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P4194

Sigma-Aldrich

DL-threo-1-Phenyl-2-palmitoylamino-3-morpholino-1-propanol

98%

Synonym(s):

(±)-PPMP

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About This Item

Empirical Formula (Hill Notation):
C29H50N2O3 · HCl
CAS Number:
149022-18-4
Molecular Weight:
511.18
MDL number:
MFCD00211157
UNSPSC Code:
12352211
PubChem Substance ID:
24898512
NACRES:
NA.25

Assay

98%

form

powder

lipid type

phosphoglycerides

storage temp.

2-8°C

SMILES string

CCCCCCCCCCCCCCCC(=O)N[C@H](CN1CCOCC1)[C@H](O)c2ccccc2

InChI

1S/C29H50N2O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-28(32)30-27(25-31-21-23-34-24-22-31)29(33)26-18-15-14-16-19-26/h14-16,18-19,27,29,33H,2-13,17,20-25H2,1H3,(H,30,32)/t27-,29-/m1/s1

InChI key

OFBANDBMHLEMFA-XRKRLSELSA-N

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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D Johansson et al.
British journal of cancer, 102(2), 383-391 (2009-12-17)
A major problem with cisplatin treatment is the development of acquired-drug resistance of the tumour cells. Verotoxin-1 (VT-1) exerts its cytotoxicity by targeting the membrane glycolipid globotriasosylceramide (Gb3), a molecule associated with drug resistance. Cisplatin- and VT-1-induced apoptosis involves mitogen-activated
A Abe et al.
Journal of biochemistry, 111(2), 191-196 (1992-02-01)
An inhibitor of glucosylceramide (GlcCer) synthase, 1-phenyl-2-decanoylamino-3-morpholino-1-propanol (PDMP), has been reported to deplete cells and mice of their glucosphingolipids. This inhibitor has proved useful for the elucidation of the many functions of this lipid family [reviewed by Radin, N.S. &
Takuya Honda et al.
Biochimica et biophysica acta. Molecular and cell biology of lipids, 1866(1), 158817-158817 (2020-09-28)
Sphingolipids represent a family of cellular lipid-molecules that regulate physiological and pathophysiological processes. Glucosylceramide (GlcCer), the simplest glycosphingolipid (GSL), is synthesized from ceramide and UDP-glucose by GlcCer synthase (GCS). Both GlcCer (and resulting GSLs) and ceramide regulate various cellular functions
Tomasz B Owczarek et al.
PloS one, 8(12), e84191-e84191 (2014-01-07)
It was recently proposed that UDP-galactose:ceramide galactosyltransferase (UGT8), enzyme responsible for synthesis of galactosylceramide (GalCer), is a significant index of tumor aggressiveness and a potential marker for the prognostic evaluation of lung metastases in breast cancer. To further reveal the
Dorothee Gramatzki et al.
PloS one, 8(5), e63527-e63527 (2013-05-15)
Resistance to genotoxic therapy is a characteristic feature of glioma cells. Acid sphingomyelinase (ASM) hydrolyzes sphingomyelin to ceramide and glucosylceramide synthase (GCS) catalyzes ceramide metabolism. Increased ceramide levels have been suggested to enhance chemotherapy-induced death of cancer cells. Microarray and
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