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Merck

860490P

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:
123-78-4
Molecular Weight:
299.49
MDL number:
MFCD00036751
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

Sphingosine (d18:1), Avanti Research™ - A Croda Brand

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

assay

>99% (TLC)

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

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).

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.

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

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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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)
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)
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)
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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