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;Sphingosinum;BRAIN, BOVINE;4-SPHINGENINE
- CBNumber
- CB1262764
- Molecular Formula
- C18H37NO2
- Formula Weight
- 299.49
- MOL File
- 123-78-4.mol
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
- biological source
- synthetic
- Merck
- 14,8747
- BRN
- 1727294
- Stability:
- Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
- 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
- InChIKey
- WWUZIQQURGPMPG-KRWOKUGFSA-N
- SMILES
- OC[C@@](N)([H])[C@]([H])(O)/C=C/CCCCCCCCCCCCC
- CAS DataBase Reference
- 123-78-4
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.
N-Bromosuccinimide Price
- Product number
- 44066
- Product name
- D-Sphingosine
- Purity
- ≥98.0% (TLC)
- Packaging
- 50mg
- Price
- $513
- Updated
- 2023/06/20
- Product number
- 44066
- Product name
- D-Sphingosine
- Purity
- ≥98.0% (TLC)
- Packaging
- 250mg
- Price
- $1870
- Updated
- 2023/06/20
- Product number
- S0874
- Product name
- D-Sphingosine
- Purity
- >96.0%(GC)
- Packaging
- 25mg
- Price
- $162
- Updated
- 2025/07/31
- Product number
- 10007907
- Product name
- Sphingosine (d18:1)
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $44
- Updated
- 2024/03/01
- Product number
- 10007907
- Product name
- Sphingosine (d18:1)
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $97
- Updated
- 2024/03/01
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 kinaseA 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] JR. A H M. Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds[J]. Biochemistry Biochemistry, 1989, 28 8: 3138-3145. DOI:10.1021/bi00434a004
[2] J OHANIAN V O. Sphingolipids in mammalian cell signalling.[C]//148 1. 2001: 2053-2068. DOI:10.1007/pl00000836
[3] RUVOLO P P. Intracellular signal transduction pathways activated by ceramide and its metabolites[J]. Pharmacological research, 2003, 47 5: Pages 383-392. DOI:10.1016/s1043-6618(03)00050-1
[4] CUVILLIER O. Sphingosine in apoptosis signaling[J]. Biochimica et biophysica acta. Molecular and cell biology of lipids, 2002, 1585 2: Pages 153-162. DOI:10.1016/s1388-1981(02)00336-0
D-ERYTHRO-SPHINGOSINE Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from D-ERYTHRO-SPHINGOSINE manufacturers
- Product
- D-ERYTHRO-SPHINGOSINE 123-78-4
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1000kg
- Release date
- 2025-11-06
- Product
- Sphingosine，D-ERYTHRO-SPHINGOSINE，D-Sphingosine 123-78-4
- Price
- US $0.00-0.00/kg
- Min. Order
- 0.10000000149011612kg
- Purity
- ≥90%
- Supply Ability
- 20000kgs
- Release date
- 2025-09-29
- 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