P2795

Phytosphingosine hydrochloride

• Synonym(s): 4-Hydroxysphinganine, D-Ribo-1,3,4-trihydroxy-2-aminooctadecane, D-Ribo-2-aminooctadecane-1,3,4-triol, PHS
• Empirical Formula (Hill Notation): C₁₈H₃₉NO₃ · HCl
• CAS Number: 554-62-1
• Molecular Weight: 353.97
• NACRES: NA.25
• PubChem Substance ID: 24898363
• UNSPSC Code: 12352211
• MDL number: MFCD06804643

Properties

• form: powder
• Quality Segment: 200
• greener alternative product score: old score: 19; new score: 9; Find out more about DOZN™ Scoring
• greener alternative product characteristics: Less Hazardous Chemical Syntheses; Safer Solvents and Auxiliaries; Use of Renewable Feedstocks; Learn more about the Principles of Green Chemistry.
• sustainability: Greener Alternative Product
• greener alternative category: , Re-engineered
• lipid type: sphingolipids
• storage temp.: −20°C
• SMILES string: Cl.CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO
• 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
• InChI key: GDKAAHDFPOWGQE-RXQQAGQTSA-N

Description

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 ΔΨ_m 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.

Safety Information

• Storage Class: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): Eyeshields, Gloves, type N95 (US)