DL-erythro-Dihydrosphingosine Chemical Properties

Melting point:

70-72°C

Boiling point:

446.2±25.0 °C(Predicted)

Density 

0.927±0.06 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

chloroform/methanol (9:1): 20 mg/mL, clear, colorless to faintly yellow

pka

12.57±0.45(Predicted)

form 

Solid

color 

white

Water Solubility 

Soluble in water (partly miscible), chloroform, 100% warm ethanol (25 mg/ml), warm DMSO (25 mg/ml), and methanol.

InChI

InChI=1/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/s3

InChIKey

OTKJDMGTUTTYMP-LHIQYTEENA-N

SMILES

C(O)[C@@H](N)[C@@H](O)CCCCCCCCCCCCCCC |&1:2,4,r|

CAS DataBase Reference

3102-56-5(CAS DataBase Reference)

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

DL-erythro-Dihydrosphingosine Usage And Synthesis

Description

DL-erythro Sphinganine (d18:0) is a precursor of ceramide and sphingosine as well as a substrate of sphingosine kinases, which generate sphinganine-1-phosphate . Sphinganine levels increase significantly in response to certain mycotoxins, including fumonisins as well as in some cancers. This product is a mixture of sphinganine (d18:0) , L-erythro sphinganine (d18:0) , D-threo sphinganine (d18:0) , and L-threo sphinganine (d18:0). [Matreya, LLC. Catalog No. 1324]

Chemical Properties

White Powder

Uses

Biosynthetic precursor of sphingosine. Inhibits protein kinase C

Uses

DL-erythro-Dihydrosphingosine is an inhibitor of PKC (protein kinase C). This compound also blocks PLA2 (phospholipases A2) and the D-sphingosine precursor.

Definition

ChEBI: 2-aminooctadecane-1,3-diol is an aminodiol that is octadecane bearing two hydroxy substituents at positions 1 and 3 as well as an amino substituent at position 2. It is a sphingoid and an aminodiol.

Biological Functions

Sphingosine (Sph) is emerging as an intracellular regulator of cellular differentiation and apoptosis. Three stereoisomers,d-erythro-Sph,l-threo-Sph, and dl-erythro-dihydrosphingosine, were tested in the induction of apoptosis and inhibition of MAPK activity in three different kinds of solid tumour cell lines. d-erythro-Sph was strongest in these effects among the three compounds. l-threo-Sphingosine was partly active. On the other hand,dl-erythro-dihydrosphingosine was inactive[1].

Biological Activity

Protein kinase C inhibitor.

storage

-20°C (desiccate)

Purification Methods

Purify it by recrystallisation from pet ether/EtOAc or CHCl3. The (±)-N-dichloroacetyl derivative has m 142-144o (from MeOH). [Shapiro et al. J Am Chem Soc 80 2170 1958, Shapiro & Sheradsky J Org Chem 28 2157 1963.] The D-isomer crystallises from pet ether/Et2O and has m 78.5-79o, [] 28 +6o (CHCl3/MeOH, 10:1). [Grob & Jenny Helv Chim Acta 35 2106 1953, Jenny & Grob Helv Chim Acta 36 1454 1953, Beilstein 4 I 448, 4 II 757, 4 III 854, 4 IV 1887.]

References

[1] Chouhei Sakakura . “Selectivity of Sphingosine-Induced Apoptosis.” Biochemical and biophysical research communications 246 3 (1998): Pages 827-830.

DL-erythro-Dihydrosphingosine(3102-56-5)Related Product Information

• N-(6-[(7-NITRO-2-1,3-BENZOXADIAZOL-4-YL)AMINO]CAPROYL)-PHYTOSPHINGOSINE
• Phytosphingosine
• C2 DIHYDROCERAMIDE
• C14 Dihydroceramide
• DL-ERYTHRO-DIHYDROSPHINGOSINE
• C12 NBD-L-THREO-DIHYDROSPHINGOSINE
• C6 NBD-D-ERYTHRO-DIHYDROSPHINGOSINE
• C6 NBD-L-THREO-DIHYDROSPHINGOSINE
• C12 NBD-D-ERYTHRO-DIHYDROSPHINGOSINE
• D-ERYTHRO-SPHINGOSINE
• D-erythro-Dihydro-D-sphingosine-1-phosphate
• C6 DIHYDROCERAMIDE
• KRN7000
• C8 DIHYDROCERAMIDE
• C6 NBD SAFINGOL
• C18 Dihydroceramide
• C4 Dihydroceramide
• N-[12-[(7-NITRO-2-1,3-BENZOXADIAZOL-4-YL)AMINO]DODECANOYL]-SPHINGANINE