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Dihydrocaffeic acid

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CAS:1078-61-1
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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
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
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.
in vivo

Dihydrocaffeic acid (3-30 mg/kg, i.p.) protects against ischemia-induced neuronal damage and cerebral edema in a rat model of focal cerebral ischemia[8].

IC 50Microbial Metabolite; p38 MAPK; Human Endogenous Metabolite
References[1] HOLIM JANG. Effects of phenolic acid metabolites formed after chlorogenic acid consumption on retinal degeneration in vivo[J]. Molecular Nutrition & Food Research, 2015, 59 10: 1918-1929. DOI: 10.1002/mnfr.201400897
[2] KYUNGJIN LEE  Youngmin B  Beom Joon Lee. Protective Effects of Dihydrocaffeic Acid, a Coffee Component Metabolite, on a Focal Cerebral Ischemia Rat Model.[J]. Molecules, 2015, 20 7: 11930-11940. DOI: 10.3390/molecules200711930
[3] JUNJUN HUANG  James M M  Tomas de Paulis. Antioxidant effects of dihydrocaffeic acid in human EA.hy926 endothelial cells[J]. Journal of Nutritional Biochemistry, 2004, 15 12: Pages 722-729. DOI: 10.1016/j.jnutbio.2004.07.002
Tag:Dihydrocaffeic acid(1078-61-1) Related Product Information
Methyldopa DL-DOPA 3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID 3-(3,4-METHYLENEDIOXYPHENYL)PROPIONIC ACID 3-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACID CINOXACIN Oxolinic acid (2S)-2-Amino-3-(3,4-dimethoxyphenyl)-2-methyl-propanoic acid 3,4-Dimethoxyhydrocinnamic acid Dihydrocaffeic acid Levodopa (2RS,3RS)-2-AMINO-3-(3,4-DIHYDROXY-PHENYL)-3-HYDROXY-PROPIONIC ACID BETANIN ETHYL 3-(3,4,5-TRIMETHOXYPHENYL)PROPIONATE (R)-2-Amino-3-(3,4-dihydroxyphenyl)propionic acid DROXIDOPA DL-α-Hydrazino-α-methyl-β-(3,4-dihydroxyphenyl)propionic acid (R)-2-Hydroxy-3-(3,4-dihydroxyphenyl)propionic acid