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Merck
CN

P2795

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
NACRES:
NA.25
PubChem Substance ID:
24898363
UNSPSC Code:
12352211
MDL number:
MFCD06804643

Key Documents

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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

SMILES string

Cl.CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO

InChI key

GDKAAHDFPOWGQE-RXQQAGQTSA-N

form

powder

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
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sustainability

Greener Alternative Product

greener alternative category

, Re-engineered

lipid type

sphingolipids

storage temp.

−20°C

Quality Level

200

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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

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000492356
0000492356
0000482186
0000482186
0000462986

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Hyeseung Lee et al.
Molecular microbiology, 84(1), 130-146 (2012-02-22)
This study shows the importance of PDK1, TOR and PKC signalling pathways to the basal tolerance of Cryptococcus neoformans towards fluconazole, the widely used drug for treatment of cryptococcosis. Mutations in genes integral to these pathway resulted in hypersensitivity to
Marie-Thérèse El-Daher et al.
The EMBO journal, 34(17), 2255-2271 (2015-07-15)
Cleavage of mutant huntingtin (HTT) is an essential process in Huntington's disease (HD), an inherited neurodegenerative disorder. Cleavage generates N-ter fragments that contain the polyQ stretch and whose nuclear toxicity is well established. However, the functional defects induced by cleavage
Ineke Spruijt et al.
PloS one, 14(7), e0219252-e0219252 (2019-07-02)
To reach pre-elimination levels of tuberculosis (TB) incidence in the Netherlands, prevention of TB among immigrants through diagnosis and treatment of latent TB infection (LTBI) is needed. We studied the feasibility of a LTBI screening and treatment program among newly
Karin Thevissen et al.
FEMS microbiology letters, 303(2), 163-168 (2009-12-25)
We demonstrated that a yeast deletion mutant in IPT1 and SKN1, encoding proteins involved in the biosynthesis of mannosyldiinositolphosphoryl ceramides, is characterized by increased autophagy and DNA fragmentation upon nitrogen (N) starvation as compared with the single deletion mutants or
Body Size Indicators and Risk of Gallbladder Cancer: Pooled Analysis of Individual-Level Data from 19 Prospective Cohort Studies.
Peter T Campbell et al.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology, 26(4), 597-606 (2017-03-21)
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