonobenzyl coumarin.
Used as an intermediate in medicine and perfume industry
perfume synthesis. An intermediate of the expectorant rhododendron. Trans-4-hydroxycinnamic acid is the e-isomer of p-coumaric acid, a hydroxyl derivative of cinnamic acid, which has antioxidant properties. Coumaric acid is a major component of lignocellulose. Studies have shown that p-coumaric acid can reduce the risk of cancer by reducing the formation of carcinogenic nitrosamines.
production method its preparation method is to use acetylsalicylchloride as raw material, react with diethyl malonate in acetonitrile solvent in the presence of magnesium chloride, then add triethylamine, react at 0 ℃ for 1h, obtain (2-acetoxylbenzoyl) diethyl malonate product, then heat to 50 ℃ in potassium hydroxide/methanol solution for 3h, the product is obtained by cyclization. It is also possible to use ethyl acetoacetate as raw material, in the presence of sodium hydroxide, in the solvent of isobutyl methyl ketone and acetylsalicylchloride at 15~20 ℃ for 3.5 h to obtain 2-(2-hydroxybenzoyl) acetyl sodium acetate salt, the reaction product and hydrochloric acid at 25~30 ℃ for 30min to obtain 3-acetyl-4-hydroxycoumarin, and then under concentrated sulfuric acid, the product is obtained by heating at 90~95 ℃ for 4 hours. It is also possible to use 2-hydroxyacetophenone as raw material, in the presence of potassium carbonate, to pass 5.88MPa carbon dioxide in an autoclave, to pass at room temperature for 15h, and then to maintain at 60 ℃ for 15h, to form 2-hydroxyphenyl-3-oxypropionic acid, and then to synthesize the product.
Last Update：2024-04-09 19:05:12
p-Hydroxy-cinnamic acid
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p-Hydroxy-cinnamic acid
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