Glucosamine free base
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MedKoo CAT#: 317975

CAS#: 3416-24-8 (free base)

Description: Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of the polysaccharides chitosan and chitin, which compose the exoskeletons of crustaceans and other arthropods, as well as the cell walls of fungi and many higher organisms. Glucosamine is commonly used as a treatment for osteoarthritis, although its acceptance as a medical therapy varies. Since glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage, supplemental glucosamine may help to rebuild cartilage and treat arthritis. (Source: https://en.wikipedia.org/wiki/Glucosamine).

Chemical Structure

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Glucosamine free base
CAS# 3416-24-8 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317975
Name: Glucosamine free base
CAS#: 3416-24-8 (free base)
Chemical Formula: C6H13NO5
Exact Mass: 179.08
Molecular Weight: 179.170
Elemental Analysis: C, 40.22; H, 7.31; N, 7.82; O, 44.65

Price and Availability

Size Price Availability Quantity
500mg USD 150 Ready to ship
1g USD 250 Ready to ship
2g USD 450 Ready to ship
5g USD 650 Ready to ship
10g USD 1150 Ready to ship
20g USD 2050 Ready to ship
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Related CAS #: 29031-19-4 (sulfate)   3416-24-8 (free base)   66-84-2 (HCl)  

Synonym: D-Glucosamine; Glucosamine; 2-Amino-2-Deoxy-D-Glucose; 2-Amino-2-Deoxy-D-Glucopyranose; Chitosamine

IUPAC/Chemical Name: (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol

InChi Key: MSWZFWKMSRAUBD-IVMDWMLBSA-N

InChi Code: InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1

SMILES Code: O[C@H]1[C@H](O)[C@@H](N)C(O)O[C@@H]1CO

Appearance: White to off-white 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 water

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: Oral glucosamine is a dietary supplement and is not a pharmaceutical drug. It is illegal in the US to market any dietary supplement as a treatment for any disease or condition. Glucosamine is marketed to support the structure and function of joints, and the marketing is targeted to people suffering from osteoarthritis. Commonly sold forms of glucosamine are glucosamine sulfate, glucosamine hydrochloride, and N-acetylglucosamine. Of the three commonly available forms of glucosamine, only glucosamine sulfate is given a "likely effective" rating for treating osteoarthritis. Glucosamine is often sold in combination with other supplements such as chondroitin sulfate and methylsulfonylmethane. Glucosamine, along with commonly used chondroitin, is not routinely prescribed to treat people who have symptomatic osteoarthritis of the knee, as there is insufficient evidence that this treatment is helpful. As is common with heavily promoted dietary supplements, the claimed benefits of glucosamine are based principally on clinical and laboratory studies. Clinical studies are divided, with some reporting relief from arthritic pain and stiffness, while higher quality studies report no benefit above placebo. There is no evidence to date that consumption of glucosamine by sport participants will prevent or limit joint damage after injury. In a randomized placebo-controlled trial, glucosamine supplementation had no additional effect on any rehabilitation outcome when given to athletes after anterior cruciate ligament (ACL) reconstruction.

