 |
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| 1 |  |
N-Palmitoyl-D,L-Dihydrosphingomyelin |
PSP3095 | Keizo Waku |
C39H81N2O7P | 721.043 | |
224-225  C (Ref. 3017) |
This compound was synthesized from N-palmitoyl-3-O-benzoyl-D,L-sphinganin with b-bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017) |
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| 2 |  |
N-Oleoyl-D,L-Dihydrosphingomyelin |
PSP3096 | Keizo Waku |
C41H85N2O7P | 749.097 | |
208-210 C (Ref. 3017) |
This compound was synthesized from N-oleoyl-3-O-benzoyl-D,L-sphinganine with b -bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017) |
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| 3 |  |
N-(2'D,L-Hydroxypalmitoyl)D,L-Dihydrosphingomyelin |
PSP3097 | Keizo Waku |
C39H83N2O7P | 723.059 | |
228-230 C (Ref. 3017) |
This compound was synthesized from N-(2'D,L-Hydroxypalmitoyl)-3-O-benzoyl-D,L-sphinganine with b -bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017) |
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| 4 |  |
N-(trans-2-Hexadecenoyl)-D,L-Dihydrosphingomyelin |
PSP3098 | Keizo Waku |
C39H81N2O7P | 721.043 | |
205-206 C (Ref. 3017) |
This compound was synthesized from N-(trans-2-hexadecenoyl)-3-O-benzoyl-D,L-sphinganine with b-bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017) |
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| 5 |  |
N-Palmitoyl-D,L-Sphingomyelin |
PSP3099 | Keizo Waku |
C39H79N2O6P | 703.028 | |
209-210 C (Ref. 3017) |
This compound was synthesized from N-palmitoyl-3-O-benzoyl-D,L-sphingenine with b -bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017) |
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| 6 |  |
N-Oleoyl-D,L-Sphingomyelin |
PSP3100 | Keizo Waku |
C41H83N2O7P | 747.081 | |
188-190 C (Ref. 3017) |
This compound was synthesized from N-palmitoyl-3-O-benzoyl-D,L-sphinganin with b -bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine. (Ref. 3017) |
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| 7 |  |
N-(2'DL-Hydroxypalmitoyl)-D,L-Sphingomyelin |
PSP3101 | Keizo Waku |
|
219-221 C (Ref. 3017) |
This compound was synthesized from N-(2'DL-hydroxypalmitoyl)-3-O-benzoyl-D,L-sphingenine with |
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| 8 |  |
Dihydrosphingomyelin |
dihydroceramide-1-phosphorylcholine |
PSP5012 | Kentaro Hanada |
DSM |
|
insoluble in water; solble in chloroform |
Ubiquitous in mammalian (probably ubiquitous in vertebrates)(Ref. 5001) |
DSM is formed by phosphorylcholine transfer from phosphatidylcholine to dihydroceramide. In general, the DSM level in cells is lower than the level of sphingomyelin.(Ref. 5002) |
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| 9 |  |
Sphingomyelin |
Ceramide-1-phosphorylcholine |
PSP5013 | Kentaro Hanada |
SM |
|
Essential for mammlian cell growth(Ref. 5037/5038) Formation of detergent-resistant lipid-rafts(Ref. 5039/5040) A reservoir of ceramide in ceramide-mediated signalling(Ref. 5017/5035/5036) Anti-colon cancer effect of dietary SM(Ref. 5041) Influences on cholesterol metabolism(Ref. 5042/5043) In hibition of lecthin-cholesterol acyltransferase activity(Ref. 5044) Interaction between cells and substrata(Ref. 5045) Binding to procollagen(Ref. 5046) A receptor to lysenin (an earthworm-derived cytolysin)(Ref. 5047/5038) |
196-198 C(Ref. 5012) |
