D-Mannuronic Acid | CAS#6906-37-2

MedKoo Cat#: 526111 | Name: D-Mannuronic Acid

Description:

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

D-Mannuronic Acid is a novel blocker of the TLR2 and TLR4 downstream signaling pathway, effectively inhibiting mRNA expression of MyD88 and p65, major subunit of nuclear factor-kappaB.

Chemical Structure

D-Mannuronic Acid

CAS#6906-37-2

Theoretical Analysis

MedKoo Cat#: 526111

Name: D-Mannuronic Acid

CAS#: 6906-37-2

Chemical Formula: C6H10O7

Exact Mass: 194.0427

Molecular Weight: 194.14

Elemental Analysis: C, 37.12; H, 5.19; O, 57.69

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

D-Mannuronic Acid

IUPAC/Chemical Name

(2S,3S,4S,5S)-3,4,5,6-Tetrahydroxyoxane-2-carboxylic acid

InChi Key

AEMOLEFTQBMNLQ-VANFPWTGSA-N

InChi Code

InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3-,4-,6?/m0/s1

SMILES Code

O=C([C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O)O

Appearance

Solid powder

Purity

>98% (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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 194.14 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: Vojdanian M, Ahmadi H, Jamshidi AR, Mahmoudi M, Gharibdoost F, Barati A, Mirshafiey A. The anti-migraine effects of M2000 (β-D-mannuronic acid) on a patient with rheumatoid arthritis; as a case report. Curr Clin Pharmacol. 2017 Jun 4. doi: 10.2174/1574884712666170605101845. [Epub ahead of print] PubMed PMID: 28578645. 2: Sanka I, Suyono EA, Alam P. The effects of diatom pore-size on the structures and extensibilities of single mucilage molecules. Carbohydr Res. 2017 May 26;448:35-42. doi: 10.1016/j.carres.2017.05.014. [Epub ahead of print] PubMed PMID: 28578200. 3: Barati A, Jamshidi AR, Ahmadi H, Aghazadeh Z, Mirshafiey A. Effects of β-d-mannuronic acid, as a novel non-steroidal anti-inflammatory medication within immunosuppressive properties, on IL17, RORγt, IL4 and GATA3 gene expressions in rheumatoid arthritis patients. Drug Des Devel Ther. 2017 Mar 30;11:1027-1033. doi: 10.2147/DDDT.S129419. eCollection 2017. PubMed PMID: 28408801; PubMed Central PMCID: PMC5384716. 4: Stewart MB, Myat DT, Kuiper M, Manning RJ, Gray SR, Orbell JD. A structural basis for the amphiphilic character of alginates - Implications for membrane fouling. Carbohydr Polym. 2017 May 15;164:162-169. doi: 10.1016/j.carbpol.2017.01.072. Epub 2017 Jan 22. PubMed PMID: 28325313. 5: Ahmadi H, Jamshidi AR, Mahmoudi M, Cuzzocrea S, Fattahi MJ, Barati A, Rehm BH, Matsou H, Mirshafiey A. The potent inhibitory effect of β-D-mannuronic acid (M2000) as a novel NSAID with immunosuppressive property on anti-cyclic citrullinated peptide antibodies, rheumatoid factor and anti-dsDNA antibodies in patients with rheumatoid arthritis. Curr Drug Discov Technol. 2017 Mar 21. doi: 10.2174/1570163814666170321113059. [Epub ahead of print] PubMed PMID: 28325148. 6: Jahromi SSM, Jamshidi MM, Farazmand A, Aghazadeh Z, Yousefi M, Mirshafiey A. Pharmacological effects of β-d-mannuronic acid (M2000) on miR-146a, IRAK1, TRAF6 and NF-κB gene expression, as target molecules in inflammatory reactions. Pharmacol Rep. 2017 Jun;69(3):479-484. doi: 10.1016/j.pharep.2017.01.021. Epub 2017 Jan 24. PubMed PMID: 28324845. 7: Hosseini F, Hassannia H, Mahdian-Shakib A, Jadidi-Niaragh F, Enderami SE, Fattahi M, Anissian A, Mirshafiey A, Kokhaei P. Targeting of crosstalk between tumor and tumor microenvironment by β-D mannuronic acid (M2000) in murine breast cancer model. Cancer Med. 2017 Mar;6(3):640-650. doi: 10.1002/cam4.1013. Epub 2017 Feb 17. PubMed PMID: 28211615; PubMed Central PMCID: PMC5345625. 8: Hosseini S, Abdollahi M, Azizi G, Fattahi MJ, Rastkari N, Zavareh FT, Aghazadeh Z, Mirshafiey A. Anti-aging effects of M2000 (β-D-mannuronic acid) as a novel immunosuppressive drug on the enzymatic and non-enzymatic oxidative stress parameters in an experimental model. J Basic Clin Physiol Pharmacol. 