Biological target: Glucosamine (2-amino-2-deoxy-D-glucose) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids.
In vitro activity: The effects of glucosamine on osteoblasts was examined. The potential underlying mechanisms were explored. The results showed that glucosamine had a biphasic effect on the viability of hFOB1.19 osteoblasts. At low concentrations (<0.6 mM), glucosamine induced hFOB1.19 cell proliferation, whereas at high concentrations (>0.8 mM) it induced apoptosis. The autophagy inhibitor 3-methyladenine (3-MA) was used to verify that glucosamine modulated hFOB1.19 cell viability via autophagy. The induction of apoptosis by high concentrations of glucosamine was significantly exacerbated by 3-MA, whereas the promotion of cell proliferation by low concentrations of glucosamine was significantly suppressed by 3-MA. Autophagy was examined by western blot detection of autophagy-related proteins including LC3, Beclin-1, and SQSTM1/p62 and by immunofluorescence analysis of autophagosomes. Glucosamine activated autophagy in a time- and concentration-dependent manner. Investigation of the underlying mechanism showed that glucosamine inhibited the phosphorylation of m-TOR in a concentration-dependent manner within 48 h. These results demonstrated that glucosamine promoted hFOB1.19 cell proliferation and increased autophagy by inhibiting the m-TOR pathway, suggesting its potential as a therapeutic agent for osteoporosis. Reference: Biomed Pharmacother. 2018 Mar;99:271-277. https://linkinghub.elsevier.com/retrieve/pii/S0753-3322(17)36142-5
In vivo activity: The aim of the current study was to investigate the effects of glucosamine (GlcN) on septic lethality and sepsis-induced inflammation using animal models of mice and zebrafish. GlcN pretreatment improved survival in the cecal ligation and puncture (CLP)-induced sepsis mouse model and attenuated lipopolysaccharide (LPS)-induced septic lung injury and systemic inflammation. GlcN suppressed LPS-induced M1-specific but not M2-specific gene expression. Furthermore, increased expressions of inflammatory genes in visceral tissue of LPS-injected zebrafish were suppressed by GlcN. GlcN suppressed LPS-induced activation of mitogen-activated protein kinase (MAPK) and NF-κB in lung tissue. LPS triggered a reduction in O-GlcNAc levels in nucleocytoplasmic proteins of lung, liver, and spleen after 1 day, which returned to normal levels at day 3. GlcN inhibited LPS-induced O-GlcNAc down-regulation in mouse lung and visceral tissue of zebrafish. Furthermore, the O-GlcNAcase (OGA) level was increased by LPS, which were suppressed by GlcN in mouse and zebrafish. OGA inhibitors suppressed LPS-induced expression of inflammatory genes in RAW264.7 cells and the visceral tissue of zebrafish. Stable knockdown of Oga via short hairpin RNA led to increased inducible nitric oxide synthase (iNOS) expression in response to LPS with or without GlcN in RAW264.7 cells. Overall, our results demonstrate a protective effect of GlcN on sepsis potentially through modulation of O-GlcNAcylation of nucleocytoplasmic proteins. Reference: J Biol Chem. 2019 Jan 11;294(2):608-622. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30455348/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 23.0 128.37
Water 36.0 200.93

Preparing Stock Solutions

The following data is based on the product molecular weight 179.17 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:
In vitro protocol: 1. Lv C, Wang L, Zhu X, Lin W, Chen X, Huang Z, Huang L, Yang S. Glucosamine promotes osteoblast proliferation by modulating autophagy via the mammalian target of rapamycin pathway. Biomed Pharmacother. 2018 Mar;99:271-277. doi: 10.1016/j.biopha.2018.01.066. PMID: 29334671. 2. Lei X, Ma N, Liang Y, Liu J, Zhang P, Han Y, Chen W, Du L, Qu B. Glucosamine protects against radiation-induced lung injury via inhibition of epithelial-mesenchymal transition. J Cell Mol Med. 2020 Sep;24(18):11018-11023. doi: 10.1111/jcmm.15662. Epub 2020 Jul 22. PMID: 32700471; PMCID: PMC7521322.
In vivo protocol: 1. Hwang JS, Kim KH, Park J, Kim SM, Cho H, Lee Y, Han IO. Glucosamine improves survival in a mouse model of sepsis and attenuates sepsis-induced lung injury and inflammation. J Biol Chem. 2019 Jan 11;294(2):608-622. doi: 10.1074/jbc.RA118.004638. Epub 2018 Nov 19. PMID: 30455348; PMCID: PMC6333887. 2. Lei X, Ma N, Liang Y, Liu J, Zhang P, Han Y, Chen W, Du L, Qu B. Glucosamine protects against radiation-induced lung injury via inhibition of epithelial-mesenchymal transition. J Cell Mol Med. 2020 Sep;24(18):11018-11023. doi: 10.1111/jcmm.15662. Epub 2020 Jul 22. PMID: 32700471; PMCID: PMC7521322.

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1: Peluso R, Caso F, Costa L, Sorbo D, Carraturo N, Di Minno MN, Carraturo F, Oriente A, Balestrieri U, Minicucci A, Del Puente A, Scarpa R. Mud-bath therapy and oral glucosamine sulfate in patients with knee osteoarthritis: a randomized, controlled, crossover study. Clin Exp Rheumatol. 2016 Apr 6. [Epub ahead of print] PubMed PMID: 27050908.

