D-Erythrose | CAS#583-50-6

MedKoo Cat#: 407865 | Name: D-Erythrose

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Description:

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

D-Erythrose is an antitumor agent. D-Erythrose inhibits tumor growth in mice (in vivo). It is used to study the mechanisms of organic micro spherule formation and Maillard (glycation) reactions. D-erythrose significantly reduced the weight of the intraperitoneal tumor by 69.1%, markedly inhibited the development of ascites and increased tumor cell apoptosis, without any observed toxic effects. D-erythrose possesses antitumor activity against colon cancer.

Chemical Structure

D-Erythrose

CAS#583-50-6

Theoretical Analysis

MedKoo Cat#: 407865

Name: D-Erythrose

CAS#: 583-50-6

Chemical Formula: C4H8O4

Exact Mass: 120.0423

Molecular Weight: 120.10

Elemental Analysis: C, 40.00; H, 6.71; O, 53.28

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 285.00	2 Weeks
250mg	USD 550.00	2 Weeks

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Related CAS #

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Synonym

D-Erythrose; D-(-)-Erythrose; Erythrose

IUPAC/Chemical Name

(2R,3R)-2,3,4-trihydroxybutanal

InChi Key

YTBSYETUWUMLBZ-IUYQGCFVSA-N

InChi Code

InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1

SMILES Code

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

Appearance

To be determined

Purity

Syrup, ca 70% w/v, >75% dry wt. basis

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

Erythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and so is part of the aldose family. The natural isomer is D-erythrose. Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869), and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 120.10 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

