D-erythro-Sphingosine

Modify Date: 2024-01-03 05:29:34

D-erythro-Sphingosine Structure
D-erythro-Sphingosine structure
Common Name D-erythro-Sphingosine
CAS Number 123-78-4 Molecular Weight 299.492
Density 0.9±0.1 g/cm3 Boiling Point 445.9±45.0 °C at 760 mmHg
Molecular Formula C18H37NO2 Melting Point 81-82ºC
MSDS Chinese USA Flash Point 223.5±28.7 °C

 Use of D-erythro-Sphingosine


D-erythro-Sphingosine is a very potent activator of p32-kinase with an EC50 of 8 μM. D-erythro-Sphingosine inhibits protein kinase C (PKC).

 Names

Name sphingosine
Synonym More Synonyms

 D-erythro-Sphingosine Biological Activity

Description D-erythro-Sphingosine is a very potent activator of p32-kinase with an EC50 of 8 μM. D-erythro-Sphingosine inhibits protein kinase C (PKC).
Related Catalog
Target

p32:8 μM (EC50)

PKC

Human Endogenous Metabolite

In Vitro A p32-sphingosine-activated protein kinase responds to low concentrations of D-erythro-Sphingosine with an initial activation observed at 2.5 μM and a peak activity at 10-20 μM. This kinase shows a modest specificity for D-erythro-Sphingosine over other sphingosine tereoisomers, and a preference for sphingosines over ihydrosphingosines[1]. D-erythro-Sphingosine inhibits protein kinase C in vitro[2]. D-erythro-Sphingosine has been shown to inhibit protein kinase C, which affects cell regulation and several signal transduction pathways, and exhibits antitumor promoter activities in various mammalian cells[3].
References

[1]. Pushkareva MYu, et al. Regulation of sphingosine-activated protein kinases: selectivity of activation by sphingoid basesand inhibition by non-esterified fatty acids. Biochem J. 1993 Sep 15;294 ( Pt 3):699-703.

[2]. Khan WA, et al. Protein kinase C and platelet inhibition by D-erythro-Sphingosine: comparison with N,N-dimethylsphingosine and commercial preparation. Biochem Biophys Res Commun. 1990 Oct 30;172(2):683-91.

[3]. Pham VT, et al. A concise synthesis of a promising protein kinase C inhibitor: D-erythro-Sphingosine. Arch Pharm Res. 2007 Jan;30(1):22-7.

 Chemical & Physical Properties

Density 0.9±0.1 g/cm3
Boiling Point 445.9±45.0 °C at 760 mmHg
Melting Point 81-82ºC
Molecular Formula C18H37NO2
Molecular Weight 299.492
Flash Point 223.5±28.7 °C
Exact Mass 299.282440
PSA 66.48000
LogP 6.40
Vapour Pressure 0.0±2.4 mmHg at 25°C
Index of Refraction 1.489
Water Solubility chloroform: 20 mg/mL

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Safety Phrases 22-24/25
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2922199090

 Synthetic Route

 Customs

HS Code 2922199090
Summary 2922199090. other amino-alcohols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

 Articles158

More Articles
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Obesity is a known risk factor for breast cancer. We have recently identified that adipokine leptin regulates the expression of a proto-oncogenic enzyme sphingosine kinase 1 (SK1). Signal transducer a...

Sphingosine kinase 1 isoform-specific interactions in breast cancer.

Mol. Endocrinol. 28(11) , 1899-915, (2014)

Sphingosine kinase 1 (SK1) is a signaling enzyme that catalyzes the formation of sphingosine-1-phosphate. Overexpression of SK1 is causally associated with breast cancer progression and resistance to ...

Fungal metabolite myriocin promotes human herpes simplex virus-2 infection.

Life Sci. 120 , 31-8, (2015)

Myriocin is a fungal metabolite with antiviral activity, including influenza, hepatitis B, and hepatitis C viruses. We investigated whether myriocin has activity against human HSV-2, one of the most p...

 Synonyms

EINECS 204-651-3
(4E)-sphing-4-enine
D-erythro-Sphingosine,synthetical
BRAIN,BOVINE
MFCD00036751
Sphingosine, D-erythro
DErySphingosine
[3H]-Sphingosine
4-trans-Sphingenine
Sphingosine
4-Sphingenine
[Fluorescein]-Sphingosine
(2S,3R,4E)-2-Aminooctadec-4-ene-1,3-diol
Sphingenine
EGG SPHINGOSINE
D-erythro-Sphingosine
D-Sphingosine
4-Octadecene-1,3-diol, 2-amino-, (2S,3R,4E)-
erythro-4-Sphingenine
CEREBROSIDE
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol
(-)-D-erythro-Sphingosine
(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-ene-1-ol
BRAIN SPHINGOSINE
(4E)-sphingenine
trans-4-sphingenine
D-erythrosphingosine
C18-Sphingosine
(2S,3R,E)-2-Amino-4-octadecene-1,3-diol
Sphingosine 2S,3R,2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol
UNII:0Y6SVQ612Q
(4E)-2-Aminooctadec-4-ene-1,3-diol
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