DL-erythro-Dihydrosphingosine
- CAS No.
- 3102-56-5
- Chemical Name:
- DL-erythro-Dihydrosphingosine
- Synonyms
- DIHYDROSPHINGOSINE;D-ERYTHRO-SPHINGANINE;D-ERYTHRO-DIHYDROSPHINGOSINE;DL-ERYTHRO-1,3-DIHYDROXY-2-AMINOOCTADECANE;DL-SPHINGANINE;D,L-ERYTHRO-SPHINGANINE;DL-ERYTHRO-DIHYDROSPHINGOSINE;DIHYDROSPHINGOSINE, D-ERYTHRO;D-ERYTHRO-SPHINGOSINE, DIHYDRO-;D-ERTYTHRO-SPHINGANINE, C18 CHAIN
- CBNumber:
- CB6139144
- Molecular Formula:
- C18H39NO2
- Molecular Weight:
- 301.51
- MOL File:
- 3102-56-5.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/11 15:28:25
| 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 |
| InChIKey | OTKJDMGTUTTYMP-LHIQYTEENA-N |
| SMILES | C(O)[C@@H](N)[C@@H](O)CCCCCCCCCCCCCCC |&1:2,4,r| |
| CAS DataBase Reference | 3102-56-5(CAS DataBase Reference) |
DL-erythro-Dihydrosphingosine Chemical Properties,Uses,Production
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
Uses
DL-erythro-Dihydrosphingosine is an inhibitor of PKC (protein kinase C). This compound also blocks PLA2 (phospholipases A2) and the D-sphingosine precursor.
Biological Functions
Sphingosine (Sph) is emerging as an intracellular regulator of cellular differentiation and apoptosis. Three stereoisomers,d-erythro-Sph,l-threo-Sph, and dl-erythro-dihydrosphingosine, were tested in the induction of apoptosis and inhibition of MAPK activity in three different kinds of solid tumour cell lines. d-erythro-Sph was strongest in these effects among the three compounds. l-threo-Sphingosine was partly active. On the other hand,dl-erythro-dihydrosphingosine was inactive[1].
Biological Activity
Protein kinase C inhibitor.
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.]
References
[1] Chouhei Sakakura . “Selectivity of Sphingosine-Induced Apoptosis.” Biochemical and biophysical research communications 246 3 (1998): Pages 827-830.
DL-erythro-Dihydrosphingosine Preparation Products And Raw materials
Raw materials
Preparation Products
DL-erythro-Dihydrosphingosine Suppliers
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Chongqing Zhihe Biopharmaceutical Co., Ltd. | +86-18580541567 +86-17782035140 | China | 301 | 58 | Inquiry |
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| Dideu Industries Group Limited | +86-29-89586680 +86-15129568250 | China | 24639 | 58 | Inquiry |
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| Changzhou AniKare Pharmatech Co., Ltd. | +86-0519-8359-8696 +8618018249389 | China | 8661 | 58 | Inquiry |
| Aladdin Scientific | +1-+1(833)-552-7181 | United States | 52927 | 58 | Inquiry |
| LGC Standards | +44 (0)20 8943 8480 | United Kingdom | 6495 | 0 | Inquiry |
| Sichuan Wei Keqi Biological Technology Co., Ltd. | 028-81700200 18116577057 | China | 7887 | 56 | Inquiry |
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