Sphinganine

Base Information

• Chemical Name: Sphinganine
• CAS No.: 764-22-7
• Molecular Formula: C₁₈H₃₉NO₂
• Molecular Weight: 301.513
• European Community (EC) Number: 212-116-0
• UNII: YT0ZSD64HM
• DSSTox Substance ID: DTXSID501016568
• Nikkaji Number: J14.383I
• Wikidata: Q27088847
• Pharos Ligand ID: 8BCJ8D6QG9QY
• Metabolomics Workbench ID: 30476
• ChEMBL ID: CHEMBL448741
• Mol file: 764-22-7.mol

Synonyms:2-aminooctadecane-1,3-diol;dihydrosphingosine;erythro-D-sphinganine;safingol;safingol hydrochloride;safingol, ((R*,S*)-(+-))-isomer;safingol, (R-(R*,R*))-isomer;safingol, (S-(R*,S*))-isomer;saginfol;SPC 100270;SPC-100270;sphinganine;threo-dihydrosphingosine

Chemical Property of Sphinganine

Chemical Property:

• Vapor Pressure: 7.75E-10mmHg at 25°C
• Melting Point: 70-72°C
• Boiling Point: 446.2°C at 760 mmHg
• PKA: 12.57±0.45(Predicted)
• Flash Point: 223.7°C
• PSA: 66.48000
• Density: 0.927g/cm³
• LogP: 4.84850
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: soluble25mg/mL (warm)
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 16
• Exact Mass: 301.298079487
• Heavy Atom Count: 21
• Complexity: 200

Purity/Quality:

98%,99%, ^*data from raw suppliers

D-erythro-C18-Dihydro-D-sphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(C(CO)N)O
• Isomeric SMILES: CCCCCCCCCCCCCCC[C@H]([C@H](CO)N)O
• Description: Dihydrosphingosine (764-22-7) is a biosynthetic precursor of sphingosine. Inhibitor of protein kinase C1?and phospholipases A2 and D2.
• Uses: Sphinganine (d18:0) has been used:as a standard in liquid chromatography tandem mass spectrophotometry for the quantification of epidermal ceramidesas a medium supplement to test its effect on growth of yeast cellsin the preparation of bovine serum albumin lipid complex to investigate its effect on non-lysosomal - glucosylceramidase β2 (GBA2) inhibition Biosynthetic precursor of Sphingosine. Inhibits protein kinase C.

Technology Process of Sphinganine

There total 77 articles about Sphinganine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → (2S,3R)-2-amino-1,3-octadecanediol (764-22-7,2304-75-8,3102-56-5,3102-60-1,6036-76-6,6036-86-8,13552-09-5,15639-50-6,73938-69-9)

Guidance literature:

With hydrogen; 10percent Pd/C; In methanol; at 24 ℃; for 7.5h; under 760.051 Torr;

DOI:10.1021/ja994215o

Reference yield: 99.0%

dibenzyl 1-((2S,3R,E)-1-(benzyloxy)-3-hydroxyoctadec-5-en-2-yl)hydrazine-1,2-dicarboxylate (1463440-03-0) → (2S,3R)-2-amino-1,3-octadecanediol (764-22-7,2304-75-8,3102-56-5,3102-60-1,6036-76-6,6036-86-8,13552-09-5,15639-50-6,73938-69-9)

Guidance literature:

With hydrogen; acetic acid; In methanol; at 20 ℃; for 8h; under 3102.97 Torr;

DOI:10.1039/c3ra43048k

Reference yield: 98.0%

(2S,3R)-N-(tert-butoxycarbonyl)-<2-amino-1,3-dihydroxyoctadecane> (140408-14-6) → (2S,3R)-2-amino-1,3-octadecanediol (764-22-7,2304-75-8,3102-56-5,3102-60-1,6036-76-6,6036-86-8,13552-09-5,15639-50-6,73938-69-9)

Guidance literature:

With hydrogenchloride; In ethyl acetate; for 0.5h;

upstream raw materials:

dihydrosphingosine

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

N-Benzyloxycarbonyl-D-erythro-sphingosin

(+/-)-erythro-2-benzylamino-octadecane-1,3-diol

Downstream raw materials:

n-hexadecylaldehyde

palmitic acid

1-hexadecylcarboxylic acid

(-)-L-threo-sphinganine

Refernces

• 1、 Ashley, Ben,Campopiano, Dominic J.,Chamberlain, Joshua D.,Coleman, Aimiyah,D’Emilia, Rachel,Fu, Larina,Guan, Ziqiang,Hansen, Matthew E. B.,Klein, Eric A.,Mohan, Eric C.,Nguyen, Hung,Stankeviciute, Gabriele,Tang, Peijun. "Convergent evolution of bacterial ceramide synthesis". . . Retrieved 2022/01/06.
• 2、 Zhou, Yubai,Mukherjee, Munmun,Gupta, Anil K.,Wulff, William D.. "Multicomponent cis- and trans-Aziridinatons in the Syntheses of All Four Stereoisomers of Sphinganine". . p. 2230 - 2233. Retrieved 2017/05/12.