N-oleoyl-D-erythro-sphinganine - ≥99% , CAS No.34227-83-3

CAS: 34227-83-3 Cat. No.: N130686 Molecular Weight: 565.954

GRADE & PURITY ≥99%

Synonyms

34227-83-3|N-(9Z-octadecenoyl)-sphinganine|N-oleoyl-D-erythro-sphinganine|C18:1-Dihydroceramide|N-Oleoyl sphinganine|C18:1DH Cer|Cer(d18:0/18:1(9Z))|N-(oleoyl)-dihydroceramide|ZBD7T2NL63|(Z)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]octadec-9-enamide|N-[(9Z)

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

General description

C18:1 Dihydroceramide (d18:0/18:1(9Z)) is a synthetic lipid. Dihydroceramide belongs to the ceramide family. It contains sphinganine, which is devoid of the 4,5-trans-double bond in the sphingoid base backbone.

application

C18:1 Dihydroceramide (d18:0/18:1(9Z)) has been used as an internal standard to quantify the levels of serum and skeletal muscle lipids extracted from muscle tissue by liquid chromatography-mass spectrometry (MS) analysis. It has also been used as an standard to study its structural characterization by positive-ionization mode 193 nm ultraviolet photodissociation (UVPD)-mass spectrometry/MS.

 

Specifications

Synonyms

34227-83-3 | N-(9Z-octadecenoyl)-sphinganine | N-oleoyl-D-erythro-sphinganine | C18:1-Dihydroceramide | N-Oleoyl sphinganine | C18:1DH Cer | Cer(d18:0/18:1(9Z)) | N-(oleoyl)-dihydroceramide | ZBD7T2NL63 | (Z)-N-[(2S, 3R)-1, 3-dihydroxyoctadecan-2-yl]octadec-9-enamide | N-[(9Z)

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Dihydroceramide is synthesized by the N-acylation of dihydrosphingosine. It functions as an inactive precursor for ceramide in de-novo sphingolipid synthesis. (Dihydro)-ceramide desaturase catalyzes the conversion of dihydroceramide to ceramide by the add

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

≥99%

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCCCC(C(CO)NC(=O)CCCCCCCC=CCCCCCCCC)O
• IUPAC Name: (Z)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]octadec-9-enamide
• InChIKey: MJQIARGPQMNBGT-WWUCIAQXSA-N
• INCHI: 1S/C36H71NO3/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/h17-18,34-35,38-39H,3-16,19-33H2,1-2H3,(H,37,40)/b18-17-/t34-,35+/m0/s1
• Isomeric SMILES: CCCCCCCCCCCCCCC[C@H]([C@H](CO)NC(=O)CCCCCCC/C=C\CCCCCCCC)O
• Molecular Weight: 565.954
• Reaxy-Rn: 1717533
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1717533&ln=

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-acylsphinganines (dihydroceramides)

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

• Molecular Weight: 566.000 g/mol
• XLogP3: 13.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 32
• Exact Mass: 565.543 Da
• Monoisotopic Mass: 565.543 Da
• Topological Polar Surface Area: 69.600 Ų
• Heavy Atom Count: 40
• Formal Charge: 0
• Complexity: 536.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1