26094-91-7

Basic information

• Product Name: L-Erythroascorbic acid
• Synonyms: Araboascorbic acid, L-;L-Araboascorbic acid;L-Erythorbic acid;L-Erythroascorbic acid;L-erythro-Ascorbic acid;L-erythro-Hex-2-enonic acid, γ-lactone (8CI, 9CI);(4S,5S)-2,3,4,5,6-Pentahydroxy-2-hexenoic acid 1,4-lactone;L-Isoascorbic acid
• CAS NO: 26094-91-7
• Molecular Formula: C₆H₈O₆
• Molecular Weight: 176.12
• Mol File: 26094-91-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Erythroascorbic acid(CAS DataBase Reference)
• NIST Chemistry Reference: L-Erythroascorbic acid(26094-91-7)
• EPA Substance Registry System: L-Erythroascorbic acid(26094-91-7)

Safety Data

• Hazardous Substances Data: 26094-91-7(Hazardous Substances Data)

Upstream product

• 49653-17-0 ethyl 2-ethoxyglycolate 
• 299-36-5 ascorbate 
• 50-81-7 ascorbic acid 
• 63983-50-6 ascorbate 
• 185675-51-8 (R)-3,4-Bis-benzyloxy-5-((2S,4S)-2-phenyl-[1,3]dioxolan-4-yl)-5H-furan-2-one 
• 185675-50-7 (R)-3,4-Bis-benzyloxy-5-((2R,4S)-2-phenyl-[1,3]dioxolan-4-yl)-5H-furan-2-one 
• 185675-52-9 (S)-3,4-Bis-benzyloxy-5-((2R,4S)-2-phenyl-[1,3]dioxolan-4-yl)-5H-furan-2-one 
• 36136-58-0 L-erythro-3,4,5-Trihydroxy-2-oxo-valeraldehyd 
• 99663-32-8 (2R)-3,4-dibenzyloxy-2-[(1S)-1,2-dihydroxyethyl]-2H-furan-5-one 

Downstream Products

• 7723-73-1 5-(1,2-dihydroxy-ethyl)-furan-2,3,4-trione 
• 88-67-5 2-Iodobenzoic acid 
• 490-83-5 L-threo-2,3-hexodiulosono-1,4-lactone 
• 6614-52-4 5,6-O-cycloheyxlidene-(L)-ascorbic acid 
• 15042-01-0 O-5,6-isopropylidene-L-(+)ascorbic acid 
• 1128-23-0 L-gulono-1,4-lactone 
• 15667-21-7 D-erythronolactone 
• 1129294-89-8 5-(1,2-Dihydroxy-ethyl)-3,4-dihydroxy-5H-furan-2-one 
• 490-83-5 dehydro-L-ascorbic acid 
• 490-83-5 L-dehydroascorbic acid 
• 130233-86-2 Helioscopinin A 
• 130233-87-3 Helioscopin B 
• 1129294-89-8 isoascorbic acid 

Relevant articles and documents

Oxidation reactions of thymol: A pulse radiolysis and theoretical study

The reactions of ?OH and O?-, with thymol, a monoterpene phenol and an antioxidant, were studied by pulse radiolysis technique and DFT calculations at B3LYP/6-31+G(d,p) level of theory. Thymol was found to efficiently scavenge OH radicals (k = 8.1 × 109 dm3 mol-1 s-1) to produce reducing adduct radicals, with an absorption maximum at 330 nm and oxidizing phenoxyl radicals, with absorption maxima at 390 and 410 nm. A major part of these adduct radicals was found to undergo water elimination, leading to phenoxyl radicals, and the process was catalyzed by OH- (or Na2HPO4). The rate of reaction of O?- with thymol was found to be comparatively low (k = 1.1 × 109 dm3 mol -1 s-1), producing H abstracted species of thymol as well as phenoxyl radicals. Further, these phenoxyl radicals of thymol were found to be repaired by ascorbate (k = 2.1 × 108 dm3 mol -1 s-1). To support the interpretation of the experimental results, DFT calculations were carried out. The transients (both adducts and H abstracted species) have been optimized in gas phase at B3LYP/6-31+G(d,p) level of calculation. The relative energy values and thermodynamic stability suggests that the ortho adduct (C6-OH adduct) to be most stable in the reaction of thymol with OH radicals, which favors the water elimination. However, theoretical calculations showed that C4 atom in thymol (para position) can also be the reaction center as it is the main contributor of HOMO. The absorption maxima (λmax) calculated from time-dependent density functional theory (TDDFT) for these transient species were close to those obtained experimentally. Finally, the redox potential value of thymol?/ thymol couple (0.98 V vs NHE) obtained by cyclic voltammetry is less than those of physiologically important oxidants, which reveals the antioxidant capacity of thymol, by scavenging these oxidants. The repair of the phenoxyl radicals of thymol with ascorbate together with the redox potential value makes it a potent antioxidant with minimum pro-oxidant effects.

Outer-Sphere Electron-Transfer Reactions of Ascorbate Anions

Rate constants for the one-electron oxidation of ascorbate dianion (A2-) by bis(terpyridine)cobalt(III) ion (8.5*106 dm3 mol-1 s-1) and pentaammine(pyridine)ruthenium(III) ion (6.0*109 dm3 mol-1 s-1), and of the monoanion (HA-) by tetraammine(bipyridine)ruthenium(III) ion (2.1*105 dm3 mol-1 s-1) have been determined in aqueous solution at 25 deg C and ionic strength 0.1 (NaNO3 or NaClO4).It is shown that these rate constants, and other published rate constants for oxidation of HA- and A2-, are consistent with the Marcus cross relation, on the assumption that the self-exchange rate constants for both the HA-/HA. and A2-/A-. couples are 106 dm3 mol-1 s-1.One-electron redox potentials for the ascorbate/dehydroascorbate system have been derived from scattered literature data.