10504-35-5

Basic information

• Product Name: Xyloascorbic acid, D-
• Synonyms: D-Ascorbic acid (7CI, 8CI, 9CI);D-Lyxoascorbic acid;D-threo-Hex-2-enonic acid, γ-lactone;D-Xyloascorbic acid;Xyloascorbic acid, D-;(4S,5R)-2,3,4,5,6-Pentahydroxy-2-hexenoic acid 1,4-lactone;(S)-5-[(R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
• CAS NO: 10504-35-5
• Molecular Formula: C₆H₈O₆
• Molecular Weight: 176.1241
• Mol File: 10504-35-5.mol

Chemical Properties

• Boiling Point: 552.672 °C at 760 mmHg
• Flash Point: 238.199 °C
• Appearance: /
• Density: 1.954 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.711
• CAS DataBase Reference: Xyloascorbic acid, D-(CAS DataBase Reference)
• NIST Chemistry Reference: Xyloascorbic acid, D-(10504-35-5)
• EPA Substance Registry System: Xyloascorbic acid, D-(10504-35-5)

Safety Data

• Hazardous Substances Data: 10504-35-5(Hazardous Substances Data)

Usage

Uses

Used in Food and Beverage Industry:
Xyloascorbic acid, Dis used as a preservative and additive in the food and beverage industry to prevent oxidation and deterioration of products. Its antioxidant properties help maintain the freshness and quality of food items, extending their shelf life.
Used in Pharmaceutical Industry:
Xyloascorbic acid, Dmay have potential applications in the pharmaceutical industry due to its involvement in various biochemical processes in the body. Its antioxidant properties could contribute to the development of medications targeting specific health conditions.
Used in Cosmetics Industry:
Xyloascorbic acid, Dmay also find use in the cosmetics industry, where its antioxidant properties can be harnessed to develop skincare products. These products could potentially benefit from its ability to protect against oxidative stress and support skin health.

InChI:InChI=1/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m1/s1

Upstream product

• 67776-07-2 D-xylo-[2]hexulosonic acid methyl ester 
• 109214-36-0 D-lyxo-[2]hexulosonic acid methyl ester 
• 124890-18-2 mallojaponin 
• 124890-19-3 mallonin 
• 185675-56-3 (S)-3,4-Bis-benzyloxy-5-((2R,4R)-2-phenyl-[1,3]dioxolan-4-yl)-5H-furan-2-one 
• 185675-55-2 (S)-3,4-Bis-benzyloxy-5-((2S,4R)-2-phenyl-[1,3]dioxolan-4-yl)-5H-furan-2-one 
• 7732-18-5 water 
• 6322-07-2 D-gulono-1,4-lactone 
• 924-44-7 glyoxylic acid ethyl ester 
• 49653-17-0 ethyl 2-ethoxyglycolate 
• 16722-49-9 D-lyxo-2-hexulosonic acid 
• 89-65-6 isoascorbic acid 
• 21675-47-8 D-xylo-2-hexulosonic acid 
• 62624-30-0 ascorbic acid 

Downstream Products

• 62624-30-0 ascorbic acid 
• 15042-01-0 5-[2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-5H-furan-2-one 
• 130233-87-3 Helioscopin B 
• 130233-86-2 Helioscopinin A 
• 490-83-5 L-dehydroascorbic acid 
• 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 
• 490-83-5 dehydro-L-ascorbic acid 
• 1129294-89-8 5-(1,2-Dihydroxy-ethyl)-3,4-dihydroxy-5H-furan-2-one 
• 15667-21-7 D-erythronolactone 
• 1128-23-0 L-gulono-1,4-lactone 
• 15042-01-0 O-5,6-isopropylidene-L-(+)ascorbic acid 

Relevant articles and documents

An easy 'Filter-and-Separate' method for enantioselective separation and chiral sensing of substrates using a biomimetic homochiral polymer

We present a polyfluorene appended with protected l-glutamic acid that exhibited a reversible α-helix/β-sheet-like conformation and helical porous fibrous morphology mimicking the super-structure of proteins. The new homochiral polymer probe enabled efficient heterogeneous enantioselective separation and chiral sensing of a wide variety of substrates from their aqueous racemic mixture using an easy 'Filter-and-Separate' method.

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.

Organoalane-mediated isomerization of ascorbic and isoascorbic acid derivatives

Derivatives of L-ascorbic acid 2a, 10a/11a and D-isoascorbic acid 2b, 10b/11b, when treated with triisobutylaluminium, partly epimerize to give the corresponding derivatives of L-isoascorbic acid ent-2b, ent-10b or D-ascorbic acid ent-2a, ent-10a, ent-11a, respectively. Complete removal of the protecting groups is effected by hydrogenolysis of the benzylidene acetals ent-10 and ent-11a. This reaction leads to D-ascorbic acid ent-1a or L-isoascorbic acid ent-1b, respectively. Furthermore, the four acetonides 2 were converted by ozonolysis, transesterification and finally catalytic hydrogenation to the threonic and erythronic acid ketals 9. Copyright (C) Elsevier Science Ltd.

Tannins and related compounds. LXXXIV. Isolation and characterization of five new hydrolyzable tannins from the bark of Mallotus japonicus.

A chemical examination of the bark of Mallotus japonicus (Thunb.) Mueller-Arg. (Euphorbiaceae) has led to the isolation of five new hydrolyzable tannins (16-20), together with fourteen known tannins (1-14). On the basis of chemical and spectroscopic evidence, the structures of compounds 16 and 17 were established as 1,2-di-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-beta-D-glucose and 1-O-digalloyl-3,6-(R)-hexahydroxydiphenoyl-beta-D-glucose, respectively, while compounds 18 (mallojaponin) and 19 (mallonin) were shown to be 1-O-galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-bet a-D-glucose and 1-O-galloyl-2,4-elaeocarpusinoyl-beta-D-glucose. Compound 20 (mallotusinin) was characterized as a novel ellagitannin which possesses a unique 1,1'-(3,3',4,4'-tetrahydroxy)dibenzofurandicarboxyl group. On the other hand, examination of the leaves revealed the presence of hydrolyzable tannins (8-10, 12-15) all containing a beta-D-glucopyranose core with 1C4-conformation. Furthermore, the orientation of the valoneayl group in mallotinic acid (13) and mallotusinic acid (14), which had remained unclarified, was determined on the basis of 1H-13C shift correlation spectral analysis and chemical correlations.

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.

Electron Transfer Reactions of Halogenated Aliphatic Peroxyl Radicals: Measurement of Absolute Rate Constants by Pulse Radiolysis

The peroxyl radicals Cl3OO., Cl2CHOO., ClCH2OO., CH3OO., .OOCCl2CO2-, .OOCHClCO2-, .OOCH2CO2-, .OOCF2CO2-, and (CH3)2C(OH)CH2OO. have been generated in aqueous alcohol solutions by pulse radiolysis using the Brunel and Hahn-Meitner accelerators.The absolute rate constants of the one-electron transfer reactions of related aliphatic peroxyl radicals with ascorbate, promethazine, phenol, and tyrosine have been found to increase with increasing substitution of chlorine atoms.For the reaction of the radical Cl3CO2. and promethazine, at pH 6, k 6.0 +/- 0.4 x 108 l mol-1 s-1 has been measured.For the analogous reaction of the radical ClCH2O2., k 3.3 +/- 0.2 x 107 l mol-1 s-1 has been determined.