3102-56-5

Basic information

• Product Name: DL-ERYTHRO-DIHYDROSPHINGOSINE
• Synonyms: DL-ERYTHRO-1,3-DIHYDROXY-2-AMINOOCTADECANE;DL-ERYTHRO-2-AMINO-1,3-OCTADECANEDIOL;DL-ERYTHRO-DIHYDROSPHINGOSINE;D,L-ERYTHRO-SPHINGANINE;DL-SPHINGANINE;D-ERYTHRO-DIHYDROSPHINGOSINE;D-ERYTHRO-SPHINGANINE;D-ERTYTHRO-SPHINGANINE, C18 CHAIN
• CAS NO: 3102-56-5
• Molecular Formula: C₁₈H₃₉NO₂
• Molecular Weight: 301.51
• EINECS: 212-116-0
• Product Categories: Miscellaneous Natural Products;pharmacetical;Protein Kinase Inhibitors and Activators;Protein Kinase
• Mol File: 3102-56-5.mol
• Article Data: 47

Chemical Properties

• Melting Point: 70-72°C
• Boiling Point: 446.2°C at 760 mmHg
• Flash Point: 223.7°C
• Appearance: white/
• Density: 0.927g/cm³
• Vapor Pressure: 7.75E-10mmHg at 25°C
• Refractive Index: 1.477
• Storage Temp.: −20°C
• Solubility: chloroform/methanol (9:1): 20 mg/mL, clear, colorless to fa
• PKA: 12.57±0.45(Predicted)
• Water Solubility: Soluble in water (partly miscible), chloroform, 100% warm ethanol (25 mg/ml), warm DMSO (25 mg/ml), and methanol.
• CAS DataBase Reference: DL-ERYTHRO-DIHYDROSPHINGOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: DL-ERYTHRO-DIHYDROSPHINGOSINE(3102-56-5)
• EPA Substance Registry System: DL-ERYTHRO-DIHYDROSPHINGOSINE(3102-56-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 3102-56-5(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
DL-ERYTHRO-DIHYDROSPHINGOSINE is used as a biochemical precursor for the synthesis of ceramide and sphingosine, which are essential components of cell membranes and have crucial roles in cellular processes.
Used in Cancer Research:
DL-ERYTHRO-DIHYDROSPHINGOSINE is used as a research compound to study its role in the development and progression of certain cancers, as its levels increase significantly in response to mycotoxins and in some cancerous conditions.
Used in Enzyme Inhibition:
DL-ERYTHRO-DIHYDROSPHINGOSINE is used as an inhibitor of protein kinase C (PKC) and phospholipases A2 (PLA2), making it a valuable tool in studying the functions and regulation of these enzymes in various biological processes.
Used in Pharmaceutical Development:
DL-ERYTHRO-DIHYDROSPHINGOSINE is used as a potential therapeutic agent in the development of drugs targeting protein kinase C and phospholipases A2, which are implicated in various diseases and disorders.
Used in Analytical Chemistry:
DL-ERYTHRO-DIHYDROSPHINGOSINE is used as a reference compound in the development and validation of analytical methods for the detection and quantification of ceramide, sphingosine, and related metabolites in biological samples.
Used in Cosmetics Industry:
DL-ERYTHRO-DIHYDROSPHINGOSINE is used as an active ingredient in cosmetic products for its potential skin health benefits, such as improving skin barrier function and reducing inflammation.
Used in Food Industry:
DL-ERYTHRO-DIHYDROSPHINGOSINE is used as a natural preservative and emulsifier in the food industry, due to its ability to inhibit certain enzymes and its role in maintaining cell membrane integrity.

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.]

