3102-56-5 Usage
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
Different sources of media describe the Uses of 3102-56-5 differently. You can refer to the following data:
1. Biosynthetic precursor of sphingosine. Inhibits protein kinase C
2. DL-erythro-Dihydrosphingosine is an inhibitor of PKC (protein kinase C). This compound also blocks PLA2 (phospholipases A2) and the D-sphingosine precursor.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 3102-56-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,0 and 2 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 3102-56:
(6*3)+(5*1)+(4*0)+(3*2)+(2*5)+(1*6)=45
45 % 10 = 5
So 3102-56-5 is a valid CAS Registry Number.
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
3102-56-5Relevant articles and documents
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Shapiro,D.,Sheradsky,T.
, p. 2157 (1963)
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Short asymmetric syntheses of sphinganine [(2S,3R)-2-aminooctadecane-1,3-diol] and its C(2)-epimer
Da Silva Pinto, Solange,Davies, Stephen G.,Fletcher, Ai M.,Newton, Sophie K.,Roberts, Paul M.,Thomson, James E.
supporting information, (2021/02/09)
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
Zhou, Yubai,Mukherjee, Munmun,Gupta, Anil K.,Wulff, William D.
, p. 2230 - 2233 (2017/05/12)
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.
