Dihydrocaffeic acid Chemical Properties

Melting point:

136-139 °C(lit.)

Boiling point:

418℃

Density 

1.398

Flash point:

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

MW5143500

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Dihydrocaffeic acid Usage And Synthesis

Description

Dihydrocaffeic 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 Properties

Brown Solid

Uses

3-(3,4-Dihydroxyphenyl)propionic acid it can be used to produce 3-(3,4-dihydroxy-phenyl)-propionic acid octyl ester by heating.

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

IC 50

Microbial 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

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