1: Sousa CE, Ribeiro AM, Gil Fortes A, Cerqueira NM, Alves MJ. Total Facial Discrimination of 1,3-Dipolar Cycloadditions in a d-Erythrose 1,3-Dioxane Template: Computational Studies of a Concerted Mechanism. J Org Chem. 2017 Jan 20;82(2):982-991. doi: 10.1021/acs.joc.6b02518. Epub 2017 Jan 9. PubMed PMID: 28032997. 2: Szczepaniak M, Moc J. Anomerization reaction of bare and microhydrated d-erythrose via explicitly correlated coupled cluster approach. Two water molecules are optimal. J Comput Chem. 2017 Feb 15;38(5):288-303. doi: 10.1002/jcc.24680. Epub 2016 Nov 29. PubMed PMID: 27896831. 3: Kaufmann M, Mügge C, Kroh LW. Theory of the milieu dependent isomerisation dynamics of reducing sugars applied to d-erythrose. Carbohydr Res. 2015 Dec 11;418:89-97. doi: 10.1016/j.carres.2015.10.010. Epub 2015 Oct 30. PubMed PMID: 26580710. 4: Liu LL, Yi T, Zhao X. Antitumor effect of D-erythrose in an abdominal metastatic model of colon carcinoma. Oncol Lett. 2015 Feb;9(2):769-773. Epub 2014 Dec 3. PubMed PMID: 25621049; PubMed Central PMCID: PMC4301512. 5: Barbier T, Collard F, Zúñiga-Ripa A, Moriyón I, Godard T, Becker J, Wittmann C, Van Schaftingen E, Letesson JJ. Erythritol feeds the pentose phosphate pathway via three new isomerases leading to D-erythrose-4-phosphate in Brucella. Proc Natl Acad Sci U S A. 2014 Dec 16;111(50):17815-20. doi: 10.1073/pnas.1414622111. Epub 2014 Dec 1. PubMed PMID: 25453104; PubMed Central PMCID: PMC4273404. 6: Azofra LM, Alkorta I, Elguero J, Popelier PL. Conformational study of the open-chain and furanose structures of D-erythrose and D-threose. Carbohydr Res. 2012 Sep 1;358:96-105. doi: 10.1016/j.carres.2012.06.011. Epub 2012 Jun 27. PubMed PMID: 22841585. 7: Hernandez-García L, Quintero L, Sánchez M, Sartillo-Piscil F. Beneficial effect of internal hydrogen bonding interactions on the beta-fragmentation of primary alkoxyl radicals. Two-step conversion of D-xylo- and D-ribofuranoses into L-threose and D-erythrose, respectively. J Org Chem. 2007 Oct 26;72(22):8196-201. Epub 2007 Sep 27. PubMed PMID: 17900138. 8: Guo J, Frost JW. Biosynthesis of 1-deoxy-1-imino-D-erythrose 4-phosphate: a defining metabolite in the aminoshikimate pathway. J Am Chem Soc. 2002 Jan 30;124(4):528-9. PubMed PMID: 11804477. 9: Vogt JR, Lamm-Kolonko L, Renz P. Biosynthesis of vitamin B-12 in anaerobic bacteria. Experiments with Eubacterium limosum and D-erythrose 14C-labeled in different positions. Eur J Biochem. 1988 Jul 1;174(4):637-40. PubMed PMID: 2968906. 10: Hosomi S, Nakai N, Kogita J, Terada T, Mizoguchi T. Mechanism of enzymic isomerization and epimerization of D-erythrose 4-phosphate. Biochem J. 1986 Nov 1;239(3):739-43. PubMed PMID: 3827825; PubMed Central PMCID: PMC1147348. 11: Terada T, Mukae H, Ohashi K, Hosomi S, Mizoguchi T, Uehara K. Characterization of an enzyme which catalyzes isomerization and epimerization of D-erythrose 4-phosphate. Eur J Biochem. 1985 Apr 15;148(2):345-51. PubMed PMID: 3987693. 12: Terada T, Kohno T, Samejima T, Hosomi S, Mizoguchi T, Uehara K. Purification and properties of beef liver aldehyde reductase catalyzing the reduction of D-erythrose 4-phosphate. J Biochem. 1985 Jan;97(1):79-87. PubMed PMID: 3888976. 13: Privalle LS. Effects of D-erythrose on nitrogenase activity in whole filaments of Anabaena sp. strain 7120. J Bacteriol. 1984 Nov;160(2):794-6. PubMed PMID: 6238947; PubMed Central PMCID: PMC214809. 14: Ohashi K, Terada T, Kohno T, Hosomi S, Mizoguchi T, Uehara K. Enzymatic isomerization and epimerization of D-erythrose 4-phosphate and its quantitative analysis by gas chromatography/mass spectrometry. Eur J Biochem. 1984 Jul 16;142(2):347-53. PubMed PMID: 6547672. 15: Privalle LS, Burris RH. D-erythrose supports nitrogenase activity in isolated Anabaena sp. strain 7120 heterocysts. J Bacteriol. 1984 Feb;157(2):350-6. PubMed PMID: 6229527; PubMed Central PMCID: PMC215253. 16: Risley JM, Van Etten RL. Kinetics of oxygen exchange at the anomeric carbon atom of D-glucose and D-erythrose using the oxygen-18 isotope effect in carbon-13 nuclear magnetic resonance spectroscopy. Biochemistry. 1982 Dec 7;21(25):6360-5. PubMed PMID: 6217836. 17: Fujii S, Maruoka M. 2-amino-2-deoxy-D-erythrose in Agaricus bisporus. Biochim Biophys Acta. 1982 Aug 27;717(3):486-90. PubMed PMID: 6215066. 18: Le Maréchal P, Froussios C, Level M, Azerad R. Enzymic properties of phosphonic analogues of D-erythrose 4-phosphate. Biochem Biophys Res Commun. 1980 Feb 27;92(4):1097-103. PubMed PMID: 6102859. 19: Williams JF, Blackmore PF, Duke CC, MacLeod JK. Fact, uncertainty and speculation concerning the biochemistry of D-erythrose-4-phosphate and its metabolic roles. Int J Biochem. 1980;12(3):339-44. Review. PubMed PMID: 6998788. 20: Paoletti F, Williams JF, Horecker BL. An enyzmic method for the analysis of D-erythrose 4-phosphate. Anal Biochem. 1979 May;95(1):250-3. PubMed PMID: 158992. .