Sphingosine supplier | CasNO.123-78-4

Name
D-ERYTHRO-SPHINGOSINE
EINECS 204-651-3
CAS No. 123-78-4
Article Data120
CAS DataBase
Density 0.94 g/cm³
Solubility
Melting Point 81-82 °C
Formula C₁₈H₃₇NO₂
Boiling Point 445.922 °C at 760 mmHg
Molecular Weight 299.497
Flash Point 223.486 °C
Transport Information
Appearance White crystalline solid
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 185681-41-8
(E)-(1S,2R)-2-Benzyloxy-1-benzyloxymethyl-heptadec-3-enylamine

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With ammonia; sodium In tetrahydrofuran at -78℃; for 0.5h;	88%

: 1094213-80-5
(2S,3R)-(4E)-1-(tert-butyldiphenylsilyloxy)-2-phthalimido-octadec-4-en-3-ol

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
Stage #1: (2S,3R)-(4E)-1-(tert-butyldiphenylsilyloxy)-2-phthalimido-octadec-4-en-3-ol With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: With hydrazine In methanol for 6h; Reflux; Inert atmosphere;	87%

: (2R,3R,E)-ethyl 2-amino-3-hydroxyoctadec-4-enoate hydrochloride

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With sodium tetrahydroborate; water In ethanol at 0℃; for 72h;	86%

: 133859-61-7
(2S,3R,4E)-2-Amino-3-benzyloxymethoxy-1-hydroxy-4-octadecene

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With lithium; triethylamine In tetrahydrofuran at -78℃; for 3h;	85%

: 850223-35-7
(E)-(2S,3R)-2-Amino-3-benzyloxy-octadec-4-en-1-ol

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With ammonia; sodium In tetrahydrofuran at -78℃; for 0.5h; Birch reduction;	85%

: 572922-39-5
2-phenyl-4-(S)-[(1R,2E)-1-(trimethylsilanyl-oxy)hexadec-2-enyl]-1,3-oxazoline

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
Stage #1: 2-phenyl-4-(S)-[(1R,2E)-1-(trimethylsilanyl-oxy)hexadec-2-enyl]-1,3-oxazoline With hydrogenchloride; water In tetrahydrofuran for 18h; Stage #2: With sodium hydroxide; water In methanol for 2h; Heating / reflux;	85%
Stage #1: 2-phenyl-4-(S)-[(1R,2E)-1-(trimethylsilanyl-oxy)hexadec-2-enyl]-1,3-oxazoline With hydrogenchloride In tetrahydrofuran at 20℃; for 18h; Stage #2: With sodium hydroxide In methanol for 0.666667h; Heating;	79%

: 78739-31-8
threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ2-oxazoline

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
Stage #1: threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ2-oxazoline With hydrogenchloride In tetrahydrofuran; water for 3h; Stage #2: With sodium hydroxide In methanol; water for 1h; Reflux;	85%

: 198009-73-3
[(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-heptadec-3-enyl]-carbamic acid tert-butyl ester

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With trifluoroacetic acid for 16h; Ambient temperature;	83%

: 115464-03-4
tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
Stage #1: tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate With hydrogenchloride; water In tetrahydrofuran at 75℃; for 12h; Inert atmosphere; Stage #2: With sodium hydroxide In water pH=12; Inert atmosphere;	82%
With hydrogenchloride In methanol for 2h; Ambient temperature;	34%
With hydrogenchloride

: 148289-52-5
(2S,3R)-2-amino-1,3-(dibenzyloxy)-octadeca-4-ene

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With ammonia; sodium In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	80%

: (3aR,5R,6R,6aR)-6-Azido-2,2-dimethyl-5-((E)-pentadec-1-enyl)-tetrahydro-furo[2,3-d][1,3]dioxole

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
Stage #1: (3aR,5R,6R,6aR)-6-Azido-2,2-dimethyl-5-((E)-pentadec-1-enyl)-tetrahydro-furo[2,3-d][1,3]dioxole With water; trifluoroacetic acid at 25℃; for 2.5h; Stage #2: With sodium periodate In water; acetone at 0 - 30℃; for 2.5h; Stage #3: With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; for 2h;	79%

: 128751-66-6
[4S-[4α,5α(E)]]-4-(hydroxymethyl)-5-(1-pentadecenyl)-2-oxazolidinone

