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860660P

Avanti

Sphingosine (d20:1)

Avanti Research™ - A Croda Brand 860660P, powder

Synonym(e):

D-erythro-sphingosine (C20 base)

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5 MG
€ 276,00

€ 276,00

Voraussichtliches Versanddatum16. April 2025

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5 MG
€ 276,00

About This Item

Empirische Formel (Hill-System):
C20H41NO2
CAS-Nummer:
6918-49-6
Molekulargewicht:
327.55
MDL-Nummer:
MFCD08703031
UNSPSC-Code:
12352211
NACRES:
NA.25

€ 276,00

Voraussichtliches Versanddatum16. April 2025

Bulk-Bestellung anfordern

Form

powder

Verpackung

pkg of 1 × 5 mg (860660P-5mg)

Hersteller/Markenname

Avanti Research™ - A Croda Brand 860660P

Lipid-Typ

sphingolipids

Versandbedingung

dry ice

Lagertemp.

−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

InChIKey

HTJSZHKGNMXZJN-YIVRLKKSSA-N

Allgemeine Beschreibung

Sphingosine (d20:1), also known as icosasphingosine, is a synthetic sphingosine with 20 carbon long chain bases (LCB).[1] It is directly produced by the sphingolipid de novo synthesis pathway and not by hydrolysis of complex sphingolipids.[2] In higher animals, it is one of the most abundant sphingoid bases of gangliosides.[3]

Anwendung

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.[2]

Biochem./physiol. Wirkung

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.[4] C20 long chain bases-containing sphingolipids might exhibit detrimental effect on protein homeostasis and neural functions.[5]

Verpackung

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

Rechtliche Hinweise

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

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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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