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P2795

Sigma-Aldrich

Phytosphingosine hydrochloride

greener alternative

Synonym(s):

4-Hydroxysphinganine, D-Ribo-1,3,4-trihydroxy-2-aminooctadecane, D-Ribo-2-aminooctadecane-1,3,4-triol, PHS

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About This Item

Empirical Formula (Hill Notation):
C18H39NO3 · HCl
CAS Number:
554-62-1
Molecular Weight:
353.97
MDL number:
MFCD06804643
UNSPSC Code:
12352211
PubChem Substance ID:
24898363
NACRES:
NA.25

form

powder

Quality Level

200

greener alternative product score

old score: 19
new score: 9
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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

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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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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