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860660P

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Sphingosine (d20:1)

Avanti Research™ - A Croda Brand 860660P, powder

Synonym(s):

D-erythro-sphingosine (C20 base)

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About This Item

Empirical Formula (Hill Notation):
C20H41NO2
CAS Number:
6918-49-6
Molecular Weight:
327.55
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860660P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860660P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

OC[C@@](N)([H])[C@]([H])(O)/C=C/CCCCCCCCCCCCCCC

InChI

1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(21)18-22/h16-17,19-20,22-23H,2-15,18,21H2,1H3/b17-16+/t19-,20+/m0/s1

InChI key

HTJSZHKGNMXZJN-YIVRLKKSSA-N

General description

Sphingosine (d20:1), also known as icosasphingosine, is a synthetic sphingosine with 20 carbon long chain bases (LCB). It is directly produced by the sphingolipid de novo synthesis pathway and not by hydrolysis of complex sphingolipids. In higher animals, it is one of the most abundant sphingoid bases of gangliosides.

Application

Sphingosine (d20:1) has been used as a reference substance in liquid chromatography/tandem mass spectrometry analysis to quantitatively analyze sphingolipids with C20- long chain bases in human central nervous tissue.

Biochem/physiol Actions

Sphingosine (d20:1) or C20-sphingosine acts as an intermediate in the synthesis of ceramides, which are vital components of mammalian epidermis. It may be involved in regulation of epidermal differentiation. C20 long chain bases-containing sphingolipids might exhibit detrimental effect on protein homeostasis and neural functions.

Packaging

5 mL Amber Glass Screw Cap Vial (860660P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

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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Lihong Zhao et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(42), 12962-12967 (2015-10-07)
Sphingolipids typically have an 18-carbon (C18) sphingoid long chain base (LCB) backbone. Although sphingolipids with LCBs of other chain lengths have been identified, the functional significance of these low-abundance sphingolipids is unknown. The LCB chain length is determined by serine
De novo sphingolipid biosynthesis: a necessary, but dangerous, pathway.
Alfred H Merrill
The Journal of biological chemistry, 277(29), 25843-25846 (2002-05-16)
P W Wertz et al.
Biochimica et biophysica acta, 1002(2), 213-217 (1989-04-03)
Sphingosines and phytosphingosines serve as intermediates in the synthesis of ceramides and glucosylceramides, which are prominent components of mammalian epidermis. In the present study, we have investigated the possibility that free sphingoid bases also may be present in epidermal tissue.
Thomas Kolter
ISRN biochemistry, 2012, 506160-506160 (2012-01-01)
Gangliosides are sialic acid-containing glycosphingolipids. They occur especially on the cellular surfaces of neuronal cells, where they form a complex pattern, but are also found in many other cell types. The paper provides a general overview on their structures, occurrence
Rajkumar Vutukuri et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 34(3), 3932-3942 (2020-01-17)
Sphingosine 1-phosphate (S1P) signaling influences numerous cell biological mechanisms such as differentiation, proliferation, survival, migration, and angiogenesis. Intriguingly, our current knowledge is based solely on the role of S1P with an 18-carbon long-chain base length, S1P d18:1. Depending on the
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