MDN99781
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MedKoo CAT#: 462929

CAS#: 129499-78-1

Description: MDN99781, also known as 2-O-α-D-Glucopyranosyl-L-ascorbic acid is a glucosylated derivative of L-ascorbic acid that has antioxidant and radioprotective activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl radicals in a cell-free assay. AA-2G inhibits γ-radiation-induced cell death in CHO-10B2 and radiosensitive xrs5 cells, as well as UVC- or broadband UVB-induced cell death in CHO-10B2 and UV-sensitive UV135 cells. It is hydrolyzed to ascorbic acid by α-glucosidase and increases serum levels of ascorbic acid in rats and guinea pigs when administered orally at doses of 19.2 and 96 mg/animal, respectively. AA-2G reverses weight loss and inhibits subcutaneous hemorrhage in guinea pigs fed a vitamin C-deficient diet. This product has no formal name at the moment. For the convenience of communication, a temporary code name was therefore proposed according to MedKoo Chemical Nomenclature (see web page: https://www.medkoo.com/page/naming).

Chemical Structure

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MDN99781
CAS# 129499-78-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 462929
Name: MDN99781
CAS#: 129499-78-1
Chemical Formula: C12H18O11
Exact Mass: 338.08
Molecular Weight: 338.265
Elemental Analysis: C, 42.61; H, 5.36; O, 52.03

Price and Availability

Size Price Availability Quantity
5g USD 250 2 Weeks
25g USD 450 2 Weeks
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Synonym: AA-2G; Asc2G; Ascorbic Acid 2-glucoside; MDN99781; MDN 99781; MDN-99781

IUPAC/Chemical Name: (R)-5-((S)-1,2-dihydroxyethyl)-4-hydroxy-3-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)furan-2(5H)-one

InChi Key: MLSJBGYKDYSOAE-DCWMUDTNSA-N

InChi Code: InChI=1S/C12H18O11/c13-1-3(15)9-8(19)10(11(20)22-9)23-12-7(18)6(17)5(16)4(2-14)21-12/h3-7,9,12-19H,1-2H2/t3-,4+,5+,6-,7+,9+,12+/m0/s1

SMILES Code: OC[C@@H](O[C@@H]1OC2=C([C@]([H])(OC2=O)[C@@H](O)CO)O)[C@@H](O)[C@H](O)[C@H]1O

Appearance: Solid powder

Purity: >97% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: MDN99781, also known as 2-O-α-D-Glucopyranosyl-L-ascorbic acid is a glucosylated derivative of L-ascorbic acid that has antioxidant and radioprotective activities.
In vitro activity: Pretreatment with DMSO, AA, and AA2G (MDN99781) showed comparative protective effects in CHO wild type and radiosensitive xrs5 cells for cell death against ionizing radiation with reducing the number of radiation-induced DNA damages. These results suggest that AA2G protects cells from radiation by acting as a radical scavenger to reduce initial DNA damage, as well as protecting cells from certain UVB wavelengths by filtration. Reference: Genes (Basel). 2020 Feb 25;11(3):238. https://pubmed.ncbi.nlm.nih.gov/32106443/
In vivo activity: AA2G (MDN99781) treatment reduced the intestinal damage (shortening of villi) but did not reduce antitumor effectiveness of radiotherapy against bladder tumors. AA2G treatment significantly increased CD163+/CD68+ macrophage ratio in the ilea of rats after pelvic irradiation in comparison to the sham irradiated control rats. AA2G treatment increased, albeit not significantly, the CD163+/CD68+ macrophage ratio in the irradiated bladders relative to the control irradiated rats. Reference: Int J Radiat Biol. 2022;98(5):942-957. https://pubmed.ncbi.nlm.nih.gov/34871138/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 34.5 101.99
PBS (pH 7.2) 1.0 2.96
Water 96.5 285.28

