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129499-78-1,MFCD14525839
Catalog No.:AA009BHW

129499-78-1 | 2-O-Alpha-d-glucopyranosyl-l-ascorbic acid

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1g
97%
in stock  
$11.00   $8.00
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5g
97%
in stock  
$15.00   $11.00
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10g
97%
in stock  
$18.00   $13.00
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25g
97%
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$44.00   $31.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA009BHW
Chemical Name:
2-O-Alpha-d-glucopyranosyl-l-ascorbic acid
CAS Number:
129499-78-1
Molecular Formula:
C12H18O11
Molecular Weight:
338.2647
MDL Number:
MFCD14525839
SMILES:
OC[C@@H]([C@H]1OC(=O)C(=C1O)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O
Properties
Computed Properties
 
Complexity:
478  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
7  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
7  
Rotatable Bond Count:
5  
XLogP3:
-3.1  

Upstream Synthesis Route

[1]AgriculturalandBiologicalChemistry,1991,vol.55,#7,p.1751-1756

[2]ACSCatalysis,2016,vol.6,#3,p.1606-1615

[1]Patent:EP2653475,2013,A1,.Locationinpatent:Paragraph0125;0126;0127;0128

[1]JournalofMolecularCatalysisB:Enzymatic,2013,vol.92,p.19-23

[1]JournalofMolecularCatalysisB:Enzymatic,2013,vol.92,p.19-23

[1]JournalofMolecularCatalysisB:Enzymatic,2013,vol.92,p.19-23

Downstream Synthesis Route

[1]ChemicalandPharmaceuticalBulletin,1990,vol.38,p.3020-3023

[1]AgriculturalandBiologicalChemistry,1991,vol.55,p.1751-1756

[2]ACSCatalysis,2016,vol.6,p.1606-1615

123-20-6    129499-78-1   
6-O-butyryl-2-O-α-D-glucopyranosyl-L-ascorbicacid 

[1]ChemicalandPharmaceuticalBulletin,2001,vol.49,p.1047-1049

3050-69-9    129499-78-1   
2-O-α-D-glucopyranosyl-6-O-hexanoyl-L-ascorbicacid 

[1]ChemicalandPharmaceuticalBulletin,2001,vol.49,p.1047-1049

Literature

Title: Fractional carbon dioxide laser treatment to enhance skin permeation of ascorbic acid 2-glucoside with minimal skin disruption.

Journal: Dermatologic surgery : official publication for American Society for Dermatologic Surgery [et al.] 20120801

Title: Commentary: fractional laser resurfacing to enhance skin permeation.

Journal: Dermatologic surgery : official publication for American Society for Dermatologic Surgery [et al.] 20120801

Title: Evaluation of the antioxidative capability of commonly used antioxidants in dermocosmetics by in vivo detection of protein carbonylation in human stratum corneum.

Journal: Journal of photochemistry and photobiology. B, Biology 20120702

Title: Functions, applications and production of 2-O-D-glucopyranosyl-L-ascorbic acid.

Journal: Applied microbiology and biotechnology 20120701

Title: Signal transduction pathway for L-ascorbic acid- and L-ascorbic acid 2-glucoside-induced DNA synthesis and cell proliferation in primary cultures of adult rat hepatocytes.

Journal: European journal of pharmacology 20120515

Title: Radical-regulating and antiviral properties of ascorbic acid and its derivatives.

Journal: Bioorganic & medicinal chemistry letters 20120401

Title: Anti-oxidative and anti-aging activities of 2-O-α-glucopyranosyl-L-ascorbic acid on human dermal fibroblasts.

Journal: European journal of pharmacology 20120115

Title: Regioselective monoacylation of 2-O-α-D-glucopyranosyl-L-ascorbic acid by a polymer catalyst in N,N-dimethylformamide.

Journal: Carbohydrate research 20111108

Title: Skin pretreatment with lasers promotes the transdermal delivery of vitamin C derivatives.

Journal: Lasers in medical science 20110501

Title: Supplementation of cryomedium with ascorbic acid-2-glucoside (AA2G) improves human sperm post-thaw motility.

Journal: Fertility and sterility 20110501

Title: Mass spectrometric stereoisomeric differentiation between α- and β-ascorbic acid 2-O-glucosides. Experimental and density functional theory study.

Journal: Rapid communications in mass spectrometry : RCM 20110330

Title: Monoacylation of 2-O-alpha-D-glucopyranosyl-L-ascorbic acid by protease in N,N-dimethylformamide with low water content.

Journal: Carbohydrate research 20100816

Title: Intramolecular acyl migration and enzymatic hydrolysis of a novel monoacylated ascorbic acid derivative, 6-O-dodecanoyl-2-O-alpha-d-glucopyranosyl-L-ascorbic acid.

