Dihydrosphingosine

Base Information

• Chemical Name: Dihydrosphingosine
• CAS No.: 3102-56-5
• Molecular Formula: C18H39 N O2
• Molecular Weight: 301.513
• Hs Code.: 2922199090
• European Community (EC) Number: 608-571-3
• DSSTox Substance ID: DTXSID701017398
• Nikkaji Number: J36.269G
• ChEMBL ID: CHEMBL1487948
• Mol file: 3102-56-5.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:

• 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
• Solubility.: chloroform/methanol (9:1): 20 mg/mL, clear, colorless to fa
• Water Solubility.: Soluble in water (partly miscible), chloroform, 100% warm ethanol (25 mg/ml), warm DMSO (25 mg/ml), and methanol.
• 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%min ^*data from raw suppliers

Dihydrosphingosine ^*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: 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]
• Uses: Biosynthetic precursor of sphingosine. Inhibits protein kinase C DL-erythro-Dihydrosphingosine is an inhibitor of PKC (protein kinase C). This compound also blocks PLA2 (phospholipases A2) and the D-sphingosine precursor.

Technology Process of Dihydrosphingosine

There total 89 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:

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

N-Benzyloxycarbonyl-D-erythro-sphingosin

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

D-erythro-1-β-D-galactopyranosyloximethyl-2-tetracosanoylamino-octadecan-3-ol

Downstream raw materials:

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

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

n-hexadecylaldehyde

palmitic acid

Refernces

• 1、 Da Silva Pinto, Solange,Davies, Stephen G.,Fletcher, Ai M.,Newton, Sophie K.,Roberts, Paul M.,Thomson, James E.. "Short asymmetric syntheses of sphinganine [(2S,3R)-2-aminooctadecane-1,3-diol] and its C(2)-epimer". supporting information. . Retrieved 2021/02/09.
• 2、 Touge, Taichiro,Kuwana, Masahiro,Komatsuki, Yasuhiro,Tanaka, Shigeru,Nara, Hideki,Matsumura, Kazuhiko,Sayo, Noboru,Kashibuchi, Yoshinobu,Saito, Takao. "Development of Asymmetric Transfer Hydrogenation with a Bifunctional Oxo-Tethered Ruthenium Catalyst in Flow for the Synthesis of a Ceramide (D-erythro-CER[NDS])". supporting information. p. 452 - 461. Retrieved 2019/01/04.