119567-63-4

Basic information

• Product Name: D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYL-
• Synonyms: 2-DIMETHYLAMINO-4-OCTADECENE-1,3-DIOL;2S-(DIMETHYLAMINO)-4E-OCTADECENE-1,3R-DIOL;DIMETHYLSPHINGOSINE;D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYL-;D-ERYTHRO-N,N-DIMETHYLSPHINGOSINE;SPHINGOSINE, N,N-DIMETHYL;N,N-DIMETHYL-D-ERYTHRO-SPHINGOSINE;N,N-DIMETHYLSPHINGOSINE
• CAS NO: 119567-63-4
• Molecular Formula: C20H41NO2
• Molecular Weight: 327.55
• Product Categories: Miscellaneous Natural Products;Protein Kinase Inhibitors and Activators
• Mol File: 119567-63-4.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 447.207 °C at 760 mmHg
• Flash Point: 14 °C
• Appearance: colorless/
• Density: 0.922 g/cm³
• Vapor Pressure: 7.07E-10mmHg at 25°C
• Refractive Index: 1.483
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• PKA: 13.72±0.20(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYL-(CAS DataBase Reference)
• NIST Chemistry Reference: D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYL-(119567-63-4)
• EPA Substance Registry System: D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYL-(119567-63-4)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 1
• Hazardous Substances Data: 119567-63-4(Hazardous Substances Data)

Usage

Description

D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYL-, also known as Dimethyl Sphingosine (d18:1) or N,N-Dimethyl-d-erythro-sphingosine (DMS), is a natural sphingolipid metabolite found in various tissues. It is a synthetic derivative of D-erythro-sphingosine and exhibits a colorless to light yellow oil appearance.

Uses

1. Used in Pharmaceutical Industry:
D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYLis used as a general modulator of protein kinases for its ability to regulate various cellular processes and potentially treat certain conditions.
2. Used in Neuropathic Pain Management:
D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYLis used as a therapeutic agent for neuropathic pain, targeting the underlying mechanisms involved in this type of pain.
3. Used in Cancer Research and Treatment:
D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYLis used as an inhibitor of sphingosine kinase (SPHK) in cancer cell lines and tissues. It has been shown to inhibit U937 cell SPHK with a Ki value of 3.1 μM and induce apoptosis in a variety of cell lines, making it a potential candidate for cancer treatment.
4. Used in Cellular Apoptosis Studies:
D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYLis used as an inducer of apoptosis, which is a process of programmed cell death. This property makes it valuable for studying the mechanisms of cell death and developing potential therapeutic strategies for various diseases.

Biochem/physiol Actions

N,N-Dimethylsphingosine (DMS) is an endogenous metabolite of sphingosine produced in various tissues and tumor cell lines. N,N-Dimethylsphingosine is a potent inhbitor of sphingosine kinase. DMS levels are elevated in the spinal cord, and contributes to allodynia, in a transected-nerve model of neuropathic pain.

References

1) Igarashi et al. (1990), A specific enhancing effect of N,N-dimethylsphingosine on epidermal growth factor receptor autophosphorylation. Demonstration of its endogenous occurrence (and the virtual absence of unsubstituted sphingosine) in human epidermoid carcinoma A431 cells; J. Biol. Chem., 265 5385 2) Yatomi et al. (1996), N,N-dimethylsphingosine inhibition of sphingosine kinase and sphingosine 1-phosphate activity in human platelets; Biochemistry, 35 626 3) Gude et al. (2008), Apoptosis induces expression of sphingosine kinase 1 to release sphingosine-1-phosphate as a “come-and-get-me” signal; FASEB J., 22 2629

InChI:InChI=1/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m0/s1