ChemicalBook > CAS DataBase List > D-ERYTHRO-SPHINGOSINE

D-ERYTHRO-SPHINGOSINE

Product Name
D-ERYTHRO-SPHINGOSINE
CAS No.
123-78-4
Chemical Name
D-ERYTHRO-SPHINGOSINE
Synonyms
SPHINGOSINE;D-SPHINGOSINE;Sphingosine (d18:1);CEREBROSIDE;Sphingenine;SPHINGOSINE, D-ERYTHRO;(2S,3R,E)-2-aMinooctadec-4-ene-1,3-diol;BRAIN, BOVINE;4-SPHINGENINE;D-Sphingenine
CBNumber
CB1262764
Molecular Formula
C18H37NO2
Formula Weight
299.49
MOL File
123-78-4.mol
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D-ERYTHRO-SPHINGOSINE Property

Melting point:
74.2-78.1 °C
Boiling point:
440.8°C (rough estimate)
Density 
0.9758 (rough estimate)
refractive index 
1.5000 (estimate)
storage temp. 
-20°C
solubility 
chloroform: 20 mg/mL, clear, colorless to very faintly yellow
form 
Powder or Waxy Solid
pka
11.80±0.45(Predicted)
color 
White to cream
Merck 
14,8747
BRN 
1727294
Stability:
Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
InChIKey
WWUZIQQURGPMPG-KRWOKUGFSA-N
CAS DataBase Reference
123-78-4
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
F 
1-8-10
HS Code 
29221985
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
44066
Product name
D-Sphingosine
Purity
≥98.0% (TLC)
Packaging
50mg
Price
$513
Updated
2023/06/20
Sigma-Aldrich
Product number
44066
Product name
D-Sphingosine
Purity
≥98.0% (TLC)
Packaging
250mg
Price
$1870
Updated
2023/06/20
TCI Chemical
Product number
S0874
Product name
D-Sphingosine
Purity
>96.0%(GC)
Packaging
25mg
Price
$170
Updated
2024/03/01
Alfa Aesar
Product number
J63584
Product name
D-erythro-Sphingosine, 99+%
Packaging
10mg
Price
$98.65
Updated
2024/03/01
Alfa Aesar
Product number
J63584
Product name
D-erythro-Sphingosine, 99+%
Packaging
25mg
Price
$189.65
Updated
2024/03/01
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D-ERYTHRO-SPHINGOSINE Chemical Properties,Usage,Production

Description

Sphingosine (123-78-4) is an inhibitor of protein kinase C (IC50 = 1-3 μM).1 It is abundant in cell membranes and is an important mediator in various biochemical pathways.2-4

Chemical Properties

White Crystalline Solid

Uses

Selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes; natural isomer of sphingosine

Uses

D-erythro-Sphingosine is used to inhibits protein kinase C and calmodulin-dependent enzymes, induces apoptosis. And also used to constituent of cell membranes.

Uses

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

Definition

cerebroside: Any one of a class ofglycolipids in which a single sugarunit is bound to a sphingolipid. The most commoncerebrosides are galactocerebrosides,containing the sugar group galactose;they are found in the plasma membranesof neural tissue and are abundantin the myelin sheaths ofneurones.

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.

Biological Activity

Inhibitor of protein kinase C and calmodulin-dependent enzymes, but may stimulate mast cells by activation of protein kinase C.

Biochem/physiol Actions

A constituent of cell membranes. Precursor of ceramide. Selective inhibitor of protein kinase C, but does not inhibit protein kinase?A or myosin light chain kinase. Inhibitor of calmodulin-dependent enzymes.

Purification Methods

D-Sphingosine is purified by recrystallisation from EtOAc, Et2O or pet ether (60-80o). It is insoluble in H2O but is soluble in Me2CO, EtOH and MeOH. It has IR bands at 1590 and 875 cm-1, and is characterised as the tribenzoate m 122-123o (from 95% EtOH). [Tipton Biochemical Preparations 9 127 1962.]

References

1) Merrill et al., (1989) Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds; Biochemistry, 28 3138 2) Ohanian and Ohanian (2001) Sphingolipids in mammalian cell signaling; Cell. Mol. Life Science, 58 2053 3) Ruvolo (2003) Intracellular signal transduction pathways activated by ceramide and its metabolites; Pharm. Res., 47 383 4) Olivier (2002) Sphingosine in apoptosis signaling; Biochim. Biophys. Acta, 1585 153

D-ERYTHRO-SPHINGOSINE Preparation Products And Raw materials

Raw materials

Preparation Products

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D-ERYTHRO-SPHINGOSINE Suppliers

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View Lastest Price from D-ERYTHRO-SPHINGOSINE manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
D-erythro-Sphingosine 123-78-4
Price
US $0.00/Kg
Min. Order
1000Kg
Purity
98.0%
Supply Ability
1kg/month
Release date
2023-02-10
BINBO BIOLOGICAL CO.,LTD
Product
Sphingosine / D-erythro-sphingosine 123-78-4
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000 kg
Release date
2024-04-25
Hebei Weibang Biotechnology Co., Ltd
Product
D-ERYTHRO-SPHINGOSINE 123-78-4
Price
US $1.00/PCS
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2021-07-28

