DL-erythro-Dihydrosphingosine

Synonym(s):Sphinganine

CAS NO.：3102-56-5
Empirical Formula: C18H39NO2
Molecular Weight: 301.51
MDL number: MFCD00079141
EINECS: 608-571-3
SAFETY DATA SHEET (SDS)
Update Date: 2026-05-11 16:31:51

DL-erythro-Dihydrosphingosine Structural

What is DL-erythro-Dihydrosphingosine?

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

The Uses of DL-erythro-Dihydrosphingosine

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

The Uses of DL-erythro-Dihydrosphingosine

Biosynthetic precursor of sphingosine. Inhibits protein kinase C

What are the applications of Application

DL-erythro-Dihydrosphingosine is an inhibitor of PKC and PLA2

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 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.]

Properties of DL-erythro-Dihydrosphingosine

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
form	Solid
pka	12.57±0.45(Predicted)
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
CAS DataBase Reference	3102-56-5(CAS DataBase Reference)