L-Dehydroascorbic acid | CAS#490-83-5 | cell death inducer for KRAS and BRAF mutants

MedKoo Cat#: 561704 | Name: L-Dehydroascorbic acid

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

L-Dehydroascorbic acid is the oxidized form of L-Ascorbic acid. It selectively induces cell death in KRAS and BRAF mutant cells in vitro.

Chemical Structure

L-Dehydroascorbic acid

CAS#490-83-5

Theoretical Analysis

MedKoo Cat#: 561704

Name: L-Dehydroascorbic acid

CAS#: 490-83-5

Chemical Formula: C6H6O6

Exact Mass: 174.0164

Molecular Weight: 174.11

Elemental Analysis: C, 41.39; H, 3.47; O, 55.13

Price and Availability

Size	Price	Availability
250mg	USD 285.00	2 Weeks
1g	USD 565.00	2 Weeks
5g	USD 950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

L-Dehydroascorbic acid; L Dehydroascorbic acid;

IUPAC/Chemical Name

L-threo-2,3-Hexodiulosonic acid gamma-lactone

InChi Key

SBJKKFFYIZUCET-JLAZNSOCSA-N

InChi Code

InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1

SMILES Code

O[C@@H](CO)[C@@H]1C(C(C(O1)=O)=O)=O

Appearance

Solid powder

Purity

>95% (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

>2 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

View handling instruction

Biological target:

Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke.

In vitro activity:

l-Dehydroascorbic acid (DHA), an oxidized form of AsA, necessitated the presence of 25-50 μM DTT or sub-millimolar concentrations of GSH and NAC for the scavenging of hydroxyl radicals and failed to scavenge hydroxyl radicals by itself. These results suggest that the redox cycling of AsA/DHA via thiols and cellular AsA metabolism are important processes to be considered while applying NTP to cells and tissues. Reference: Arch Biochem Biophys. 2019 Jul 15;669:87-95. https://pubmed.ncbi.nlm.nih.gov/31153952/

In vivo activity:

Reversible or permanent focal cerebral ischemia was created by intraluminal middle cerebral artery occlusion in mice treated with vehicle, AA, or DHA (L-Dehydroascorbic acid) (40, 250, or 500 mg/kg), either before or after ischemia. Given before ischemia, DHA caused dose-dependent increases in postreperfusion cerebral blood flow, with reductions in neurological deficit and mortality. In reperfused cerebral ischemia, mean infarct volume was reduced from 53% and 59% in vehicle- and AA-treated animals, respectively, to 15% in 250 mg/kg DHA-treated animals (P < 0.05). Reference: Proc Natl Acad Sci U S A. 2001 Sep 25;98(20):11720-4. https://pubmed.ncbi.nlm.nih.gov/11573006/

	Solvent	mg/mL	mM
Solubility
	DMSO	31.7	181.88
	DMSO:PBS (pH 7.2) (1:5)	0.2	0.92
	Water	5.0	28.72

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 174.11 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.

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. Okazaki Y, Tanaka H, Hori M, Toyokuni S. l-Dehydroascorbic acid recycled by thiols efficiently scavenges non-thermal plasma-induced hydroxyl radicals. Arch Biochem Biophys. 2019 Jul 15;669:87-95. doi: 10.1016/j.abb.2019.05.019. Epub 2019 May 31. PMID: 31153952. 2. Yun J, Mullarky E, Lu C, Bosch KN, Kavalier A, Rivera K, Roper J, Chio II, Giannopoulou EG, Rago C, Muley A, Asara JM, Paik J, Elemento O, Chen Z, Pappin DJ, Dow LE, Papadopoulos N, Gross SS, Cantley LC. Vitamin C selectively kills KRAS and BRAF mutant colorectal cancer cells by targeting GAPDH. Science. 2015 Dec 11;350(6266):1391-6. doi: 10.1126/science.aaa5004. Epub 2015 Nov 5. PMID: 26541605; PMCID: PMC4778961. 3. Liu Y, Huang P, Li Z, Xu C, Wang H, Jia B, Gong A, Xu M. Vitamin C Sensitizes Pancreatic Cancer Cells to Erastin-Induced Ferroptosis by Activating the AMPK/Nrf2/HMOX1 Pathway. Oxid Med Cell Longev. 2022 Jul 19;2022:5361241. doi: 10.1155/2022/5361241. PMID: 35915609; PMCID: PMC9338737. 4. Huang J, Agus DB, Winfree CJ, Kiss S, Mack WJ, McTaggart RA, Choudhri TF, Kim LJ, Mocco J, Pinsky DJ, Fox WD, Israel RJ, Boyd TA, Golde DW, Connolly ES Jr. Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke. Proc Natl Acad Sci U S A. 2001 Sep 25;98(20):11720-4. doi: 10.1073/pnas.171325998. PMID: 11573006; PMCID: PMC58796.

