N-oleoyl-D-erythro-sphingosine - ≥98% , CAS No.5966-28-9

CAS: 5966-28-9 Cat. No.: N130623 Molecular Weight: 563.938 Beilstein Registry Number: 6283861 PubChem CID: 5283563

GRADE & PURITY ≥98%

Synonyms

C18:1 Ceramide (d18:1/18:1(9Z)) | N-Oleoyl-D-erythro-Sphingosine Ceramide C18:1 | AKOS037645154 | C18:1 Ceramide (d18:1/18:1(9Z)), N-oleoyl-D-erythro-sphingosine, powder | n-oleoylsphingosine | N-oleoyl-sphingosine | N-[(9Z)-octadecenoyl]sphingosine | CHE

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

N-Oleoyl-D-erythro-sphingosine is a member of the ceramide family, acting as a signaling molecule with its proapoptotic function among the most studied.

General description：

C18:1 Ceramide (d18:1/18:1(9Z)) or N-oleoyl-D-erythro-sphingosine is a synthetic ceramide containing sphingosine with oleic acid.

application：

C18:1 Ceramide (d18:1/18:1(9Z)) may be used as a standard:

to quantify ceramide content in muscle tissue samples using high-performance liquid chromatography/tandem mass spectrometry (HPLC/MS2)

for the absolute quantification of epidermal lipids using liquid chromatography-tandem mass spectrometry (LC/MS/MS)

for the ratiometric quantification of sphingomyelin (SM)

Specifications

Synonyms

C18:1 Ceramide (d18:1/18:1(9Z)) | N-Oleoyl-D-erythro-Sphingosine Ceramide C18:1 | AKOS037645154 | C18:1 Ceramide (d18:1/18:1(9Z)), N-oleoyl-D-erythro-sphingosine, powder | n-oleoylsphingosine | N-oleoyl-sphingosine | N-[(9Z)-octadecenoyl]sphingosine | CHE

Specifications & Purity

≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCC=CC(C(CO)NC(=O)CCCCCCCC=CCCCCCCCC)O
• IUPAC Name: (Z)-N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octadec-9-enamide
• InChIKey: OBFSLMQLPNKVRW-RHPAUOISSA-N
• INCHI: 1S/C36H69NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h17-18,29,31,34-35,38-39H,3-16,19-28,30,32-33H2,1-2H3,(H,37,40)/b18-17-,31-29+/t34-,35+/m0/s1
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCCCCCC/C=C\CCCCCCCC)O
• PubChem CID: 5283563
• Molecular Weight: 563.938
• Beilstein: 6283861

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Sphingolipids
      • Subclass Ceramides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Sphingolipids
• Subclass: Ceramides
• Intermediate Tree Nodes: Not available
• Direct Parent: Long-chain ceramides
• Alternative Parents: N-acyl amines Secondary carboxylic acid amides Secondary alcohols Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Long-chain ceramide - Fatty amide - N-acyl-amine - Fatty acyl - Carboxamide group - Secondary alcohol - Secondary carboxylic acid amide - Carboxylic acid derivative - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Alcohol - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as long-chain ceramides. These are ceramides bearing a long chain fatty acid.
• External Descriptors: N-acylsphingosines (ceramides)

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in DMSO, chloroform, DMF, and 100% Ethanol.
• Molecular Weight: 563.900 g/mol
• XLogP3: 13.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 31
• Exact Mass: 563.528 Da
• Monoisotopic Mass: 563.528 Da
• Topological Polar Surface Area: 69.600 Ų
• Heavy Atom Count: 40
• Formal Charge: 0
• Complexity: 574.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1