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860488P

Avanti

Safingol

Avanti Research™ - A Croda Brand 860488P, powder

Synonym(s):

L-threo-dihydrosphingosine (d18:0) z

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About This Item

Empirical Formula (Hill Notation):
C18H39NO2
CAS Number:
15639-50-6
Molecular Weight:
301.51
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860488P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860488P

lipid type

sphingolipids
bioactive lipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCC[C@@](O)([H])[C@@]([H])(N)CO

InChI

1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3

InChI key

OTKJDMGTUTTYMP-UHFFFAOYSA-N

General description

Safingol is a synthetic L-threo-stereoisomer of endogenous (D-erythro-) sphinganine. It acts as an inhibitor of protein kinase C and sphingosine kinase in vitro. Safingol is involved in ceramide generation and induction of apoptosis. It is known to stimulate antitumor activity of cisplatin.

Application

Safingol has been used as a substituent of dihydrosphingosine (dhSph) to increase the cytotoxic response in N-(4-hydroxyphenyl)retinamide (4-HPR)-resistant cells.

Packaging

5 mL Amber Glass Screw Cap Vial (860488P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A phase I clinical study of safingol followed by cisplatin: promising activity in refractory adrenocortical cancer with novel pharmacology
Carvajal RD, et al.
Journal of Clinical Oncology, 24(18), 13044-13044 (2006)
Safingol (L-threo-sphinganine) induces autophagy in solid tumor cells through inhibition of PKC and the PI3-kinase pathway
Coward J, et al.
Autophagy, 5(2), 184-193 (2009)
Andrej Kováčik et al.
Langmuir : the ACS journal of surfaces and colloids, 34(1), 521-529 (2017-12-13)
Ceramides (Cer) are key components of the skin permeability barrier. Sphingosine-based CerNS and dihydrosphingosine-based CerNdS (dihydroCer) have two chiral centers; however, the importance of the correct stereochemistry in the skin barrier Cer is unknown. We investigated the role of the
Evaluation of bioactive sphingolipids in 4-HPR-resistant leukemia cells
Apraiz A, et al.
BMC Cancer, 11(1), 477-477 (2011)

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