In vitro protocol:

In vivo protocol:

1. Liu Y, Huang P, Li Z, Xu C, Wang H, Jia B, Gong A, Xu M. Vitamin C Sensitizes Pancreatic Cancer Cells to Erastin-Induced Ferroptosis by Activating the AMPK/Nrf2/HMOX1 Pathway. Oxid Med Cell Longev. 2022 Jul 19;2022:5361241. doi: 10.1155/2022/5361241. PMID: 35915609; PMCID: PMC9338737. 2. Huang J, Agus DB, Winfree CJ, Kiss S, Mack WJ, McTaggart RA, Choudhri TF, Kim LJ, Mocco J, Pinsky DJ, Fox WD, Israel RJ, Boyd TA, Golde DW, Connolly ES Jr. Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke. Proc Natl Acad Sci U S A. 2001 Sep 25;98(20):11720-4. doi: 10.1073/pnas.171325998. PMID: 11573006; PMCID: PMC58796.

1: Frikke-Schmidt H, Tveden-Nyborg P, Lykkesfeldt J. L-dehydroascorbic acid can substitute l-ascorbic acid as dietary vitamin C source in guinea pigs. Redox Biol. 2016 Apr;7:8-13. doi: 10.1016/j.redox.2015.11.003. Epub 2015 Nov 21. PubMed PMID: 26609560; PubMed Central PMCID: PMC4683385. 2: Hosta-Rigau L, York-Duran MJ, Zhang Y, Goldie KN, Städler B. Confined multiple enzymatic (cascade) reactions within poly(dopamine)-based capsosomes. ACS Appl Mater Interfaces. 2014 Aug 13;6(15):12771-9. doi: 10.1021/am502743z. Epub 2014 Jul 9. PubMed PMID: 24968314. 3: Kimura M, Moteki H, Uchida M, Natsume H, Ogihara M. L-ascorbic acid- and L-ascorbic acid 2-glucoside accelerate in vivo liver regeneration and lower serum alanine aminotransaminase activity in 70% partially hepatectomized rats. Biol Pharm Bull. 2014;37(4):597-603. PubMed PMID: 24818255. 4: Szarka A, Lőrincz T. [Cellular and intracellular transport of vitamin C. The physiologic aspects]. Orv Hetil. 2013 Oct 20;154(42):1651-6. doi: 10.1556/OH.2013.29712. Review. Hungarian. PubMed PMID: 24121217. 5: Latocha P, Wołosiak R, Worobiej E, Krupa T. Clonal differences in antioxidant activity and bioactive constituents of hardy kiwifruit (Actinidia arguta) and its year-to-year variability. J Sci Food Agric. 2013 Apr;93(6):1412-9. doi: 10.1002/jsfa.5909. Epub 2012 Oct 15. PubMed PMID: 23070974. 6: Lee YC, Huang HY, Chang CJ, Cheng CH, Chen YT. Mitochondrial GLUT10 facilitates dehydroascorbic acid import and protects cells against oxidative stress: mechanistic insight into arterial tortuosity syndrome. Hum Mol Genet. 2010 Oct 1;19(19):3721-33. doi: 10.1093/hmg/ddq286. Epub 2010 Jul 16. PubMed PMID: 20639396. 7: Montel-Hagen A, Sitbon M, Taylor N. Erythroid glucose transporters. Curr Opin Hematol. 2009 May;16(3):165-72. doi: 10.1097/MOH.0b013e328329905c. Review. PubMed PMID: 19346941. 8: Montel-Hagen A, Kinet S, Manel N, Mongellaz C, Prohaska R, Battini JL, Delaunay J, Sitbon M, Taylor N. Erythrocyte Glut1 triggers dehydroascorbic acid uptake in mammals unable to synthesize vitamin C. Cell. 2008 Mar 21;132(6):1039-48. doi: 10.1016/j.cell.2008.01.042. PubMed PMID: 18358815. 