+6 to 7 (in chloroform/methanol)(Ref. 5012) |
insoluble in water, diethylether, acetone soluble in chloroform, hot ethanol, hot ethylacetate(Ref. 5012) |
Ubiquitous in mammalian (probably ubiquitous in vertebtates) |
SM is formed by phosphorylcholine transfer from phosphatidylcholine to ceramide. SM is degradated to ceramide by acid sphingomyelinase in lysosome, or by neutral sphingomyelinase in the plasma membrane.(Ref. 5002) |
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| 10 |  |
sphingosine 1-phosphate |
PSP6001 | Takehiko Yokomizo |
S1P/ SPP/ Sph-1-P |
C18H38NO5P | 379.472 | |
Acts either extracellularly on Edg receptors (Edg1, 3, 5, 6, 8) (Ref. 6005/6007) or intracellularly to cause pleiotropic biological responses (Ref. 6004). Mobilizes intracellular calcium (Ref. 6004). Decreases cAMP. Suppresses ceramide-mediated apoptosis (Ref. 6006). Activates MAP kinasse and phospholipase D (Ref. 6001/6005). Inhibits chemotactic motility and invasiveness of tumor cells (Ref. 6002). Stimulates cell growth (Ref. 6003). |
It is difficult to suspend S1P using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution. The solubility of stock solutions may be increased by the addition of dimethylamine. |
ESI/MS (Ref. 4509). |
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| 11 |  |
lysosphingomyelin |
sphingosylphosphorylcholine |
PSP6002 | Takehiko Yokomizo |
SPC |
C23H49N2O5P | 464.619 | |
Mobilizes intracellular calcium stores (Ref. 6008) probably via several G protein-coupled receptors, such as OGR1 and GPR4 (Ref. 6014/6015). It regulates numerous cellular functions including cell proliferation (Ref. 6009), cell growth inhibition, smooth muscle contraction, neurite outgrowth (Ref. 6010), and actin rearrangement (Ref. 6013). Activates MAP kinase (Ref. 6012) and transcription factor AP-1 (Ref. 6011). |
It is difficult to suspend SPC using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution. The solubility of stock solutions may be increased by the addition of dimethylamine. |
ESI/MS (Ref. 4509). |
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| 12 |  |
D-erythro-sphinganine-1-phosphate |
dihydrosphingosine-1-phosphate |
PSP6003 | Takehiko Yokomizo |
DHS-1-P/ HSPP |
C18H40NO5P | 381.488 | |
Saturated analog of sphingosine-1-phosphate displaying 20-fold lower activity (Binds to Edg1 receptor but not functional) (Ref. 6017/6018/6019). Induces chemotaxis in HUVECs (Ref. 6018). May be used as a negative control for intracellular effects of sphingosine-1-phosphate. Stimulate proliferation and resistance to stress in yeast (Ref. 6021/6022). |
It is difficult to suspend sphinganine-1-phosphate using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution. The solubility of stock solutions may be increased by the addition of dimethylamine. |
Synthesized by sphinganine kinase, and dephosphorylated by sphingosine phosphatase (Ref. 6016). |
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| 13 |  |
phytosphingosine -1-phosphate |
4-hydroxy-D-erythro-sphinganine-1-phosphate |
PSP6004 | Takehiko Yokomizo |
PHS-1-P |
C18H40NO6P | 397.487 | |
It is difficult to suspend phytosphingosine-1-phosphate using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution. The solubility of stock solutions may be increased by the addition of dimethylamine. |
