D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYL- Chemical Properties

Boiling point:

447.2±45.0 °C(Predicted)

Density 

0.921±0.06 g/cm3(Predicted)

Flash point:

14 °C

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)

form 

Waxy solid/Clear oil

color 

colorless

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

119567-63-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

F

Risk Statements 

11

Safety Statements 

7-16

RIDADR 

UN 1170 3/PG 2

WGK Germany 

1

MSDS

• Language:English Provider:SigmaAldrich

D-ERYTHRO-SPHINGOSINE, N,N-DIMETHYL- Usage And Synthesis

Description

N,N-Dimethylsphingosine (119567-63-4) is a synthetic derivative of D-erythro-sphingosine (Cat.# 10-2287). Endogenous sphingolipid.1?Inhibits sphingosine kinase (IC50 = 5 μM).2?N,N-Dimethylsphingosine induces apoptosis in a variety of cell lines.3

Chemical Properties

Colourless to Light Yellow Oil

Uses

D-erythro-N,N-Dimethylsphingosine is general modulator of protein kinases . D-erythro-N,N-Dimethylsphingosine is implicated in neuropathic pain.

Uses

N,N-Dimethylsphingosine is an inhibitor of sphingosine kinase (SPHK). It is a natural metabolite of sphingosine in some cancer cell lines and tissues. N,N-Dimethylsphingosine inhibited U937 cell SPHK with a Ki value of 3.1 μM. N,N-Dimethylsphingosine induces apoptosis, but it is not an inhibitor of protein kinase C.

Uses

A general modulator of protein kinases.

Definition

ChEBI: N,N-dimethylsphingosine is a sphingoid that is sphingosine in which the two amino hydrogens are replaced by methyl groups. It has a role as a metabolite and an EC 2.7.1.91 (sphingosine kinase) inhibitor. It is an aminodiol, a sphingoid and a tertiary amino compound. It is functionally related to a sphingosine. It is a conjugate base of a N,N-dimethylsphingosine(1+).

General Description

Dimethyl Sphingosine (d18:1), also called as N,N-Dimethyl-d-erythro-sphingosine (DMS), is a natural sphingolipid metabolite. It is found in various tissues.

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

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