9: Konings EJ; Committee on Food Nutrition. Water-soluble vitamins. J AOAC Int. 2006 Jan-Feb;89(1):285-8. PubMed PMID: 16512258. 10: Elmore AR. Final report of the safety assessment of L-Ascorbic Acid, Calcium Ascorbate, Magnesium Ascorbate, Magnesium Ascorbyl Phosphate, Sodium Ascorbate, and Sodium Ascorbyl Phosphate as used in cosmetics. Int J Toxicol. 2005;24 Suppl 2:51-111. Review. PubMed PMID: 16154915. 11: Nishiyama I, Yamashita Y, Yamanaka M, Shimohashi A, Fukuda T, Oota T. Varietal difference in vitamin C content in the fruit of kiwifruit and other actinidia species. J Agric Food Chem. 2004 Aug 25;52(17):5472-5. PubMed PMID: 15315387. 12: Reihl O, Lederer MO, Schwack W. Characterization and detection of lysine-arginine cross-links derived from dehydroascorbic acid. Carbohydr Res. 2004 Feb 25;339(3):483-91. PubMed PMID: 15013385. 13: Argirov OK, Lin B, Olesen P, Ortwerth BJ. Isolation and characterization of a new advanced glycation endproduct of dehydroascorbic acid and lysine. Biochim Biophys Acta. 2003 Mar 17;1620(1-3):235-44. PubMed PMID: 12595094. 14: Gil-Izquierdo A, Gil MI, Ferreres F. Effect of processing techniques at industrial scale on orange juice antioxidant and beneficial health compounds. J Agric Food Chem. 2002 Aug 28;50(18):5107-14. PubMed PMID: 12188615. 15: Hirai K, Pan JH, Shui YB, Simamura E, Shimada H, Kanamaru T, Koyama J. Alpha-tocopherol protects cultured human cells from the acute lethal cytotoxicity of dioxin. Int J Vitam Nutr Res. 2002 May;72(3):147-53. PubMed PMID: 12098882. 16: Ogiri Y, Sun F, Hayami S, Fujimura A, Yamamoto K, Yaita M, Kojo S. Very low vitamin C activity of orally administered L-dehydroascorbic acid. J Agric Food Chem. 2002 Jan 2;50(1):227-9. PubMed PMID: 11754572. 17: Abou-Seif MA, Rabia A, Nasr M. Antioxidant status, erythrocyte membrane lipid peroxidation and osmotic fragility in malignant lymphoma patients. Clin Chem Lab Med. 2000 Aug;38(8):737-42. PubMed PMID: 11071066. 18: Rönner B, Lerche H, Bergmüller W, Freilinger C, Severin T, Pischetsrieder M. Formation of tetrahydro-beta-carbolines and beta-carbolines during the reaction of L-tryptophan with D-glucose. J Agric Food Chem. 2000 Jun;48(6):2111-6. PubMed PMID: 10888507. 19: Bognár A, Daood HG. Simple in-line postcolumn oxidation and derivatization for the simultaneous analysis of ascorbic and dehydroascorbic acids in foods. J Chromatogr Sci. 2000 Apr;38(4):162-8. PubMed PMID: 10766483. 20: Seidel W, Pischetsrieder M. Immunochemical detection of N2-[1-(1-carboxy)ethyl]guanosine, an advanced glycation end product formed by the reaction of DNA and reducing sugars or L-ascorbic acid in vitro. Biochim Biophys Acta. 1998 Nov 27;1425(3):478-84. PubMed PMID: 9838211.