1108192-01-3

Basic information

• Product Name: (4S)-5-(3,4-dihydroxyphenyl)-γ-valerolactone
• Synonyms: (4S)-5-(3,4-dihydroxyphenyl)-γ-valerolactone
• CAS NO: 1108192-01-3
• Molecular Weight: 208.214
• Mol File: 1108192-01-3.mol

Chemical Properties

• CAS DataBase Reference: (4S)-5-(3,4-dihydroxyphenyl)-γ-valerolactone(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-5-(3,4-dihydroxyphenyl)-γ-valerolactone(1108192-01-3)
• EPA Substance Registry System: (4S)-5-(3,4-dihydroxyphenyl)-γ-valerolactone(1108192-01-3)

Safety Data

• Hazardous Substances Data: 1108192-01-3(Hazardous Substances Data)

Upstream product

• 1108192-16-0 C₂₇H₅₀O₆Si₂ 
• 1108192-18-2 C₂₇H₄₈O₆Si₂ 
• 6379-72-2 1,2-dimethoxy-4-(E)-propenylbenzene 
• 2859-78-1 4-Bromoveratrole 
• 137688-21-2 (-)-(S)-2-(but-3-enyl)oxirane 

Relevant articles and documents

Concise synthesis of catechin metabolites 5-(30,40-dihydroxyphenyl)-γ-valerolactones (dhpv) in optically pure form and their stereochemical effects on skin wrinkle-reducing activities

A concise and scalable synthetic route for optically pure (4S) and (4R)-5-(30,40-dihydroxyphenyl)-γ-valerolactones (DHPVs), catechin metabolites, has been developed via the efficient construction of a γ-valerolactone moiety from hexe

Efficient and divergent enantioselective syntheses of DHPVs and anti-inflammatory effect on IEC-6 cells

Despite numerous reports on the beneficial effects of catechin or epicatechin contained in tea and cacao extract on human health, a conclusive and precise molecular mechanism has not been elucidated. Metabolism of chemical compounds in gut microbiota recently gained significant attention, and extensive studies have been devoted in this field. In conjunction with these results, our group focused on the anti-inflammatory effects of both enantiomers of DHPV (5-(3',4'-dihydroxyphenyl)-γ-valerolactone), produced in the intestine by microbiota metabolism, on IEC-6 cells. Divergent and efficient enantioselective synthesis of (S)- and (R)-DHPV was efficiently achieved by cross-metathesis and Sharpless asymmetric dihydroxylation as a key reaction for four steps in 16% and 14% overall yields, respectively. The anti-inflammatory effects of two enantiomers were tested on IEC-6 cells, and we found that (S)-DHPV was more active than (R)-DHPV. This result implicates that the metabolite produced in the gut has beneficial effects on IEC-6 cells of rat intestines, and the chirality of the metabolite is important for its anti-inflammatory activity. This also provided information for the future discovery of novel small molecular therapeutics for the treatment of inflammatory bowel disease.

Synthesis of γ-valerolactones as the tea catechin metabolites

The synthesis of optically active γ-valerolactones in order to characterize the absolute configuration of the one of the (-)-epicatechin gallate metabolites was described. The determination of stereochemistry at C(4) position of γ-valerolactone suggested