26539-01-5

Basic information

• Product Name: 3-(3,5-DIHYDROXYPHENYL)-1-PROPANOICACID
• Synonyms: 3-(3,5-DIHYDROXYPHENYL)-1-PROPANOICACID;3,5-dihydroxyphenylpropionic acid;3,5-Dihydroxyhydrocinnamic acid
• CAS NO: 26539-01-5
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.17
• Mol File: 26539-01-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 415.5 °C at 760 mmHg
• Flash Point: 219.2 °C
• Appearance: /
• Density: 1.398 g/cm³
• Vapor Pressure: 1.2E-07mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.68±0.10(Predicted)
• BRN: 2723516
• CAS DataBase Reference: 3-(3,5-DIHYDROXYPHENYL)-1-PROPANOICACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3,5-DIHYDROXYPHENYL)-1-PROPANOICACID(26539-01-5)
• EPA Substance Registry System: 3-(3,5-DIHYDROXYPHENYL)-1-PROPANOICACID(26539-01-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 26539-01-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H10O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h3-5,10-11H,1-2H2,(H,12,13)

Synthetic route

2-(3',5'-Dimethoxyphenyl)-ethane-1,1-dicarboxylic acid (730-01-8) → 3-(3′,5′-dihydroxyphenyl)propionic acid (26539-01-5)

Conditions	Yield
With pyridine hydrochloride at 220℃; for 1h; Yield given;

epigallocatechin (970-73-0, 1617-55-6, 3371-27-5, 13425-13-3, 136892-45-0, 970-74-1) → 4-hydroxy-5-(3,5-dihydroxyphenyl)valeric acid (1204316-08-4) + 3-(3′,5′-dihydroxyphenyl)propionic acid (26539-01-5) + (-)-5-(3',5'-dihydroxyphenyl)-(4R)-γ-valerolactone

Conditions	Yield
With Wistar rat intestinal flora In methanol; water for 96h; Microbiological reaction; Phosphate buffer; Anaerobic conditions;	A n/a B 3 mg C n/a

(+)-trans-verbenol (22339-08-8) + 3-(3′,5′-dihydroxyphenyl)propionic acid (26539-01-5) → 3-((R)-1-Hydroxy-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-3-yl)-propionic acid (71555-80-1)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane for 3h; Ambient temperature;

Upstream product

• 730-01-8 2-(3',5'-Dimethoxyphenyl)-ethane-1,1-dicarboxylic acid 
• 970-73-0 epigallocatechin 

Relevant articles and documents

Metabolism of (-)-epigallocatechin gallate by rat intestinal flora

Anaerobic metabolism of ( - )-epigallocatechin gallate (EGCg) by rat intestinal bacteria was investigated in vitro. First, intestinal bacteria which are capable of hydrolyzing EGCg to ( - )epigallocatechin (EGC) and gallic acid (2) were screened with 169 strains of enteric bacteria. As a result, Enterobacter aerogenes, Raoultella planticola, Klebsiella pneumoniae susp. pneumoniae, and Bifidobacterium longum subsp. infantis were found to hydrolyze EGCg. Subsequent steps of EGCg metabolism are degradation of EGC (1) by intestinal bacteria. Then, EGC was incubated with rat intestinal bacteria in 0.1 M phosphate buffer (pH 7.1) and the degradation products were analyzed with time by HPLC or LC-MS. Further, the products formed from EGC were isolated and identified by LC-MS and NMR analyses. The results revealed that EGC was converted first to 1-(3', 4', 5'-trihydroxyphenyl)-3-(2 , 4 , 6 -trihydroxyphenyl)propan-2-ol (3) by reductive cleavage between 1 and 2 positions of EGC, and subsequently metabolite 3 was converted to 1-(3', 5'-dihydroxyphenyl)-3-(2 , 4 , 6 -trihydroxyphenyl)propan-2-ol (4) followed by the conversion to 5-(3, 5-dihydroxyphenyl)-4-hydroxyvaleric acid (5) by decomposition of the phloroglucinol ring in metabolite 4. This degradation pathway was considered to be the major route of EGCg metabolism in the in vitro study, but two minor routes were also found. In addition to the in vitro experiments, metabolites 3, 4, 5, and 6 were detected as the metabolites after direct injection of EGC into rat cecum. When EGCg was administered orally to the rats, metabolites 4, 5, 6, 11, and 12 were found in the feces. Among the metabolites detected, metabolite 5 was dominant both in the cecal contents and feces. These findings suggested that the metabolic pathway of EGCg found in the in vitro study may be regarded as reflecting its metabolism in vivo.