D-Sphingosine
| Code | Size | Price |
|---|
| CDX-D0559-M025 | 25 mg | £103.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
Short term: +4°C, Long term: -20°C
Documents
Further Information
Alternate Names/Synonyms:
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol; D-erythro-Sphingosine C-18; (-)-Sphingosine
Appearance:
White powder.
CAS:
123-78-4
EClass:
32160000
Form (Short):
solid
Handling Advice:
Protect from light and moisture.
InChi:
InChI=1S/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
InChiKey:
WWUZIQQURGPMPG-KRWOKUGFSA-N
Long Description:
Chemical. CAS: 123-78-4. Formula: C18H37NO2. MW: BD9837. D-Sphingosine is a characteristic structural unit of many sphingolipids such as ceramides, gangliosides, globosides, sulfatides, sphingomyelin, and others. It is most abundant in nervous tissue and cell membranes. Sphingosine with an 18-carbon chain and a double bond at carbon 4 is the most abundant sphingosine in animal tissues. D-Sphingosine inhibits protein kinase C and phosphatidic acid phosphohydrolase, whereas it activates phospholipase D, diacylglycerol (DAG) kinase and the cation channel TRPM3. Phosphorylation of sphingosine by sphingosine kinases 1 and 2 (SPHK 1, SPHK 2) produces sphingosine-1-phosphate, a potent bioactive lipid that exhibits a broad spectrum of biological activities including cell proliferation, survival, migration, cytoskeletal organization and morphogenesis.
MDL:
MFCD00036751
Molecular Formula:
C18H37NO2
Molecular Weight:
299.49
Package Type:
Vial
Product Description:
D-Sphingosine is a characteristic structural unit of many sphingolipids such as ceramides, gangliosides, globosides, sulfatides, sphingomyelin, and others. It is most abundant in nervous tissue and cell membranes. Sphingosine with an 18-carbon chain and a double bond at carbon 4 is the most abundant sphingosine in animal tissues. D-Sphingosine inhibits protein kinase C and phosphatidic acid phosphohydrolase, whereas it activates phospholipase D, diacylglycerol (DAG) kinase and the cation channel TRPM3. Phosphorylation of sphingosine by sphingosine kinases 1 and 2 (SPHK 1, SPHK 2) produces sphingosine-1-phosphate, a potent bioactive lipid that exhibits a broad spectrum of biological activities including cell proliferation, survival, migration, cytoskeletal organization and morphogenesis.
Purity:
> 97% (TLC)
SMILES:
OC[C@@](N)([H])[C@]([H])(O)/C=C/CCCCCCCCCCCCC
Solubility Chemicals:
Soluble in ethanol, DMSO, methanol or chloroform (10mg/ml). Insoluble in water.
Source / Host:
Synthetic
Transportation:
Non-hazardous
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
(1) W.A. Khan, et al.; BBRC 172, 683 (1990) | (2) W.A. Khan, et al.; Biochem. J. 278, 387 (1991) | (3) Y.A. Hannun, et al.; Biochemistry 40, 4893 (2001) | (4) Y. Takuwa, et al.; J. Biochem. 131, 767 (2002) | (5) M.J. Kluk & T. Hla; Biochim. Biophys. Acta 1582, 72 (2002) | (6) I. Ishii, et al.; Annu. Rev. Biochem. 73, 321 (2004) | (7) H. Nakamura, et al.; Eur. J. Pharmacol. 484, 9 (2004) | (8) C. Grimm, et al.; Mol. Pharmacol. 67, 798 (2005) | (9) V.T. Pham, et al.; Arch. Pharm. Res. 30, 22 (2007) | (10) K. Held, et al.; Temperature 2, 201 (2015)