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860674P

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Sphinganine (d20:0)

Avanti Research™ - A Croda Brand 860674P, powder

Synonym(s):

D-erythro-sphinganine (C20 base)

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About This Item

Empirical Formula (Hill Notation):
C20H43NO2
CAS Number:
24006-62-0
Molecular Weight:
329.56
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860674P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860674P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

OC[C@@](N)([H])[C@]([H])(O)CCCCCCCCCCCCCCCCC

InChI

1S/C20H43NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(21)18-22/h19-20,22-23H,2-18,21H2,1H3/t19-,20+/m0/s1

InChI key

UFMHYBVQZSPWSS-VQTJNVASSA-N

General description

Sphinganine (d20:0), also known as C20 dihydrosphingosine or icosasphinganine, is a C20 analog of sphinganine. Sphinganine is a derivative of sphingosine. It is formed in endoplasmic reticulum, by decarboxylating condensation of palmitoyl-CoA and serine.

Application

Sphinganine (d20:0) has been used as a standard in gas chromatography-mass spectrometry (GC-MS) for the quantitative analysis of plant sphingolipid long-chain bases.

Biochem/physiol Actions

Sphinganine (d20:0) is implicated in yeast heat stress adaptation. Sphinganine inhibits protein kinase C in intact human neutrophils. It might act as a biomarker for the diagnosis of sphingolipidoses. It inhibits cholesterol transport in Niemann-Pick Type C (NPC) disease.

Packaging

5 mL Amber Glass Screw Cap Vial (860674P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

Certificates of Analysis (COA)

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G M Jenkins et al.
The Journal of biological chemistry, 272(51), 32566-32572 (1998-01-24)
A role for sphingolipids in the yeast heat stress response has been suggested by the isolation of suppressors of mutants lacking these lipids, which are unable to grow at elevated temperatures. The current study examines the possible role of sphingolipids
Lipids
Basic neurochemistry: principles of molecular, cellular, and medical neurobiology (2011)
Graham Brogden et al.
Biomolecules, 9(9) (2019-09-11)
Sphingolipids are an important group of lipids that play crucial roles in living cells, facilitating cell recognition, signal transduction and endocytosis. The concentration of sphingosine and some of its derivatives like sphinganine may serve as a biomarker for the diagnosis
C F Roff et al.
Developmental neuroscience, 13(4-5), 315-319 (1991-01-01)
Niemann-Pick Type C (NPC) disease is a cholesterol lipidosis resulting from defective postlysosomal cholesterol transport. In normal cells this segment of cholesterol trafficking is inhibited by treatment with either U18666A or imipramine. Other compounds are also capable of blocking postlysosomal
D Pittet et al.
The Journal of biological chemistry, 262(21), 10072-10076 (1987-07-25)
Sphinganine has been proposed to be a specific inhibitor of protein kinase C. In the present study we have evaluated whether sphinganine is a convenient tool to probe for the role of protein kinase C in neutrophil function. Human neutrophils
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