138760-70-0

Basic information

• Product Name: 2(5H)-Furanone, 3,4-dihydroxy-5-(hydroxymethyl)-, (R)- (9CI)
• Synonyms: 2(5H)-Furanone, 3,4-dihydroxy-5-(hydroxymethyl)-, (R)- (9CI)
• CAS NO: 138760-70-0
• Molecular Formula: C5H6O5
• Molecular Weight: 146.09814
• Product Categories: ALDEHYDE
• Mol File: 138760-70-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(5H)-Furanone, 3,4-dihydroxy-5-(hydroxymethyl)-, (R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(5H)-Furanone, 3,4-dihydroxy-5-(hydroxymethyl)-, (R)- (9CI)(138760-70-0)
• EPA Substance Registry System: 2(5H)-Furanone, 3,4-dihydroxy-5-(hydroxymethyl)-, (R)- (9CI)(138760-70-0)

Safety Data

• Hazardous Substances Data: 138760-70-0(Hazardous Substances Data)

Usage

Chemical structure

A derivative of furanone with two hydroxyl groups (-OH) at the 3 and 4 positions, and a hydroxymethyl group (-CH2OH) at the 5 position.

Natural sources

Found in various natural sources.

Antioxidant properties

Has the potential to scavenge free radicals and protect against oxidative stress.

Anti-inflammatory properties

May have potential anti-inflammatory properties.

Therapeutic applications

Research has shown that 2(5H)-Furanone, 3,4-dihydroxy-5-(hydroxymethyl)-, (R)- (9CI) may have potential therapeutic applications in the treatment of various diseases and disorders.

Use in pharmaceutical and cosmetic products

Considered a promising candidate for use in pharmaceutical and cosmetic products.

Upstream product

• 5336-08-3 D-Ribono-1,4-lactone 
• 174339-86-7 D-erythro-ascorbic acid 5-(β-D-glucoside) 
• 138760-69-7 3,4-O-Benzylidene-D-erythro-pentulosono-1,5-lactone hydrate 
• 52298-32-5 benzyl O^α-benzoylglycolate 

Relevant articles and documents

Production, stability, and antioxidative and antimicrobial activities of two l-ascorbate analogues from phycomyces blakesleeanus: D-erythroascorbate and d-erythroascorbate glucoside

D-Erythroascorbate (D-EAA), a five-carbon analogue of L-ascorbate (L-AA), and D-erythroascorbate monoglucoside (D-EAAG) are accumulated in Phycomyces blakesleeanus grown on glucose (99.5 and 1084 μg/g mycelial dry weight, respectively) and also excreted into the culture medium. Both compounds showed UV spectral properties and ionization constants similar to those of L-AA. D-EAAG was much more stable to aerobic oxidation than D-EAA and L-AA at acidic pH. D-EAAG is synthesized from D-erythroascorbate by a mycelial glucosyltransferase activity that uses UDP-glucose as glucose substrate donor with Km = 2.5 mM and 41.3 μM for D-EAA. This glucosyltransferase activity was maximal in the stationary growth phase in parallel with maximal production of D-EAAG. The presence of D-arabinose or D-arabinono-1,4-lactone in the culture medium produces the maximal accumulation of D-EAA and D-EAAG (about 30- and 4-fold with respect to that obtained in glucose culture). Both compounds showed greater antioxidant activity than L-AA and other standard antioxidants, with a capacity similar to that of L-AA to inhibit the growth of Escherichia coli.

Synthesis of D-erythroascorbic acid from D-glucose

Reaction of a 4:1 mixture of D-ribono- and D-arabinono-1,4-lactones with benzaldehyde and hydrochloric acid gave 59percent crystalline 3,4-O-benzylidene-D-ribono-1,5-lactone.This acetal was oxidized with manganese dioxide in acetone to its 2-keto-derivative (6) in 76percent yield.Acid-catalyzed methanolysis of 6 gave a syrupy mixture of products, which upon tautomerization in hot methanolic sodium acetate followed by removal of sodium ions gave 78percent D-erythroascorbic acid (7).The overall yield of 7 starting from D-glucose was 20percent.