2017 Feb 16. pii: /j/jbcpp.ahead-of-print/jbcpp-2016-0092/jbcpp-2016-0092.xml. doi: 10.1515/jbcpp-2016-0092. [Epub ahead of print] PubMed PMID: 28207414. 9: Athari Nik Azm S, Vafa M, Sharifzadeh M, Safa M, Barati A, Mirshafiey A. Effects of M2000 (D-Mannuronic Acid) on Learning, Memory Retrieval, and Associated Determinants in a Rat Model of Alzheimer's Disease. Am J Alzheimers Dis Other Demen. 2017 Feb;32(1):12-21. doi: 10.1177/1533317516678086. Epub 2016 Dec 19. PubMed PMID: 28100077. 10: Qin HM, Miyakawa T, Inoue A, Nishiyama R, Nakamura A, Asano A, Sawano Y, Ojima T, Tanokura M. Structure and Polymannuronate Specificity of a Eukaryotic Member of Polysaccharide Lyase Family 14. J Biol Chem. 2017 Feb 10;292(6):2182-2190. doi: 10.1074/jbc.M116.749929. Epub 2016 Dec 23. PubMed PMID: 28011642; PubMed Central PMCID: PMC5313092. 11: Fawzy MA, Gomaa M, Hifney AF, Abdel-Gawad KM. Optimization of alginate alkaline extraction technology from Sargassum latifolium and its potential antioxidant and emulsifying properties. Carbohydr Polym. 2017 Feb 10;157:1903-1912. doi: 10.1016/j.carbpol.2016.11.077. Epub 2016 Nov 28. PubMed PMID: 27987910. 12: Aletaha S, Haddad L, Roozbehkia M, Bigdeli R, Asgary V, Mahmoudi M, Mirshafiey A. M2000 (β-D-Mannuronic Acid) as a Novel Antagonist for Blocking the TLR2 and TLR4 Downstream Signalling Pathway. Scand J Immunol. 2017 Feb;85(2):122-129. doi: 10.1111/sji.12519. PubMed PMID: 27943385. 13: Tabrizian N, Fard NA, Farazmand A, Eftekhari R, Zavareh FT, Mirshafiey A. The Biology of β-D-mannuronic acid (M2000) on Human Dendritic Cell Based on MicroRNA-155 and MicroRNA-221. Curr Drug Discov Technol. 2016 Nov 23. [Epub ahead of print] PubMed PMID: 27890012. 14: Fard NA, Tabrizian N, Mirzaei R, Motamed N, Zavareh FT, Mirshafiey A. The Safety Property of β-D-Mannuronic Acid (M2000) as a Novel Immunosuppressive Agent on Differentiation, Maturation and Function of Human Dendritic Cells. Curr Drug Discov Technol. 2016;13(3):164-169. PubMed PMID: 27335103. 15: Fischl R, Bertelsen K, Gaillard F, Coelho S, Michel G, Klinger M, Boyen C, Czjzek M, Hervé C. The cell-wall active mannuronan C5-epimerases in the model brown alga Ectocarpus: From gene context to recombinant protein. Glycobiology. 2016 Sep;26(9):973-983. Epub 2016 Mar 29. PubMed PMID: 27026155. 16: Khavari A, Löfroth JE, Bergenholtz J, Nydén M. On the percolation of alginate/calcium systems at low concentrations. Carbohydr Polym. 2016 Feb 10;137:480-7. doi: 10.1016/j.carbpol.2015.11.019. Epub 2015 Nov 10. PubMed PMID: 26686154. 17: Fattahi MJ, Abdollahi M, Agha Mohammadi A, Rastkari N, Khorasani R, Ahmadi H, Tofighi Zavareh F, Sedaghat R, Tabrizian N, Mirshafiey A. Preclinical assessment of β-d-mannuronic acid (M2000) as a non-steroidal anti-inflammatory drug. Immunopharmacol Immunotoxicol. 2015;37(6):535-40. doi: 10.3109/08923973.2015.1113296. PubMed PMID: 26584020. 18: Meng S, Winters H, Liu Y. Ultrafiltration behaviors of alginate blocks at various calcium concentrations. Water Res. 2015 Oct 15;83:248-57. doi: 10.1016/j.watres.2015.06.008. Epub 2015 Jun 9. PubMed PMID: 26164659. 19: Ertesvåg H. Alginate-modifying enzymes: biological roles and biotechnological uses. Front Microbiol. 2015 May 27;6:523. doi: 10.3389/fmicb.2015.00523. eCollection 2015. Review. PubMed PMID: 26074905; PubMed Central PMCID: PMC4444821. 20: Zhang Q, van Rijssel ER, Walvoort MT, Overkleeft HS, van der Marel GA, Codée JD. Acceptor reactivity in the total synthesis of alginate fragments containing α-L-guluronic acid and β-D-mannuronic acid. Angew Chem Int Ed Engl. 2015 Jun 22;54(26):7670-3. doi: 10.1002/anie.201502581. Epub 2015 May 8. PubMed PMID: 25960101.