| Identification | More | [Name]
3-(3,4-DIHYDROXYPHENYL)PROPIONIC ACID | [CAS]
1078-61-1 | [Synonyms]
3-(3,4-DIHYDROXYPHENYL)PROPIONIC ACID
3,4-DIHYDROCAFFEIC ACID
3,4-DIHYDROXYHYDROCINNAMIC ACID
BETA-(3,4-DIHYDROXYPHENYL) PROPIONIC ACID
DIHYDROCAFFEIC ACID
HYDROCAFFEIC ACID
3,4-dihydroxy-benzenepropanoicaci
3,4-dihydroxybenzenepropanoicacid
3,4-dihydroxy-hydrocinnamicaci
3,4-Dihydroxyhydrocinnamic acid~Hydrocaffeic acid
3,4-dihydroxyphenylpropionic acid
3-(3,4-Dihydroxyphenyl)propionic acid, 98+%
DIHYDROCAFFEIC ACID(RG)
3-(3,4-Dihydroxyphenyl)propionic acid, Hydrocaffeic acid
3-(3,4-Dihydroxyphenyl)propanoic acid | [EINECS(EC#)]
214-083-8 | [Molecular Formula]
C9H10O4 | [MDL Number]
MFCD00002776 | [Molecular Weight]
182.17 | [MOL File]
1078-61-1.mol |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
4.75±0.10(Predicted) | [color ]
Pale Beige to Pale Brown | [Water Solubility ]
Slightly soluble in water. | [BRN ]
2213449 | [InChI]
InChI=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) | [InChIKey]
DZAUWHJDUNRCTF-UHFFFAOYSA-N | [SMILES]
C1(CCC(O)=O)=CC=C(O)C(O)=C1 | [LogP]
0.115 (est) | [CAS DataBase Reference]
1078-61-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
MW5143500
|
| Hazard Information | Back Directory | [Description]
Dihydrocaffeic acid is a polyphenol that has diverse biological activities, including antioxidant, neuroprotective, and enzyme inhibitory properties.1,2 Dihydrocaffeic acid scavenges ABTS (Item No. 27317; IC50 = 81.86 μg/ml) and 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805; 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; Item No. 82250) in a concentration-dependent manner.1 It also decreases endothelial nitric oxide synthase (eNOS) activity in EA.hy926 human endothelial cells in a concentration-dependent manner.3 In vivo, dihydrocaffeic acid (30 mg/kg) decreases infarct size in a rat model of transient ischemia induced by middle cerebral artery occlusion (MCAO).2 | [Chemical Properties]
Brown Solid | [Uses]
Dihydrocaffeic 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. | [Definition]
ChEBI: 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 50]
Microbial Metabolite; p38 MAPK; Human Endogenous Metabolite | [storage]
Store at -20°C | [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 |
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