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Avanti

Sphingosine (d18:1)

Avanti Research - A Croda Brand

Synonym(s):

D-erythro-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C18H37NO2
CAS Number:
Molecular Weight:
299.49
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 10 mg (860490P-10mg)
pkg of 1 × 25 mg (860490P-25mg)
pkg of 1 × 500 mg (860490P-500mg)

manufacturer/tradename

Avanti Research - A Croda Brand

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1

InChI key

WWUZIQQURGPMPG-KRWOKUGFSA-N

General description

Sphingosine (d18:1) is a spingoid base present in plant and animals. It has 2-amino-1,3-diol functionality and its extraction from animal tissue is laborious. Sphingosine (d18:1) synthesis is performed by chirospecific method using D-galactose.

Application

Sphingosine (d18:1) has been used:
  • for sphingosine inhalations studies in mice to evaluate its therapeutic potential in respiratory epithelial cells
  • to investigate its effect on Pseudomonas aeruginosa strains
  • as a standard in liquid chromatography tandem mass spectrophotometry for the quantification of epidermal ceramides

Biochem/physiol Actions

Sphingosine (d18:1) is essential for physiological processes including cell differentiation, growth and survival. It activates the transient receptor potential cation channel subfamily member 3 (TRPM3).

Packaging

20 mL Clear Glass Screw Cap Vial (860490P-500mg)
5 mL Amber Glass Screw Cap Vial (860490P-10mg)
5 mL Amber Glass Screw Cap Vial (860490P-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Hazard Statements

Precautionary Statements

Hazard Classifications

Aquatic Chronic 4

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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The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog
Duclos Jr RI
Chemistry and Physics of Lipids, 111(2), 111-138 (2001)
Efficient Synthesis of d-erythro-Sphingosine and d-e rythro-Azidosphingosine from d-r ibo-Phytosphingosine via a Cyclic Sulfate Intermediate
Kim S, et al.
The Journal of Organic Chemistry, 71(22), 8661-8664 (2006)
Glucosylceramide critically contributes to the host defense of cystic fibrosis lungs
Kovacic B, et al.
Cellular Physiology and Biochemistry, 41(3), 1208-1218 (2017)
Sphingosine's role in epithelial host defense: A natural antimicrobial and novel therapeutic
Martin GE, et al.
Biochimie, 141, 91-96 (2017)
Transcription factor Ctip2 controls epidermal lipid metabolism and regulates expression of genes involved in sphingolipid biosynthesis during skin development
Wang Z, et al.
The Journal of Investigative Dermatology, 133(3), 668-676 (2013)

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