N-(9Z-octadecenoyl)-sphinganine

Base Information

• Chemical Name: N-(9Z-octadecenoyl)-sphinganine
• CAS No.: 34227-83-3
• Molecular Formula: C36H71 N O3
• Molecular Weight: 565.965
• UNII: ZBD7T2NL63
• DSSTox Substance ID: DTXSID501314764
• Nikkaji Number: J621.126G
• Wikidata: Q27144410
• Metabolomics Workbench ID: 30661
• Mol file: 34227-83-3.mol

Synonyms:34227-83-3;N-(9Z-octadecenoyl)-sphinganine;N-oleoyl-D-erythro-sphinganine;C18:1-Dihydroceramide;N-Oleoyl sphinganine;C18:1DH Cer;N-oleoylsphinganine;Cer(d18:0/18:1(9Z));N-(oleoyl)-dihydroceramide;ZBD7T2NL63;(Z)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]octadec-9-enamide;N-[(9Z)-octadecenoyl]sphinganine;N-(9Z-octadecenoyl)-dihydroceramide;Oleamide, N-(2-hydroxy-1-(hydroxymethyl)heptadecyl)-, D-erythro-;195151-15-6;C18:1 Dihydroceramide (d18:0/18:1(9Z));Ceramide d36:1;N-C18:1 sphinganine;N-oleoyldihydrosphingosine;N-(oleoyl)dihydroceramide;UNII-ZBD7T2NL63;SCHEMBL1478978;CHEBI:74100;MJQIARGPQMNBGT-WWUCIAQXSA-N;DTXSID501314764;N-(9Z-octadecenoyl)dihydroceramide;LMSP02020015;N-[(9Z)-octadecenoyl]dihydrosphingosine;Q27144410;(9Z)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]octadec-9-enamide;D-ERYTHRO-1,3-DIHYDROXY-2-(CIS-9-OCTADECENOYLAMIDO)OCTADECANE;(9Z)-N-((1S,2R)-2-HYDROXY-1-(HYDROXYMETHYL)HEPTADECYL)-9-OCTADECENAMIDE;9-OCTADECENAMIDE, N-((1S,2R)-2-HYDROXY-1-(HYDROXYMETHYL)HEPTADECYL)-, (9Z)-;9-Octadecenamide, N-[(1R,2S)-2-hydroxy-1-(hydroxymethyl)heptadecyl]-, (9Z)-rel-;9-Octadecenamide,N-[(1R,2S)-2-hydroxy-1-(hydroxymethyl)heptadecyl]-,(9Z)-rel-;C18:1 Dihydroceramide (d18:0/18:1(9Z)), N-oleoyl-D-erythro-sphinganine, powder

Chemical Property of N-(9Z-octadecenoyl)-sphinganine

Chemical Property:

• Vapor Pressure: 2.59E-22mmHg at 25°C
• Boiling Point: 694.5°C at 760 mmHg
• PKA: 14.30±0.20(Predicted)
• Flash Point: 373.8°C
• PSA: 73.05000
• Density: 0.915g/cm³
• LogP: 11.18350
• XLogP3: 13.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 32
• Exact Mass: 565.54339513
• Heavy Atom Count: 40
• Complexity: 536

Purity/Quality:

99% ^*data from raw suppliers

N-OLEOYL-D-ERYTHRO-SPHINGANINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(C(CO)NC(=O)CCCCCCCC=CCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCCCC[C@H]([C@H](CO)NC(=O)CCCCCCC/C=C\CCCCCCCC)O

Technology Process of N-(9Z-octadecenoyl)-sphinganine

There total 4 articles about N-(9Z-octadecenoyl)-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: 86.5%

methyl oleate (methyl cis-9-octadecenoate) + (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) → dihydroceramide d18:0/18:1(9Z) (34227-83-3)

Guidance literature:

Reference yield:

(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) + sorbitan monooleate (5938-38-5) → dihydroceramide d18:0/18:1(9Z) (34227-83-3)

Guidance literature:

With Novozym 435; at 90 ℃; for 24h; Enzymatic reaction;

Reference yield:

(Z)-9-octadecenoyl chloride (112-77-6) + (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) → dihydroceramide d18:0/18:1(9Z) (34227-83-3)

Guidance literature:

With pyridine; N,N-dimethyl-formamide;

DOI:10.1021/ja01550a061

upstream raw materials:

(Z)-9-octadecenoyl chloride

(2S,3R)-2-amino-1,3-octadecanediol

sorbitan monooleate