123-78-4, D-ERYTHRO-SPHINGOSINERelated Search:

D-ERYTHRO-SPHINGOSINE, N-OCTANOYL- LIGNOCERIC CERAMIDE,C14-D-ERYTHRO-SPHINGOSINE D-ERYTHRO-SPHINGOSINE SPHINGOMYELIN (BOVINE), [CHOLINE METHYL-14C] C18-CEREBROSIDE C12 NBD-D-ERYTHRO-DIHYDROSPHINGOSINE N-Teracosanoyl-D-Spingosine C6 NBD-D-ERYTHRO-DIHYDROSPHINGOSINE C20-D-ERYTHRO-SPHINGOSINE D-ERYTHRO-SPHINGOSINE, N-PALMITOYL N-Pentadecanoyl-D-Sphingosine? N-Pentadecanoyl-psychosine? D-ERYTHRO-SPHINGOSINE, N-STEAROYLDIHYDRO,D-ERYTHRO-SPHINGOSINE, N-STEAROYL- C12 NBD-L-THREO-DIHYDROSPHINGOSINE N-Nervonoyl-D-Spingosine 6-HEXANOYL-D-ERYTHRO-SPHINGOSINE,D-ERYTHRO-SPHINGOSINE, N-HEXANOYL- D-GALACTOSYL-B1-1'-D-ERYTHRO-SPHINGOSINE LYSO-CERAMIDE TRIHEXOSIDE

  • SPHINGOSINE
  • SPHINGOSINE, C18 CHAIN
  • SPHINGOSINE, D-ERYTHRO
  • TRANS D-THREO-SPHINGOSINE
  • TRANS D-ERYTHRO-SPHINGOSINE
  • TRANS-D-ERYTHRO-2-AMINO-4-OCTADECENE-1,3-DIOL
  • BRAIN SPHINGOSINE
  • BRAIN, BOVINE
  • EGG SPHINGOSINE
  • D-SPHINGOSINE (BOVINE)
  • D-SPHINGOSINE
  • CEREBROSIDE
  • D-ERYTHRO-SPINGHOSINE
  • D-ERYTHRO-SPHINGASINE (EGG)
  • D-ERYTHRO-SPHINGOSINE
  • D-ERYTHRO-SPHINGOSINE, BOVINE
  • D-ERYTHRO-SPHINGOSINE, BOVINE BRAIN
  • D-ERYTHRO-SPHINGOSINE (BRAIN)
  • 4-SPHINGENINE
  • 2-AMINO-4-OCTADECENE-1,3-DIOL
  • D-SPHINGOSINE FROM BOVINE BRAIN &
  • D-SPHINGOSINE FROM BOVINE BRAIN*CEREBROS IDES
  • D-SPHINGOSINE FROM BOVINE BRAIN SPHINGOMYELIN*
  • 2-aminooctadec-4-ene-1,3-diol
  • D-ERYTHRO-SPHINGOSINE (1,2-13C2, 1,1-D2)
  • D-Sphingosine (from bovine brain sphinogomyelin)
  • (2S,3R,4E)-2-amino-4-Octadecene-1,3-diol
  • 4-Sphingenine, trans-D-erythro-2-Amino-4-octadecene-1,3-diol
  • D-erythro-Sphingosine (synthetic)
  • D-ERYTHRO-SPHINGOSINE, 99+%, SYNTHETICAL
  • D-erythro-Sphingosine, synthetical
  • (2S,3R,E)-2-Amino-4-octadecene-1,3-diol
  • C18-Sphingosine
  • erythro-4-Sphingenine
  • Sphingenine
  • D-erythro-Sphingosine C-18
  • Erythrosphingosine
  • trans-4-Sphingenine
  • D-erythro-Sphingosine, synthetical, 99+%
  • (2S,3R,E)-2-aMinooctadec-4-ene-1,3-diol
  • D-Sphingosine: trans-D-erythro-2-Amino-4-octadecene-1,3-diol
  • (E,2S,3R)-2-Aminooctadec-4-Ene-1,3-Diol
  • D-erythro-Sphingosine(DES)
  • D-ERYTHRO-SPHINGOSINE;SPHINGOSINE (D18:1)
  • Sphingosine (d18:1)
  • D-erythro-Sphingosine, 99+%
  • D-Sphingenine
  • D-erythro-Sphingosine, Free Base, High Purity - CAS 123-78-4 - Calbiochem
  • D-Sphingosine &gt
  • erythro-C18-Sphingosine
  • 4-Octadecene-1,3-diol, 2-amino-, (2S,3R,4E)-
  • D-erythro-Sphingosine (Erythrosphingosine)
  • 2-Aminooctadec-4-en-1,3-diol
  • D-Sphingosine/(2S,3R,E)-2-Amino-4-octadecene-1,3-diol
  • 123-78-4
  • 128-78-4
  • C15H29CHOHCHNH2CH2OH
  • C18H37NO2