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
• Article Data: 0

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

Different sources of media describe the Uses of 54827-14-4 differently. You can refer to the following data:
1. Monosialoganglioside GM3 can have anti-tumor effects by regulating cell apoptosis, angiogenesis. Monosialoganglioside GM3 can also regulate peripheral insulin receptor signaling and increases in GM3 in adipose tissue of obese humans may contribute to insulin resistance.
2. 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. It has also been used to determine ganglioside-binding profiles of methylotrophic yeast (Pichia pastoris) secreted cholera toxin B subunit (PpCTB) by enzyme-linked immunosorbent assay (ELISA).

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