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| 14 |  |
C8 Ceramide-1-phosphate |
D-erythro-C8 ceramide-1-phosphate |
PSP6005 | Takehiko Yokomizo |
C8 ceramide-1-P |
C26H52NO6P | 505.668 | |
Soluble in DMSO and ethanol. |
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| 15 |  |
PSP8001 | Akira Hayashi |
CAEPn |
|
IR of CAEPn, pressed in KBr (Ref. 8004); |
GC-MS of TMS-2-aminoethylphosphonic acid and of TMS-ceramides obtained from CAEP (Ref. 8001); GC-MA of TMS-CAEP (long-chain base originated ions and ceramide originated ions) (Ref. 8001); FAB-MS of CAEP (m/z 126 ion, long-chain base ions, ceramide ions and [M+H] + ions in positive ion mode and m/z 124 ion and [M-H]- ions in negative ion mode(Ref. 8002/8003) |
Oyster visceral tissues (Ref. 8004); Oyster adductor (Ref. 8001); Euhadra hickonis (Ref. 0005); Oyster (Ostrea gigas), adductor (+++), gills (+++), mantle (+++) and viscera (+++) (Ref. 8003/8006/8012/8019) Protozoa , Tetrahymena pyriformis W (+) (Ref. 8006/8010/8019); Protozoa, Tetrahymena pyriformis WH-14(++) (Ref. 8006/8013/8019); Mollusca, Liolophura japonica (++) (Ref. 8006/8012/8019); Mollusca, Tegla lischkei (+) (Ref. 8006/8012/8019); Mollusca, Conomurex luhuanun (+++) (Ref. 8006/8012/8019); Mollusca, Cellanaeucosmia (+++) (Ref. 8006/8012/8019); Mollusca, Mytilus edulis (+++) (Ref. 8006/8012/8019); Mollusca, Hyriopsis schlegelli, Ova (++) (Ref. 8013/8006/8019), spermatozoa (++) (Ref. 8006/8014/8015/8019); Scallop, Hennifes giganteum (+++) (Ref. 8006/8016/8019); Pink abalone, Haliotis corrugata (++) (Ref. 8006/8016/8019); Coelenterata, Anthopleura elegantissima (+++) (Ref. 8006/8017/8019); Coelenterata, Metridium senile (++) (Ref. 8006/8018/8019) |
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| 16 |  |
N-Hexadecanoyl-hexadecasphingosine 2-aminoethylphosphonate (Ref. 8001) |
PSP8002 | Akira Hayashi |
C16:0-d16:1-AEPn |
C34H69O5N2P1 | 616.896 | |
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| 17 |  |
N-Heptadecanoyl-4-hexadecasphingenine 2-aminoethylphosphonate (Ref. 8001) |
PSP8003 | Akira Hayashi |
C17:0-d16:1-AEPn |
C36H72O5N2P1 | 643.941 | |
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| 18 |  |
N-Octadecanoyl-4,8-sphingadienine 2-aminoethylphosphonate (Ref. 8001) |
PSP8004 | Akira Hayashi |
C18:0-d18:2-AEPn |
C38H74O5N2P1 | 669.978 | |
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| 19 |  |
N-Octadecanoyl-4-sphingosine 2-aminoethylphosphonate (Ref. 8001) |
PSP8005 | Akira Hayashi |
C18:0-d18:1-AEPn |
C35H70O5N2P1 | 629.915 | |
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| 20 |  |
N-Hexadecanoyl 4-sphingosine 2-aminoethylphosphonate (Ref. 8003) |
PSP8006 | Akira Hayashi |
C16:0-d18:1-AEPn |
C36H72O5N2P1 | 643.941 | |
Oyster adductor, mantle, gills and viscera (Ref. 8003) |
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| 21 |  |
N-Hexadecanoyl-4, 8-sphingadienine 2-aminoethylphosphonate (Ref. 8003) |
PSP8007 | Akira Hayashi |
C16:0-d18:2-AEPn |
C36H70O5N2P1 | 641.925 | |
Oyster adductor, gills, mantle and viscera (Ref. 8003) |
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| 22 |  |
PSP8008 | Akira Hayashi |
CMAEPn |
|