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 80℃; for 2h;	77.5%
With sodium hydroxide In ethanol at 80℃; for 2.5h;

: 299172-62-6
(+)-tert-butyl {(1S,2R,3E)-2-Hydroxy-1-[(trityloxy)methyl]heptadec-3-en-1-yl}carbamate

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 3h;	76%

: 178550-59-9
(S)-4-((E)-(R)-1-Methoxymethoxy-hexadec-2-enyl)-3-methoxymethyl-oxazolidin-2-one

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With sodium hydroxide In ethanol for 20h; Heating;	73%

: 105617-34-3
(2S,3R)-2-amino-1,3-dihydroxyoctadec-4-yne

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In 1,2-dimethoxyethane for 12h; Heating;	70%
With sodium bis(2-methoxyethoxy)aluminium dihydride In diethyl ether at 0℃; for 24h; Reduction;	69%

: (S)-tert-Butyl 4-((R,E)-1-hydroxyhexadec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
Stage #1: (S)-tert-Butyl 4-((R,E)-1-hydroxyhexadec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate With hydrogenchloride; methanol; water for 1.5h; Heating / reflux; Stage #2: With sodium hydroxide In methanol; water	68%

: 1438399-43-9
C26H50N2O3S

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With borane-ammonia complex; lithium diisopropyl amide In tetrahydrofuran; hexane at 0 - 25℃; Inert atmosphere;	65%

: 3102-57-6
N-acetyl-D-erythro-sphingosine

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With hydrazine hydrate at 90℃; for 20h;	60%

: 2482-37-3
(2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In methanol	60%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 764-22-7, 2304-75-8, 3102-56-5, 3102-60-1, 6036-76-6, 6036-86-8, 13552-09-5, 15639-50-6, 73938-69-9
(2S,3R)-2-amino-1,3-octadecanediol

Conditions

Conditions	Yield
With hydrogen; 10percent Pd/C In methanol at 24℃; under 760.051 Torr; for 7.5h; Catalytic hydrogenation;	100%
With hydrogen; platinum(IV) oxide In methanol for 2.16667h;	98%
With 1,4-dioxane; platinum Hydrogenation;
With hydrogen; platinum In ethanol
With hydrogen

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 108-24-7
acetic anhydride

: 2482-37-3
(2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene

Conditions

Conditions	Yield
With pyridine	100%
With pyridine at 20℃; for 2h;	99%
With pyridine at 0 - 20℃; for 18h;	99%

: 112668-54-9
ω-azido-hexadecanoic acid

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 1298053-54-9
ceramide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;	99%
With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;	85%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 108-24-7
acetic anhydride

: 3102-57-6
N-acetyl-D-erythro-sphingosine

Conditions

Conditions	Yield
In ethanol for 1h; Ambient temperature;	97%
In methanol for 0.5h; Ambient temperature;	85%
With methanol

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 24424-99-5
di-tert-butyl dicarbonate

: 116467-63-1
N-tert-butyloxycarbonylsphingosine

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane; water for 0.5h; Ambient temperature;	97%
With triethylamine In 1,4-dioxane; water at 20℃; for 0.5h;	97%
With triethylamine In 1,4-dioxane; water chemoselective reaction;	96%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 7584-85-2, 7792-96-3, 30048-41-0, 66701-54-0, 71328-30-8, 103531-01-7, 149342-82-5
β-D-galactopyranosyl-(1->4)-α-D-glucopyranosyl fluoride

: 109785-20-8
O-(β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→1)-(2S, 3R, 4E)-2-aminooctadec-4-ene-1,3-diol

Conditions

Conditions	Yield
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 20℃; pH=5.0; Enzymatic reaction;	97%
With Rhodococcus sp. strain M-777 endoglycoceramidase II glycosynthase mutant E351S/D314Y In 1,2-dimethoxyethane at 37℃; for 72h; pH=5.3; Sonication; Enzymatic reaction;	95%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 7-(4-(p-tolyldiazenyl)phenyl)heptanoic acid

: N-(7-(4-(p-tolyldiazenyl)phenyl)heptanamide)-(2S,3R)-2-aminooctadec-4-ene-1,3-diol

Conditions

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In ethyl acetate at 20℃; for 4h; Inert atmosphere;	97%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 658-78-6
1-nitro-4-trifluoroacetoxy-benzene