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+/m1/s1

Upstream product

• 105617-34-3 (2S,3R)-2-amino-1,3-dihydroxyoctadec-4-yne 
• 502925-03-3 (4S,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-((Z)-pentadec-3-enyl)-2-phenyl-4,5-dihydro-oxazole 
• 1606993-84-3 ethyl (4R,5R)-2-oxo-5-pentadecyloxazolidine-4-carboxylate 
• 14663-15-1 (+/-)-erythro-2-benzylamino-octadecane-1,3-diol 
• 131606-77-4 (2S,3R)-2-[(tert-butoxycarbonyl)amino]-1,2-O-N-isopropylideneoctadecane-1,3-diol 
• 263558-70-9 ethyl (2R,3R)-2-azido-3-hydroxyoctadecanoate 
• 158021-50-2 (2S,3R)-2-azido-1,3-octadecanediol 
• 97975-08-1 1-<(N-benzylcarbamoyl)oxy>-trans-2,3-epoxyoctadecane 
• 98048-64-7 (2S,3R)-2-benzylamino-1,3-octadecanediol 
• 81306-31-2 (2R,3R)-2,3-epoxyoctadecan-1-ol 
• 3173-56-6 benzyl isothiocyanate 
• 75355-78-1 (2S,3R)-erythro-2-phthalimidooctadecane-1,3-diol 
• 140408-14-6 (2S,3R)-N-(tert-butoxycarbonyl)-<2-amino-1,3-dihydroxyoctadecane> 
• 13031-64-6 (2S,3R)-2-acetylaminooctadecan-1,3-diol 

Downstream Products

• 629-80-1 n-hexadecylaldehyde 
• 1002-84-2 palmitic acid 
• 57-10-3 1-hexadecylcarboxylic acid 
• 21275-74-1 dihydroceramide 
• 156159-44-3 (2S,2'R,3R,3'E)-N-(2'-t-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-O-isopropyliden-<2-amino-1,3-dihydroxyoctadecane> 
• 156257-69-1 (2S,2'R,3R,3'E)-N-(2'-t-butyldiphenylsilyloxy-3'-octadecenoyl)-<2-amino-1,3-dihydroxyoctadecane> 
• 156159-45-4 (2S,2'S,3R,3'E)-N-(2'-t-butyldiphenylsilyloxy-3'-octadecenoyl)-<2-amino-1,3-dihydroxyoctadecane> 
• 21481-56-1 (2S,3R)-2-octadecanoylaminooctadecane-1,3-diol 
• 554-62-1 D-ribo-phytosphingosine 
• 111149-09-8 N-palmitoyl-D-ribo-phytosphingosine 
• 6036-86-8 (-)-L-threo-sphinganine 
• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 
• 6036-76-6 (2R,3S)-2-aminooctadecane-1,3-diol 
• 34227-83-3 dihydroceramide d18:0/18:1(9Z) 

Relevant articles and documents

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Short asymmetric syntheses of sphinganine [(2S,3R)-2-aminooctadecane-1,3-diol] and its C(2)-epimer

A short asymmetric synthesis of sphinganine [(2S,3R)-2-aminooctadecane-1,3-diol] and its C(2)-epimer is reported. The synthesis of sphinganine employs diastereoselective aminohydroxylation of tert-butyl 2-octadecenoate [conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide, then in situ enolate oxidation with (+)-camphorsulfonyloxaziridine (CSO)] and a stereospecific rearrangement of the resultant anti-α-hydroxy-β-amino ester into the corresponding anti-α-amino-β-hydroxy ester. Final hydrogenolysis and ester reduction completes the synthesis of the sphingoid base target. The synthesis of the C(2)-epimer follows a similar route, incorporating a diastereoselective reduction protocol to transform the anti-α-hydroxy-β-amino ester into its syn-α-hydroxy-β-amino ester counterpart.

Multicomponent cis- and trans-Aziridinatons in the Syntheses of All Four Stereoisomers of Sphinganine

All four stereoisomers of sphinganine can be synthesized by a multicomponent aziridination of an aldehyde, an amine and an α-diazo carbonyl compound mediated by a BOROX catalyst with high asymmetric induction (≥96% ee). The threo isomers are available from ring-opening of cis-aziridines by an oxygen nucleophile with inversion at the C-3 position and the erythro-isomers are likewise available from trans-aziridines.