Turbo cornutus (Ref. 8008/8009); Viscera of Turbo cornutus (Ref. 8007); Protozoa, Tetrahymena pyriformis W (++) (Ref. 8006/8010/8019); Protozoa, Tetrahymena pyriformis WH-14 (+) (Ref. 8006/8011/8019); Mollusca, Liolophura japonica (+) (Ref. 8006/8012/8019); Mollusca, Turbo cornutus, muscle (+++), viscera (+++) (Ref. 8006/8012/8019); Mollusca, Monodonta labio (+++) (Ref. 8006/8012/8019); Mollusca, Tegli lischkei (++) (Ref. 8006/8012/8019); Mollusca, Hiriopsis schlegelli, ova (+) (Ref. 8006/8013/8019), spermatozoa (+) (Ref. 8006/8014/8012/8019); Coelenterata, Metridium senile (+) (Ref. 8006/8018/8019); Land snail, Euhadra hickonis (Ref. 8005) |
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| 23 |  |
N-Hexadecanoyl-hexadecasphinga-4-enine 2-N-methylaminoethylphosphonate (Ref. 8009) |
PSP8009 | Akira Hayashi |
C16:0-d16:1-MAEPn |
C35H70O5N2P1 | 629.915 | |
GC-EI-MS of TMS-Ceramide (C16:0-d16:1) (Ref. 8009) |
Viscera of Turbo cornutus (Ref. 8009) |
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| 24 |  |
N-Hexadecanoyl heptadeca-4-sphingenine 2-N-methylaminoethylphosphonate (Ref. 8009) |
PSP8010 | Akira Hayashi |
C16:0-d17:1-MAEPn |
C36H72O5N2P1 | 643.941 | |
GC-EI-MA of TMS-Ceramide (C16:0-d17:1) (Ref. 8009) |
Viscera of Turbo Cornutus (Ref. 8009) |
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| 25 |  |
N-Hexadecanoyl branched sphingosine 2-N-methylaminoethylphosphonate (Ref. 8009) |
PSP8011 | Akira Hayashi |
C16:0-br-d18:1-MAEPn |
C37H74O5N2P1 | 657.968 | |
GC-EI-MS of TMS-Ceramide (C16:0-br-d18:1) (Ref. 8009) |
Viscera of Turbo Cornutus (Ref. 8009) |
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| 26 |  |
N-Hexadecanoylsphingosine 2-N-methylaminoethylphosphonate (Ref. 8009) |
PSP8012 | Akira Hayashi |
C16:0-d18:1-MAEPn |
C37H74O5N2P1 | 657.968 | |
GC-EI-MS of TMS-ceramide (C16:0-br-d18:1) (Ref. 8009) |
Viscera of Turbo cornutus (Ref. 8009) |
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| 27 |  |
N-Hexadecanoyl sphingadienine 2-N-methylaminoethylphosphonate (Ref. 8009) |
PSP8013 | Akira Hayashi |
c16:0-d18:2-MAEPn |
C37H72O5N2P1 | 655.952 | |
GC-EI-MS- of TMS-Ceramide (C16:0-d18:1) (Ref. 8009) |
Viscera of Turbo cornutus (Ref. 8009) |
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| 28 |  |
N-Hexadecanoyldocosasphingadienine 2-N-methylaminoethylphosphonate (Ref. 8009) |
PSP8014 | Akira Hayashi |
C16:0-d22:2-MAEPn |
C41H80O5N2P1 | 712.058 | |
GC-EI-MS of TMS-Ceramide (C16:0-d22:2) (Ref. 8009) |
Viscera of Turbo cornutus (Ref. 8009) |
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| 29 |  |
N-2-Hydroxyhexadecanoylphytosphingosine 2-N-methylaminoethylphosphonate (Ref. 8008) |
PSP8015 | Akira Hayashi |
h-C16:0-t18:0-MAEPn |
C37H77O7N2P1 | 692.990 | |
GC-EI-MS of TMS-ceramide (h-C16:0-t18:0) (Ref. 8008) |
Viscera of Turbo cornutus (Ref. 8008) |
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| 30 |  |
N-2-hydroxyhexadecanoyl-4-hydroxynonadecasphinganine 2-N-methyaminoethylphosphonate (Ref. 8008) |
PSP8016 | Akira Hayashi |
h-C16:0-t19:0-MAEPn |
C38H79O7N2P1 | 707.017 | |
GC-EI-MS of TMS-Ceramide (h-C16:0-t19:0) (Ref. 8008) |
Viscera of Turbo cornutus (Ref. 8008) |
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| 31 |  |
N-2-Hydroxyhexadecanoyl-4-hydroxydocosasphingenine 2-N-methylaminoethylphosphonate (Ref. 8008) |
PSP8017 | Akira Hayashi |
h-C16:0-t22:1-MAEPn |
C41H83O7N2P1 | 747.081 | |
GC-EI-MS of TMS-Ceramide (h-C16:0-t22:1) (Ref. 8008) |
ViscerA of Turbo cornutus (Ref. 8008) |
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