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123-78-4

Basic Information
CAS No.: 123-78-4
Name: D-ERYTHRO-SPHINGOSINE
Article Data: 120
Molecular Structure:
Molecular Structure of 123-78-4 (D-ERYTHRO-SPHINGOSINE)
Formula: C18H37NO2
Molecular Weight: 299.497
Synonyms: 4-Octadecene-1,3-diol,2-amino-, (E)-D-erythro- (8CI);4-Octadecene-1,3-diol, 2-amino-,[R-[R*,S*-(E)]]-;(-)-D-erythro-Sphingosine;(-)-Sphingosine;(2S,3R)-Sphingosine;(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol;(4E)-Sphingenine;4-Sphingenine;4-trans-Sphingenine;D-(+)-erythro-4-trans-Sphingenine;D-Sphingosine;D-erythro-C18-Sphingosine;D-erythro-Sphingosine;Erythrosphingosine;Sphingosine;erythro-4-Sphingenine;erythro-C18-Sphingosine;trans-4-Sphingenine;
EINECS: 204-651-3
Density: 0.94 g/cm3
Melting Point: 81-82 °C
Boiling Point: 445.922 °C at 760 mmHg
Flash Point: 223.486 °C
Appearance: White crystalline solid
Safety: 22-24/25
PSA: 66.48000
LogP: 4.62450
Synthetic route
105308-75-6

(2'E,4S,1'R)-4-(1'-hydroxyhexadec-2'-enyl)-1,3-oxazolidin-2-one

123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With sodium hydroxide; ethanol at 80℃; for 2.5h;100%
With sodium hydroxide In ethanol at 80℃; for 2.5h;100%
With potassium hydroxide In ethanol for 2.5h; Heating;100%
116467-63-1

N-tert-butyloxycarbonylsphingosine

123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
Stage #1: N-tert-butyloxycarbonylsphingosine With trifluoroacetic acid In dichloromethane at 50℃; for 2h;
Stage #2: With sodium hydroxide; water In dichloromethane pH=~ 10;
100%
With hydrogenchloride; water In tetrahydrofuran at 20 - 50℃; for 18h;98%
With trifluoroacetic acid for 0.5h;90%
221455-36-3

tert-butyl ((2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-octadec-4-en-2-yl)carbamate

123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 1.5h;99%
498541-46-1

(4R,5S)-2,2-Di-tert-butyl-4-((E)-pentadec-1-enyl)-[1,3,2]dioxasilinan-5-ylamine

123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran at 0℃; for 2h;98%
130967-71-4

N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide

123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
Stage #1: N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide With sodium hydroxide In ethanol at 20℃; for 2h; Inert atmosphere;
Stage #2: With water In ethanol
96%
With water; sodium hydroxide In ethanol at 20℃; for 2h;82.5%
With potassium carbonate In ethanol at 50℃; for 5h;75%
103348-49-8

2-azido-sphingosine

123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With hydrogen sulfide In pyridine; water for 48h; Ambient temperature;95%
With pyridine; hydrogen sulfide In water for 48h;95%
With sodium tetrahydroborate In isopropyl alcohol for 48h; Heating;92%

C25H43N3O5

123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 45℃; for 3h;93%
511542-07-7

(2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol

123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With ammonia; sodium In diethyl ether at -78 - 20℃; for 5h;92%

(4S,5R)-4-(hydroxymethyl)-5-(pentadec-1-en-1-yl)oxazolidin-2-one

123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 80℃; for 2h;92%
3542-12-9

(2S,3R,E)-2-aminooctadec-4-ene-1,3-diol

123-78-4

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With ammonia; lithium In tetrahydrofuran for 2h; Heating;88%
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Chemistry


IUPAC Name: (E,2S,3R)-2-aminooctadec-4-ene-1,3-diol
Molecular Formula: C18H37NO2
Molecular Weight: 299.49 g/mol
Canonical SMILES: C(=C\CCCCCCCCCCCCC)\[C@H]([C@H](CO)N)O
InChI: InChI=1/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1
Mol File: 123-78-4.mol
EINECS: 204-651-3
Product Categories: Mixed Fatty Acids; Fatty Acid Derivatives & Lipids; Glycerols; Inhibitors; Protein Kinase Inhibitors and Activators; Protein Kinase
Solubility: chloroform: 20 mg/mL, clear, colorless to very faintly yellow
Merck: 13,8821
Stability: Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
Nominal Mass: 299
Average Mass: 299.4919
Monoisotopic Mass: 299.282429
H bond acceptors: 3
H bond donors: 4
Freely Rotating Bonds: 18
Polar Surface Area: 21.7
Index of Refraction: 1.489
Molar Refractivity: 92.02 cm3
Molar Volume: 318.7 cm3
Polarizability: 36.47×10-24cm3
Surface Tension: 38.2 dyne/cm
Density: 0.939 g/cm3
Flash Point: 223.5 °C
Enthalpy of Vaporization: 81.24 kJ/mol
Boiling Point: 445.9 °C at 760 mmHg
Melting Point: 81-82 °C
storage temperature: 20 °C
logP(octanol-water): 5.530
Atmospheric OH Rate Constant: 1.34E-10 cm3/molecule-sec at 25 °C
Vapour Pressure of Sphingosine (CAS NO.123-78-4): 7.96E-10 mmHg at 25 °C

Uses

1.Sphingosine (CAS NO.123-78-4) does not inhibit protein kinase A or myosin light chain kinase;  it inhibits calmodulin-dependent enzymes; it is natural isomer of sphingosine .
2. Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid.

Safety Profile

Safety Statements: 22-24/25
S22: Do not breathe dust.  
S24/25: Avoid contact with skin and eyes.
WGK Germany of Sphingosine (CAS NO.123-78-4): 3

Specification

1.  Sphingosine (CAS NO.123-78-4), its Synonyms are 2-Aminooctadec-4-ene-1,3-diol ; 4-Octadecene-1,3-diol, 2-amino-, (R-(R*,S*-(E)))- ; (E)-2-Amino-4-octadecan-1,3-diol . It is white crystalline solid.
2. Sphingosine is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids, a class of cell membrane lipids that include sphingomyelin, an important phospholipid.