Journal: Bioorganic & medicinal chemistry 20100815

Title: Ascorbic acid 2-glucocide reduces micronucleus induction in distant splenic T lymphocytes following head irradiation.

Journal: Mutation research 20100101

Title: Protease-catalyzed monoacylation of 2-O-α-D-glucopyranosyl-L-ascorbic acid in three solvent systems.

Journal: Bioscience, biotechnology, and biochemistry 20100101

Title: Evaluation of depigmenting activity by 8-hydroxydaidzein in mouse B16 melanoma cells and human volunteers.

Journal: International journal of molecular sciences 20091001

Title: Bioavailability of 2-O-alpha-D-glucopyranosyl-L-ascorbic acid as ascorbic acid in healthy humans.

Journal: Nutrition (Burbank, Los Angeles County, Calif.) 20090601

Title: Promotion of IL-4- and IL-5-dependent differentiation of anti-mu-primed B cells by ascorbic acid 2-glucoside.

Journal: Immunology letters 20090221

Title: Effects of ascorbic acid on gingival melanin pigmentation in vitro and in vivo.

Journal: Journal of periodontology 20090201

Title: [Course in development of a stable vitamin C derivative (AA-2G)].

Journal: Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20080901

Title: Improvement of the post-thaw qualities of Okinawan native pig spermatozoa frozen in an extender supplemented with ascorbic acid 2-O-alpha-glucoside.

Journal: Cryobiology 20080801

Title: Inhibition of free radical-induced erythrocyte hemolysis by 2-O-substituted ascorbic acid derivatives.

Journal: Free radical biology & medicine 20071015

Title: Determination of ascorbic acid and its related compounds in foods and beverages by hydrophilic interaction liquid chromatography.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070615

Title: Transglucosylation of ascorbic acid to ascorbic acid 2-glucoside by a recombinant sucrose phosphorylase from Bifidobacterium longum.

Journal: Biotechnology letters 20070401

Title: 2-O-alpha-D-glucopyranosyl-L-ascorbic acid scavenges 1,1-diphenyl-2-picrylhydrazyl radicals via a covalent adduct formation.

Journal: Bioscience, biotechnology, and biochemistry 20070301

Title: Application of ascorbic acid 2-glucoside as a solubilizing agent for clarithromycin: solubilization and nanoparticle formation.

Journal: International journal of pharmaceutics 20070222

Title: Combining high-performance liquid chromatography with on-line microdialysis sampling for the simultaneous determination of ascorbyl glucoside, kojic acid, and niacinamide in bleaching cosmetics.

Journal: Analytica chimica acta 20070102

Title: Suppressive effects of ascorbate derivatives on ultraviolet-B-induced injury in HaCaT human keratinocytes.

Journal: In vitro cellular & developmental biology. Animal 20040101

Title: Annexin V assay-proven anti-apoptotic effect of ascorbic acid 2-glucoside after cold ischemia/reperfusion injury in rat liver transplantation.

Journal: Acta medica Okayama 20031001

Title: pH-dependent long-term radical scavenging activity of AA-2G and 6-Octa-AA-2G against 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation.

Journal: Biological & pharmaceutical bulletin 20030901

Title: Enhancement of neurite outgrowth in PC12 cells stimulated with cyclic AMP and NGF by 6-acylated ascorbic acid 2-O-alpha-glucosides (6-Acyl-AA-2G), novel lipophilic ascorbate derivatives.

Journal: Biological & pharmaceutical bulletin 20030301

Title: Maintenance of cold-preserved porcine hepatocyte function with UW solution and ascorbic acid-2 glucoside.

Journal: Cell transplantation 20030101

Title: Long-term radical scavenging activity of AA-2G and 6-acyl-AA-2G against 1,1-diphenyl-2-picrylhydrazyl.

Journal: Biological & pharmaceutical bulletin 20021101

Title: Bioavailability of a series of novel acylated ascorbic acid derivatives, 6-O-acyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acids, as an ascorbic acid supplement in rats and guinea pigs.

Journal: Bioscience, biotechnology, and biochemistry 20020801

Title: Enhancement of developmental competence after in vitro fertilization of porcine oocytes by treatment with ascorbic acid 2-O-alpha-glucoside during in vitro maturation.

Journal: Biology of reproduction 20011201

Title: Protease-catalyzed monoacylation of 2-O-alpha-D-Glucopyranosyl-L-ascorbic acid in pyridine.

Journal: Chemical & pharmaceutical bulletin 20010801

Title: Radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl of ascorbic acid 2-glucoside (AA-2G) and 6-acyl-AA-2G.

Journal: Chemical & pharmaceutical bulletin 20010501

Title: Miura K, et al. 2-O-α-D-Glucopyranosyl-l-ascorbic acid as an antitumor agent for infusion therapy. Biochem Biophys Rep. 2017 Apr 22;10:232-236.

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