Dihydrosphingosine

Base Information

• Chemical Name: Dihydrosphingosine
• CAS No.: 6036-76-6
• Molecular Formula: C18H39NO2
• Molecular Weight: 301.513
• European Community (EC) Number: 608-571-3
• DSSTox Substance ID: DTXSID701017398
• Nikkaji Number: J36.269G
• ChEMBL ID: CHEMBL1487948
• Mol file: 6036-76-6.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 Dihydrosphingosine

Chemical Property:

• Boiling Point: 446.2±25.0 °C(Predicted)
• PKA: 12.57±0.45(Predicted)
• PSA: 66.48000
• Density: 0.927±0.06 g/cm3(Predicted)
• LogP: 4.84850
• Storage Temp.: −20°C
• Solubility.: DMSO: 25 mg/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:

97% ^*data from raw suppliers

L-erythro Sphinganine (d18:0) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(C(CO)N)O
• Isomeric SMILES: CCCCCCCCCCCCCCC[C@@H]([C@@H](CO)N)O
• Description: L-erythro Sphinganine (d18:0) is a synthetic bioactive sphingolipid and stereoisomer of sphinganine (d18:0) and D-threo sphinganine . It induces autophagy in HCT116 cells when used at a concentration of 12 μM. L-erythro Sphinganine induces cell cycle arrest of 7R4-LCB1 yeast cells. It is metabolized via sphinganine N-acyltransferase and sphinganine kinase in vivo in rat liver. [Matreya, LLC. Catalog No. 1846]

Technology Process of Dihydrosphingosine

There total 94 articles about Dihydrosphingosine 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

(+/-)-threo-2-amino-octadec-4-yne-1,3-diol

N-Benzyloxycarbonyl-D-erythro-sphingosin

Downstream raw materials:

dihydroceramide d18:0/18:1(9Z)

N-((1S,2R)-2-hydroxy-1-hydroxymethyl-heptadecyl)-lauramide

n-hexadecylaldehyde

palmitic acid

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.