(2R,3R,4S,5R,6R)-2-{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 131453
• Molecular Formular: C24H47NO7
• Molecular Mass: 461.63248
• Monoisotopic Mass: 461.33525285
• SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)N)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)N)O
• InChI: InChI=1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18-,19+,20+,21-,22-,23+,24+/m0/s1
• InChIKey: HHJTWTPUPVQKNA-PIIMIWFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6R)-2-{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: psychosine
• Synonyms: 1-β-D-Galactosylsphingosine; Psychosine from bovine brain; (2S,3R,4E)-2-Amino-3-hydroxy-4-octadecen-1-yl α-D-Galactopyranoside; α-Galactosyl erythro-Sphingosine

Database IDs

• CAS Number: 2238-90-6
• MDL Number: MFCD00057505
• PubChem SID: 24899021; 162225731
• PubChem CID: 5280458

CALCULATED PROPERTIES

• Acid pKa: 12.206499
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -0.13794628
• LogD (pH = 7.4): 1.0860742
• Log P: 2.7957444
• Molar Refractivity: 124.3053 cm^3
• Polarizability: 49.999756 Å^3
• Polar Surface Area: 145.63 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: lyophilized powder; White to off-white solid
• Melting Point: 205-208°C

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - P9256

Biochem/physiol Actions
Glycolipid precursor of cerebrosides
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P9256.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - G185075

Galactosylceramides play an important roles in promoting the regulation of nerve cells, regulating protein kinase C activities and modulating the function of the hormone receptor. It has shown to have significant immunostimulatory and anti-umor activity