3-(3,4-Dihydroxyphenyl)propionic acid

Base Information

• Chemical Name: 3-(3,4-Dihydroxyphenyl)propionic acid
• CAS No.: 1078-61-1
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• European Community (EC) Number: 214-083-8
• NSC Number: 624007,407275
• UNII: MSW0228VUB
• DSSTox Substance ID: DTXSID40221919
• Nikkaji Number: J12.480J
• Wikipedia: Dihydrocaffeic_acid
• Wikidata: Q10395580
• Metabolomics Workbench ID: 37242
• ChEMBL ID: CHEMBL136927
• Mol file: 1078-61-1.mol

Synonyms:3,4-dihydroxyhydrocinnamic acid;3,4-dihydroxyphenylpropionic acid;3,4-dihydroxyphenylpropionic acid, potassium salt;3-(3,4-dihydroxyphenyl)propionic acid;dihydrocaffeic acid

Chemical Property of 3-(3,4-Dihydroxyphenyl)propionic acid

Chemical Property:

• Vapor Pressure: 1.02E-07mmHg at 25°C
• Melting Point: 136-139 ºC(lit.)
• Boiling Point: 417.5 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 220.4 °C
• PSA: 77.76000
• Density: 1.398 g/cm³
• LogP: 1.11500
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water.
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

Dihydrocaffeic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CCC(=O)O)O)O
• 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).
• 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. 3-(3,4-Dihydroxyphenyl)propionic acid it can be used to produce 3-(3,4-dihydroxy-phenyl)-propionic acid octyl ester by heating.

Technology Process of 3-(3,4-Dihydroxyphenyl)propionic acid

There total 28 articles about 3-(3,4-Dihydroxyphenyl)propionic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

caffeic acid (331-39-5,501-16-6) → dihydrocaffeic acid (1078-61-1)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; under 760.051 Torr; Inert atmosphere;

DOI:10.1021/jm400374q

Reference yield: 98.0%

4-hydroxyphenylpropionic acid (501-97-3) → dihydrocaffeic acid (1078-61-1)

Guidance literature:

With Agaricus bisporus; oxygen; In aq. phosphate buffer; dichloromethane; at 25 ℃; for 24h; pH=7; Reagent/catalyst;

DOI:10.1016/j.bmc.2013.10.026

Reference yield: 85.0%

3-(4-hydroxy-3-methoxyphenyl)propionic acid (1135-23-5) → dihydrocaffeic acid (1078-61-1)

Guidance literature:

With hydrogenchloride; In water; at 250 ℃; for 6h; under 37503.8 Torr; Time; Autoclave; Inert atmosphere; Green chemistry;

DOI:10.1039/d0gc04268d

upstream raw materials:

caffeic acid

3-(4-hydroxy-3-methoxyphenyl)propionic acid

caffeic acid

3,4-methoxycinnamic acid

Downstream raw materials:

3-(3,4-dihydroxyphenyl)propanoic acid propyl ester

3,4-methoxycinnamic acid

(3,4-dioctyloxyphenyl)3'-propionic acid

3-[3,4-bis(dodecyl-1-oxy)phenyl]propionic acid

Refernces

• 1、 Omura,Matsuura. "-". . p. 3475. Retrieved 1968.
• 2、 Takahashi,Miyazawa, Mitsuo. "Tyrosinase inhibitory activities of cinnamic acid analogues". . p. 913 - 918. Retrieved 2010.
• 3、 Matsuura,Omura. "-". . p. 127. Retrieved 1966.
• 4、 Ponnapalli, M. Gowri,Annam, S. Ch. V. A. Rao,Ravirala, Saidulu,Sukki, Sushma,Ankireddy, Madhu,Tuniki, V. Raju. "Unusual isomeric corniculatolides from mangrove, Aegiceras corniculatum". . p. 275 - 279. Retrieved 2012.
• 5、 Bomon, Jeroen,Bal, Mathias,Achar, Tapas Kumar,Sergeyev, Sergey,Wu, Xian,Wambacq, Ben,Lemière, Filip,Sels, Bert F.,Maes, Bert U. W.. "Efficient demethylation of aromatic methyl ethers with HCl in water". supporting information. p. 1995 - 2009. Retrieved 2021/03/26.
• 6、 -. "METHOD FOR ENHANCING DELIVERY OF THERAPEUTIC DRUGS TO TREATMENT SITES". Paragraph 0135-0137. . Retrieved 2019/05/18.