(2S,3R)-2-aminooctadecane-1,3-diol

• ChemBase ID: 132944
• Molecular Formular: C18H39NO2
• Molecular Mass: 301.50776
• Monoisotopic Mass: 301.29807949
• SMILES: CCCCCCCCCCCCCCC[C@H]([C@H](CO)N)O
• Canonical SMILES: CCCCCCCCCCCCCCC[C@H]([C@H](CO)N)O
• InChI: InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1
• InChIKey: OTKJDMGTUTTYMP-ZWKOTPCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-aminooctadecane-1,3-diol
• IUPAC Traditional name: sphinganine
• Synonyms: Sphinganine; D-erythro-Dihydrosphingosine; (2S,3R)-2-Amino-1,3-octadecanediol; C18-Dihydrosphingosine; D-erythro-1,3-Dihydroxy-2-aminooctadecane; D-erythro-2-Amino-1,3-octadecanediol; Dihydrosphingosine; Octadecasphinganine; SPC 102860; erythro-Sphinganine; D-erythro-C18-Dihydro-D-sphingosine

Database IDs

• CAS Number: 764-22-7
• MDL Number: MFCD07371371
• PubChem SID: 24893744; 162227221
• PubChem CID: 91486

CALCULATED PROPERTIES

• Acid pKa: 14.419876
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.8097895
• LogD (pH = 7.4): 2.9092555
• Log P: 4.7725945
• Molar Refractivity: 90.9294 cm^3
• Polarizability: 36.661594 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO: soluble25 mg/mL (warm); ethanol: soluble25 mg/mL (warm); Ethyl Acetate; Methanol
• Apperance: white; White Powder
• Melting Point: 70-72°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%

DETAILS

Sigma Aldrich - D3314

Biochem/physiol Actions
Biosynthetic precursor to sphingosine; inhibits protein kinase C.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D3314.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - D449400

Biosynthetic precursor of Sphingosine. Inhibits protein kinase C.

REFERENCES

• Merrill, A.H. Jr., et al.: Biochemistry, 28, 3138 (1989)