Preparing Stock Solutions

The following data is based on the product molecular weight 338.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Yi Y, Wu M, Zhou X, Xiong M, Tan Y, Yu H, Liu Z, Wu Y, Zhang Q. Ascorbic acid 2-glucoside preconditioning enhances the ability of bone marrow mesenchymal stem cells in promoting wound healing. Stem Cell Res Ther. 2022 Mar 21;13(1):119. doi: 10.1186/s13287-022-02797-0. PMID: 35313962; PMCID: PMC8935805. 2. Maeda J, Allum AJ, Mussallem JT, Froning CE, Haskins AH, Buckner MA, Miller CD, Kato TA. Ascorbic Acid 2-Glucoside Pretreatment Protects Cells from Ionizing Radiation, UVC, and Short Wavelength of UVB. Genes (Basel). 2020 Feb 25;11(3):238. doi: 10.3390/genes11030238. PMID: 32106443; PMCID: PMC7140853. 3. Ito Y, Yamamoto T, Miyai K, Take J, Scherthan H, Rommel A, Eder S, Steinestel K, Rump A, Port M, Shinomiya N, Kinoshita M. Ascorbic acid-2 glucoside mitigates intestinal damage during pelvic radiotherapy in a rat bladder tumor model. Int J Radiat Biol. 2022;98(5):942-957. doi: 10.1080/09553002.2021.2009145. Epub 2021 Dec 6. PMID: 34871138. 4. Miura K, Tai A. 2-O-α-D-Glucopyranosyl-l-ascorbic acid as an antitumor agent for infusion therapy. Biochem Biophys Rep. 2017 Apr 22;10:232-236. doi: 10.1016/j.bbrep.2017.04.014. PMID: 28955751; PMCID: PMC5614674.
In vitro protocol: 1. Yi Y, Wu M, Zhou X, Xiong M, Tan Y, Yu H, Liu Z, Wu Y, Zhang Q. Ascorbic acid 2-glucoside preconditioning enhances the ability of bone marrow mesenchymal stem cells in promoting wound healing. Stem Cell Res Ther. 2022 Mar 21;13(1):119. doi: 10.1186/s13287-022-02797-0. PMID: 35313962; PMCID: PMC8935805. 2. Maeda J, Allum AJ, Mussallem JT, Froning CE, Haskins AH, Buckner MA, Miller CD, Kato TA. Ascorbic Acid 2-Glucoside Pretreatment Protects Cells from Ionizing Radiation, UVC, and Short Wavelength of UVB. Genes (Basel). 2020 Feb 25;11(3):238. doi: 10.3390/genes11030238. PMID: 32106443; PMCID: PMC7140853.
In vivo protocol: 1. Ito Y, Yamamoto T, Miyai K, Take J, Scherthan H, Rommel A, Eder S, Steinestel K, Rump A, Port M, Shinomiya N, Kinoshita M. Ascorbic acid-2 glucoside mitigates intestinal damage during pelvic radiotherapy in a rat bladder tumor model. Int J Radiat Biol. 2022;98(5):942-957. doi: 10.1080/09553002.2021.2009145. Epub 2021 Dec 6. PMID: 34871138. 2. Miura K, Tai A. 2-O-α-D-Glucopyranosyl-l-ascorbic acid as an antitumor agent for infusion therapy. Biochem Biophys Rep. 2017 Apr 22;10:232-236. doi: 10.1016/j.bbrep.2017.04.014. PMID: 28955751; PMCID: PMC5614674.

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1: Maekawa T, Uchida T, Nakata-Horiuchi Y, Kobayashi H, Kawauchi S, Kinoshita M, Saitoh D, Sato S. Oral ascorbic acid 2-glucoside prevents coordination disorder induced via laser-induced shock waves in rat brain. PLoS One. 2020 Apr 2;15(4):e0230774. doi: 10.1371/journal.pone.0230774. PMID: 32240226; PMCID: PMC7117653.

2: Richardson AT, Cho J, McGhie TK, Larsen DS, Schaffer RJ, Espley RV, Perry NB. Discovery of a stable vitamin C glycoside in crab apples (Malus sylvestris). Phytochemistry. 2020 May;173:112297. doi: 10.1016/j.phytochem.2020.112297. Epub 2020 Feb 15. PMID: 32070800.

3: Tao X, Su L, Wang L, Chen X, Wu J. Improved production of cyclodextrin glycosyltransferase from Bacillus stearothermophilus NO2 in Escherichia coli via directed evolution. Appl Microbiol Biotechnol. 2020 Jan;104(1):173-185. doi: 10.1007/s00253-019-10249-8. Epub 2019 Nov 22. PMID: 31758236.

4: Gérard V, Ay E, Graff B, Morlet-Savary F, Galopin C, Mutilangi W, Lalevée J. Ascorbic Acid Derivatives as Potential Substitutes for Ascorbic Acid To Reduce Color Degradation of Drinks Containing Ascorbic Acid and Anthocyanins from Natural Extracts. J Agric Food Chem. 2019 Oct 30;67(43):12061-12071. doi: 10.1021/acs.jafc.9b05049. Epub 2019 Oct 17. PMID: 31588743.

5: Li Y, Li Z, He X, Chen L, Cheng Y, Jia H, Yan M, Chen K. Characterisation of a Thermobacillus sucrose phosphorylase and its utility in enzymatic synthesis of 2-O-α-d-glucopyranosyl-l- ascorbic acid. J Biotechnol. 2019 Nov 10;305:27-34. doi: 10.1016/j.jbiotec.2019.08.018. Epub 2019 Aug 27. PMID: 31470069.

6: Zhang H, Wang Z, Yang X, Li ZL, Sun L, Ma J, Jiang H. The determination of α-glucosidase activity through a nano fluorescent sensor of F-PDA-CoOOH. Anal Chim Acta. 2019 Nov 8;1080:170-177. doi: 10.1016/j.aca.2019.07.014. Epub 2019 Jul 9. PMID: 31409467.

7: Shi M, Cen Y, Xu G, Wei F, Xu X, Cheng X, Chai Y, Sohail M, Hu Q. Ratiometric fluorescence monitoring of α-glucosidase activity based on oxidase-like property of MnO2 nanosheet and its application for inhibitor screening. Anal Chim Acta. 2019 Oct 24;1077:225-231. doi: 10.1016/j.aca.2019.05.037. Epub 2019 May 21. PMID: 31307713.