2: Terencio MC, Ferrándiz ML, Carceller MC, Ruhí R, Dalmau P, Vergés J, Montell E, Torrent A, Alcaraz MJ. Chondroprotective effects of the combination chondroitin sulfate-glucosamine in a model of osteoarthritis induced by anterior cruciate ligament transection in ovariectomised rats. Biomed Pharmacother. 2016 Apr;79:120-8. doi: 10.1016/j.biopha.2016.02.005. Epub 2016 Feb 18. PubMed PMID: 27044820.

3: Hrynets Y, Bhattacherjee A, Ndagijimana M, Hincapie Martinez DJ, Betti M. Iron (Fe(2+))-Catalyzed Glucosamine Browning at 50 °C: Identification and Quantification of Major Flavor Compounds for Antibacterial Activity. J Agric Food Chem. 2016 Apr 27;64(16):3266-75. doi: 10.1021/acs.jafc.6b00761. Epub 2016 Apr 11. PubMed PMID: 27043007.

4: Furuike T, Chaochai T, Okubo T, Mori T, Tamura H. Fabrication of nonwoven fabrics consisting of gelatin nanofibers cross-linked by glutaraldehyde or N-acetyl-d-glucosamine by aqueous method. Int J Biol Macromol. 2016 Mar 25. pii: S0141-8130(16)30277-X. doi: 10.1016/j.ijbiomac.2016.03.053. [Epub ahead of print] PubMed PMID: 27020944.

5: Kim C, Shores L, Guo Q, Aly A, Jeon OH, Kim do H, Bernstein N, Bhattacharya R, Chae JJ, Yarema KJ, Elisseeff JH. Electrospun Microfiber Scaffolds with Anti-Inflammatory Tributanoylated N-Acetyl-d-Glucosamine Promote Cartilage Regeneration. Tissue Eng Part A. 2016 Apr;22(7-8):689-97. doi: 10.1089/ten.TEA.2015.0469. PubMed PMID: 27019285.

6: Bennett AM, Shippy DC, Eakley N, Okwumabua O, Fadl AA. Functional characterization of glucosamine-6-phosphate synthase (GlmS) in Salmonella enterica serovar Enteritidis. Arch Microbiol. 2016 Mar 26. [Epub ahead of print] PubMed PMID: 27017337.

7: Forman A, Auzanneau FI. Orthoesters formation leading to mismatched Helferich glycosylations at O-3 of N-trichloroacetylated glucosamine residues. Carbohydr Res. 2016 Apr 29;425:10-21. doi: 10.1016/j.carres.2016.02.012. Epub 2016 Mar 10. PubMed PMID: 27015141.

8: Dalirfardouei R, Karimi G, Jamialahmadi K. Molecular mechanisms and biomedical applications of glucosamine as a potential multifunctional therapeutic agent. Life Sci. 2016 Mar 16. pii: S0024-3205(16)30179-5. doi: 10.1016/j.lfs.2016.03.028. [Epub ahead of print] Review. PubMed PMID: 27012765.

9: Álvarez-Añorve LI, Gaugué I, Link H, Marcos-Viquez J, Díaz-Jiménez DM, Zonszein S, Bustos-Jaimes I, Schmitz-Afonso I, Calcagno ML, Plumbridge J. Allosteric activation of E. coli glucosamine-6-phosphate deaminase (NagB) in vivo justified by intracellular amino sugar metabolite concentrations. J Bacteriol. 2016 Mar 21. pii: JB.00870-15. [Epub ahead of print] PubMed PMID: 27002132.

10: Lin H, Zeng J, Xie R, Schulz MJ, Tedesco R, Qu J, Erhard KF, Mack JF, Raha K, Rendina AR, Szewczuk LM, Kratz PM, Jurewicz AJ, Cecconie T, Martens S, McDevitt PJ, Martin JD, Chen SB, Jiang Y, Nickels L, Schwartz BJ, Smallwood A, Zhao B, Campobasso N, Qian Y, Briand J, Rominger CM, Oleykowski C, Hardwicke MA, Luengo JI. Discovery of a Novel 2,6-Disubstituted Glucosamine Series of Potent and Selective Hexokinase 2 Inhibitors. ACS Med Chem Lett. 2015 Dec 28;7(3):217-22. doi: 10.1021/acsmedchemlett.5b00214. eCollection 2016 Mar 10. PubMed PMID: 26985301; PubMed Central PMCID: PMC4789681.