(2S,3S,4R)-2-aminooctadecane-1,3,4-triol hydrochloride

• ChemBase ID: 133606
• Molecular Formular: C18H40ClNO3
• Molecular Mass: 353.9681
• Monoisotopic Mass: 353.26967183
• SMILES: CCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)N)O)O.Cl
• Canonical SMILES: CCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)N)O)O.Cl
• InChI: InChI=1S/C18H39NO3.ClH/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20;/h16-18,20-22H,2-15,19H2,1H3;1H/t16-,17+,18-;/m0./s1
• InChIKey: GDKAAHDFPOWGQE-RXQQAGQTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R)-2-aminooctadecane-1,3,4-triol hydrochloride
• IUPAC Traditional name: phytosphingosine hydrochloride
• Synonyms: 4-Hydroxysphinganine; D-Ribo-1,3,4-trihydroxy-2-aminooctadecane; D-Ribo-2-aminooctadecane-1,3,4-triol; PHS; Phytosphingosine hydrochloride

Database IDs

• CAS Number: 554-62-1
• MDL Number: MFCD06804643
• PubChem SID: 162227883; 24898363
• PubChem CID: 9928513

CALCULATED PROPERTIES

• Acid pKa: 13.447719
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 0.81708914
• LogD (pH = 7.4): 2.1886828
• Log P: 3.6976907
• Molar Refractivity: 92.2909 cm^3
• Polarizability: 37.26658 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 1
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~97%
• Biological Source: from Saccharomyces cerevisiae

DETAILS

Sigma Aldrich - P2795

Biochem/physiol Actions
Phytosphingosine is a long chain sphingoid base that occurs broadly in yeast, plants and animals including mammals. In yeast it is involved in mediating the heat stress response, perhaps through activation of the AGC-type protein kinases, Pkh1, Pkh2, Ypk1, Ypk2, and Sch9. It is proapoptotic in human cancer cell lines. PHS induces ΔΨm and release of cytochrome c from mitochondria either directly or through activation of p38 MAPK pathway. This leads to activation of caspase 9 followed by activation of caspase 3 and programmed cell death.