8: Tao X, Su L, Wu J. Current studies on the enzymatic preparation 2-O-α-d- glucopyranosyl-l-ascorbic acid with cyclodextrin glycosyltransferase. Crit Rev Biotechnol. 2019 Mar;39(2):249-257. doi: 10.1080/07388551.2018.1531823. Epub 2018 Dec 18. PMID: 30563366.

9: Haskins AH, Buglewicz DJ, Hirakawa H, Fujimori A, Aizawa Y, Kato TA. Palmitoyl ascorbic acid 2-glucoside has the potential to protect mammalian cells from high-LET carbon-ion radiation. Sci Rep. 2018 Sep 14;8(1):13822. doi: 10.1038/s41598-018-31747-1. PMID: 30218013; PMCID: PMC6138748.

10: Jiang Y, Zhou J, Wu R, Xin F, Zhang W, Fang Y, Ma J, Dong W, Jiang M. Heterologous expression of cyclodextrin glycosyltransferase from Paenibacillus macerans in Escherichia coli and its application in 2-O-α-D-glucopyranosyl-L- ascorbic acid production. BMC Biotechnol. 2018 Aug 31;18(1):53. doi: 10.1186/s12896-018-0463-9. PMID: 30170578; PMCID: PMC6119282.

11: Tao X, Wang T, Su L, Wu J. Enhanced 2- O-α-d-Glucopyranosyl-l-ascorbic Acid Synthesis through Iterative Saturation Mutagenesis of Acceptor Subsite Residues in Bacillus stearothermophilus NO2 Cyclodextrin Glycosyltransferase. J Agric Food Chem. 2018 Aug 29;66(34):9052-9060. doi: 10.1021/acs.jafc.8b03080. Epub 2018 Aug 17. PMID: 30091914.

12: Sampaio BFB, Nogueira BG, Souza MIL, Silva EVDCE, Zúccari CESN. Effects of ascorbic acid 2-glucoside and alpha-tocopherol on the characteristics of equine spermatozoa stored at 5°C. Anim Sci J. 2018 Oct;89(10):1415-1423. doi: 10.1111/asj.12944. Epub 2018 Jul 24. PMID: 30043478.

13: Miura K, Morishita Y, Matsuno H, Aota Y, Ito H, Tai A. Anti-Allergic Activity of Monoacylated Ascorbic Acid 2-Glucosides. Molecules. 2017 Dec 12;22(12):2202. doi: 10.3390/molecules22122202. PMID: 29231858; PMCID: PMC6149712.

14: Qin Y, Yang S, Xu J, Xia C, Li X, An L, Tian J. Deep insemination with sex- sorted Cashmere goat sperm processed in the presence of antioxidants. Reprod Domest Anim. 2018 Feb;53(1):11-19. doi: 10.1111/rda.13045. Epub 2017 Dec 3. PMID: 29205543.

15: Chen X, Liu R, Liu X, Xu C, Wang X. L-ascorbic Acid-2-Glucoside inhibits Helicobacter pylori-induced apoptosis through mitochondrial pathway in Gastric Epithelial cells. Biomed Pharmacother. 2018 Jan;97:75-81. doi: 10.1016/j.biopha.2017.10.030. Epub 2017 Nov 6. PMID: 29080461.

16: Miura K, Tai A. 2-O-α-D-Glucopyranosyl-l-ascorbic acid as an antitumor agent for infusion therapy. Biochem Biophys Rep. 2017 Apr 22;10:232-236. doi: 10.1016/j.bbrep.2017.04.014. PMID: 28955751; PMCID: PMC5614674.

17: Tai A, Iomori A, Ito H. Structural evidence for the DPPH radical-scavenging mechanism of 2-O-α-d-glucopyranosyl-l-ascorbic acid. Bioorg Med Chem. 2017 Oct 15;25(20):5303-5310. doi: 10.1016/j.bmc.2017.07.044. Epub 2017 Jul 28. PMID: 28789909.

18: Gudiminchi RK, Nidetzky B. Walking a Fine Line with Sucrose Phosphorylase: Efficient Single-Step Biocatalytic Production of l-Ascorbic Acid 2-Glucoside from Sucrose. Chembiochem. 2017 Jul 18;18(14):1387-1390. doi: 10.1002/cbic.201700215. Epub 2017 Jun 5. PMID: 28426168.

19: Chen S, Xiong Y, Su L, Wang L, Wu J. Position 228 in Paenibacillus macerans cyclodextrin glycosyltransferase is critical for 2-O-d-glucopyranosyl-l-ascorbic acid synthesis. J Biotechnol. 2017 Apr 10;247:18-24. doi: 10.1016/j.jbiotec.2017.02.011. Epub 2017 Feb 17. PMID: 28219734.

20: Roure R, Nollent V, Dayan L, Camel E, Bertin C. A Double-Blind, 12-Week Study to Evaluate the Antiaging Efficacy of a Cream Containing the NFκB Inhibitor 4-Hexyl-1, 3-Phenylenediol and Ascorbic Acid-2 Glucoside in Adult Females. J Drugs Dermatol. 2016 Jun 1;15(6):750-8. PMID: 27272084.