Dihydrocaffeic acid

Dihydrocaffeic acid Basic information
Product Name:Dihydrocaffeic acid
Synonyms:3-(3,4-dihydroxyphenyl)propanoate;3-(3,4-Dihydroxyphenyl)propionic acid, Hydrocaffeic acid;3-(3,4-Dihydroxyphenyl)propionic acid, 98+%;DIHYDROCAFFEIC ACID(RG);3-(3,4-DIHYDROXYPHENYL)PROPIONIC ACID;3,4-DIHYDROXYHYDROCINNAMIC ACID;3,4-DIHYDROCAFFEIC ACID;BETA-(3,4-DIHYDROXYPHENYL) PROPIONIC ACID
CAS:1078-61-1
MF:C9H10O4
MW:182.17
EINECS:214-083-8
Product Categories:Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Aromatic Cinnamic Acids, Esters and Derivatives
Mol File:1078-61-1.mol
Dihydrocaffeic acid Structure
Dihydrocaffeic acid Chemical Properties
Melting point 136-139 °C(lit.)
Boiling point 418℃
density 1.398
Fp 220℃
storage temp. Inert atmosphere,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
pka4.75±0.10(Predicted)
form Solid
color Pale Beige to Pale Brown
Water Solubility Slightly soluble in water.
BRN 2213449
InChIInChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
InChIKeyDZAUWHJDUNRCTF-UHFFFAOYSA-N
SMILESC1(CCC(O)=O)=CC=C(O)C(O)=C1
LogP0.115 (est)
CAS DataBase Reference1078-61-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS MW5143500
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Dihydrocaffeic acid Usage And Synthesis
DescriptionDihydrocaffeic acid is a polyphenol that has diverse biological activities, including antioxidant, neuroprotective, and enzyme inhibitory properties. Dihydrocaffeic acid scavenges ABTS (; IC50 = 81.86 μg/ml) and 2,2-diphenyl-1-picrylhydrazyl (DPPH; ; IC50 = 192.86 μg/ml) radicals and increases the survival of RGC-5 mouse retinal ganglion cells under hypoxic conditions and in the presence of S-nitroso-N-acetyl-D,L-penicillamine (SNAP; ) in a concentration-dependent manner. It also decreases endothelial nitric oxide synthase (eNOS) activity in EA.hy926 human endothelial cells in a concentration-dependent manner. In vivo, dihydrocaffeic acid (30 mg/kg) decreases infarct size in a rat model of transient ischemia induced by middle cerebral artery occlusion (MCAO).
Chemical PropertiesBrown Solid
UsesDihydrocaffeic Acid is a natural product containing a catechol group with an α,β-unsaturated carboxylic acid chain. Dihydrocaffeic Acid has been shown to have hepatoprotective activity. Dihydrocaffei c Acid is a metabolite of Caffeic Acid (C08000) with potent antioxidant properties.
Uses3-(3,4-Dihydroxyphenyl)propionic acid it can be used to produce 3-(3,4-dihydroxy-phenyl)-propionic acid octyl ester by heating.
DefinitionChEBI: A monocarboxylic acid that is 3-phenylpropionic acid substituted by hydroxy groups at positions 3 and 4. It is a metabolite of caffeic acid and exhibits antioxidant activity.
3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID DL-DOPA B-(3,4-DIHYDROXYPHENYL)PROPIONIC ACID ETHYL ESTER CINOXACIN 3,4-Dimethoxyhydrocinnamic acid L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE diethyl (3,4,5-trimethoxybenzoyl)malonate Methyldopa (2S)-2-Amino-3-(3,4-dimethoxyphenyl)-2-methyl-propanoic acid (S)-2-AMINO-3-(3,4-DIMETHOXY-PHENYL)-PROPIONIC ACID 2,4,5-TRIHYDROXY-DL-PHENYLALANINE HYDROXINAPINIC ACID METHYL 3-(3,4,5-TRIMETHOXYPHENYL)PROPANOATE 3-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACID Ethyl 3,4,5-trimethoxybenzoylacetate 2-(3,4-DIMETHOXYPHENYL)-1-METHYL-5-OXO-3-PYRROLIDINECARBOXYLIC ACID 3-(3,4-METHYLENEDIOXYPHENYL)PROPIONIC ACID 2-(1,3-BENZODIOXOL-5-YL)-1-METHYL-5-OXO-3-PYRROLIDINECARBOXYLIC ACID

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