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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:: 2024/10/28 23:16:16

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DL-erythro-Dihydrosphingosine Properties

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)

SAFETY

Risk and Safety Statements

WGK Germany	3

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

Global( 86)Suppliers

Supplier	Tel	Country	ProdList	Advantage	Inquiry
Chongqing Zhihe Biopharmaceutical Co., Ltd.	+86-18580541567 +86-17782035140	China	212	58	Inquiry
Shaanxi Dideu Medichem Co. Ltd	+86-029-81138252 +86-18789408387	China	3937	58	Inquiry
Shenzhen Nexconn Pharmatechs Ltd	+86-755-89396905 +86-15013857715	China	10406	58	Inquiry
TargetMol Chemicals Inc.	+1-781-999-5354 +1-00000000000	United States	32239	58	Inquiry
Dideu Industries Group Limited	+86-29-89586680 +86-15129568250	China	22855	58	Inquiry
Alfa Chemistry		United States	24072	58	Inquiry
Changzhou AniKare Pharmatech Co., Ltd.	+86-0519-8359-8696 +8618018249389	China	9875	58	Inquiry
Aladdin Scientific		United States	52924	58	Inquiry
TargetMol Chemicals Inc.	+8613564774135	United States	19897	58	Inquiry
LGC Standards	+44 (0)20 8943 8480	United Kingdom	6494	0	Inquiry

Supplier	Advantage
Chongqing Zhihe Biopharmaceutical Co., Ltd.	58
Shaanxi Dideu Medichem Co. Ltd	58
Shenzhen Nexconn Pharmatechs Ltd	58
TargetMol Chemicals Inc.	58
Dideu Industries Group Limited	58
Alfa Chemistry	58
Changzhou AniKare Pharmatech Co., Ltd.	58
Aladdin Scientific	58
TargetMol Chemicals Inc.	58
LGC Standards	0

3102-56-5(DL-erythro-Dihydrosphingosine)Related Search:

N-(6-[(7-NITRO-2-1,3-BENZOXADIAZOL-4-YL)AMINO]CAPROYL)-PHYTOSPHINGOSINE Phytosphingosine C2 DIHYDROCERAMIDE C14 Dihydroceramide DL-ERYTHRO-DIHYDROSPHINGOSINE

C12 NBD-L-THREO-DIHYDROSPHINGOSINE C6 NBD-D-ERYTHRO-DIHYDROSPHINGOSINE C6 NBD-L-THREO-DIHYDROSPHINGOSINE C12 NBD-D-ERYTHRO-DIHYDROSPHINGOSINE D-ERYTHRO-SPHINGOSINE

D-erythro-Dihydro-D-sphingosine-1-phosphate C6 DIHYDROCERAMIDE KRN7000 C8 DIHYDROCERAMIDE C6 NBD SAFINGOL

C18 Dihydroceramide C4 Dihydroceramide N-[12-[(7-NITRO-2-1,3-BENZOXADIAZOL-4-YL)AMINO]DODECANOYL]-SPHINGANINE

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DL-ERYTHRO-2-AMINO-1,3-OCTADECANEDIOL DL-ERYTHRO-DIHYDROSPHINGOSINE D,L-ERYTHRO-SPHINGANINE DL-SPHINGANINE D-ERTYTHRO-SPHINGANINE, C18 CHAIN D-ERYTHRO-SPHINGOSINE, DIHYDRO- DIHYDROSPHINGOSINE, D-ERYTHRO [R-(R*,S*)]-2-aminooctadecane-1,3-diol Dihydrosphingosine,Racemic,Synthetic 1,3-Octadecanediol, 2-amino-, (2S,3R)- (2S,3R)-2-amino-1,3-Octadecanediol DL-Erythro-DIHYDROSPHINGOSINE Synthetic DL-erythro-1,3-Dihydroxy-2-aminooctadecane, DL-erythro-2-Amino-1,3-octadecanediol, DL-Sphinganine DL-erythro/threo Sphinganine (d18:0) 1,3-Octadecanediol, 2-amino-, (2R,3S)-rel- DL-ERYTHRO-DIHYDROSPHINGOSINE USP/EP/BP DL-ERYTHRO-1,3-DIHYDROXY-2-AMINOOCTADECANE D-ERYTHRO-DIHYDROSPHINGOSINE D-ERYTHRO-SPHINGANINE DIHYDROSPHINGOSINE Phytosphingosine 55%/D-erythro-Dihydrosphingosine 20% mixture D,L-erythro-Dihydrosphingosine, sphingosine kinase inhibitor, PKC inhibitor 3102-56-5 BioChemical Biochemicals and Reagents Enzymes, Inhibitors, and Substrates Enzyme Inhibitors Enzyme Inhibitors by Enzyme P to Q Protein kinase C Phospholipase A 2 Sphingolipids Sphingoid bases Sphinganines Lipids Miscellaneous Natural Products pharmacetical Protein Kinase Inhibitors and Activators Protein Kinase