D-erythro-Sphingosine

Names

[ CAS No. ]:
123-78-4

[ Name ]:
D-erythro-Sphingosine

[Synonym ]:
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

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]:

Research Areas >> Cancer

Natural Products >> Others

[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.

[Related Small Molecules]

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

MSDS

Click to get detail MSDS

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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%

Articles

Sphingosine kinase 1 contributes to leptin-induced STAT3 phosphorylation through IL-6/gp130 transactivation in oestrogen receptor-negative breast cancer.

Breast Cancer Res. Treat. 149(1) , 59-67, (2015)

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...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.