54827-14-4

Basic information

• Product Name: MONOSIALOGANGLIOSIDE GM3
• Synonyms: Monosialoganglioside GM3, Bovine (NH4+ salt);Monosialoganglioside GM3 (bovine)(aMMoniuM salt);Ganglioside M3;Hematoside;Sialosyllactosylceramide;(2S,4S,5R)-2-((2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-4,5-dihydroxy-6-((2S,3R,E)-3-hydroxy-2-octadecanamidooctadec-4-enyloxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-5-ethanamido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid;Ganglioside GM3 (d18:1/18:0);(2S,4S,5R)-2-((2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-4,5-dihydroxy-6-((2S,3R,E)-3-hydroxy-2-icosanamidooctadec-4-enyloxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-5-ethanamido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
• CAS NO: 54827-14-4
• Molecular Formula: C64H118N2O21.H3N
• Molecular Weight: 1268.66
• Product Categories: Acidic glycosphingolipids;GangliosidesGlycan Component Classes;GangliosidesSphingolipids;Cell Signaling and Neuroscience;Gangliosides;Glycosphingolipids;Lipids in Cell Signaling
• Mol File: 54827-14-4.mol

Chemical Properties

• Boiling Point: 1257.6 °C at 760 mmHg
• Flash Point: 714.4 °C
• Appearance: /lyophilized powder
• Density: 1.27 g/cm³
• Refractive Index: 1.573
• Storage Temp.: −20°C
• Solubility: chloroform/methanol/water (9.5:9.5:1): 20mg/mLclear, colorless t
• CAS DataBase Reference: MONOSIALOGANGLIOSIDE GM3(CAS DataBase Reference)
• NIST Chemistry Reference: MONOSIALOGANGLIOSIDE GM3(54827-14-4)
• EPA Substance Registry System: MONOSIALOGANGLIOSIDE GM3(54827-14-4)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 54827-14-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Monosialoganglioside GM3 is used as an anti-tumor agent for its ability to regulate cell apoptosis and angiogenesis, which are critical processes in tumor growth and progression. It has shown potential in targeting and inhibiting the growth of various types of cancer cells.
Additionally, Monosialoganglioside GM3 is used as a regulator of peripheral insulin receptor signaling. The increase in GM3 levels in adipose tissue of obese humans may contribute to insulin resistance, making it a potential therapeutic target for treating obesity-related insulin resistance and type 2 diabetes.
Used in Research and Diagnostic Applications:
In the field of research and diagnostics, Monosialoganglioside GM3 from canine blood has been used as a reference standard in high-performance thin-layer chromatography (HPTLC) to analyze ganglioside signatures of prostate cancer (CaP) cells. This helps in the identification and characterization of specific gangliosides associated with cancer cells, aiding in the development of targeted therapies and diagnostic tools.
Furthermore, Monosialoganglioside GM3 has been used to determine ganglioside-binding profiles of methylotrophic yeast (Pichia pastoris) secreted cholera toxin B subunit (PpCTB) by enzyme-linked immunosorbent assay (ELISA). This application is crucial for understanding the interaction between gangliosides and various toxins, which can provide insights into the development of vaccines and therapeutic agents against toxin-mediated diseases.

Biochem/physiol Actions

Monosialoganglioside GM3 has a potential role in cancer development and progression. Increased expression of GM3 has been observed in various types of cancer. Hence, it is used as a tumor-associated carbohydrate antigen during cancer vaccine development.

InChI:InChI=1/C53H96N2O21/c1-4-6-8-10-12-14-15-16-17-19-20-22-24-26-35(60)34(55-40(63)27-25-23-21-18-13-11-9-7-5-2)32-71-50-45(67)44(66)47(39(31-58)73-50)74-51-46(68)49(43(65)38(30-57)72-51)76-53(52(69)70)28-36(61)41(54-33(3)59)48(75-53)42(64)37(62)29-56/h24,26,34-39,41-51,56-58,60-62,64-68H,4-23,25,27-32H2,1-3H3,(H,54,59)(H,55,63)(H,69,70)/b26-24+/t34-,35+,36-,37+,38+,39+,41+,42+,43-,44+,45?,46+,47+,48?,49-,50+,51-,53-/m0/s1