: 130967-71-4
N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide

Conditions

Conditions	Yield
With pyridine for 15h; Ambient temperature;	96%

: (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6S)-6-((2R,3S,4R,5R,6R)-6-Fluoro-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 126550-86-5
globotriaosylsphingosine

Conditions

Conditions	Yield
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 20℃; pH=5.0; Enzymatic reaction;	96%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 73782-15-7
16-bromohexadecanoyl chloride,

: 886213-05-4
D-erythro-2-N-(16'-bromohexadecanoyl)-sphingosine

Conditions

Conditions	Yield
With sodium acetate In tetrahydrofuran; water at 20℃; for 0.333333h;	96%
With sodium acetate In tetrahydrofuran; water at 20℃; for 0.433333h;	96%

: 5-acetylamino-2-[2-(6-fluoro-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-4-hydroxy-6-(1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 94458-63-6
O-(5-Acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl)-(1->4)-O-β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 37℃; for 12h; pH=5.0; Enzymatic reaction;	95%

: C37H61FN2O28

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 94458-59-0
β-D-galactopyranosyl-(1→3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1→4)-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→1)-(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Conditions

Conditions	Yield
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 20℃; pH=5.0; Enzymatic reaction;	95%

: 933058-16-3
6-tetramethylrhodamine-(N-hydroxysuccinimidyl-β-alanine)-amide

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: C46H62N4O7

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In chloroform; water; N,N-dimethyl-formamide for 15h;	95%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 103531-01-7
β-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl fluoride

: (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-((E)-(2S,3R)-2-Amino-3-hydroxy-octadec-4-enyloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Conditions

Conditions	Yield
With endoglycoceramidase II E351S mutant glycosynthase; Triton X-100 In acetate buffer at 20℃; pH=5.0; Enzymatic reaction;	94%

: imidazole-1-sulfonyl azide hydrochloride

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 103348-49-8
2-azido-sphingosine

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; potassium carbonate In methanol at 20℃; for 12h;	94%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 101442-77-7
α-azidohexadecanoic acid

: C34H66N4O3

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;	94%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 15-(9Z,12Z-octadecadienoyloxy)pentadecanoic acid

: 15-(9Z,12Z-octadeca-9,12-dienoyloxy)pentadecanoic acid (2-hydroxy-1-(hydroxymethyl)heptadec-3-en-yl)amide

Conditions

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	93.4%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 15-(octadecyloxy)pentadecanoic acid

: 15-(octadecyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

Conditions

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	93.2%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 103348-49-8
2-azido-sphingosine

Conditions

Conditions	Yield
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 30℃; for 3h;	93%
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃; for 3h;	93%
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃; for 3h;	93%
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃;
With imidazole-1-sulfonyl azide hydrochloride; copper(II) sulphate hydrate In methanol at 20℃; for 12h;

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 69186-31-8
15-acetoxypentadecanoic acid

: 15-(acetoxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

Conditions

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	93%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 30-{[(10RS)-16,16,16-d3-10-(methyl-d3)hexadecanoyl]oxy}triacontanoic acid

: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]-30-{[(10RS)-16,16,16-d3-10-(methyl-d3)hexadecanoyl]oxy}triacontanamid

Conditions

Conditions	Yield
Stage #1: 30-{[(10RS)-16,16,16-d3-10-(methyl-d3)hexadecanoyl]oxy}triacontanoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.25h; Stage #2: (2S,3R,4E)-2-amino-4-octadecene-1,3-diol In dichloromethane at 20℃; for 16h;	93%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 15-(dodecyloxy)pentadecanoic acid

: 15-(dodecyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

Conditions

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	92.4%

: 123-78-4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

: 1020733-53-2
15-(pentyloxy)pentadecanoic acid

: 15-(pentyloxy)pentadecanoic acid(2-hydroxy-1-hydroxymethyl-heptadecyl-3-en-yl)amide

Conditions

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;	92.1%

Sphingosine Chemical Properties

IUPAC Name: (E,2S,3R)-2-aminooctadec-4-ene-1,3-diol
Molecular Formula: C₁₈H₃₇NO₂Molecular 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

Sphingosine 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.

Sphingosine 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

Sphingosine 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.

Product Name

D-ERYTHRO-SPHINGOSINE

Synthetic route

Sphingosine Chemical Properties

Sphingosine Uses

Sphingosine Safety Profile

Sphingosine Specification

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