N-stearoyl-D-erythro-sphingosine - ≥99% , CAS No.2304-81-6

CAS: 2304-81-6 Cat. No.: N130622 Molecular Weight: 565.954 Beilstein Registry Number: 1717539

GRADE & PURITY ≥99%

Synonyms

C18 Ceramide (d18:1/18:0) | N-(octadecanoyl)ceramide | N-(octadecanoyl)-ceramide | octadecanamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]- | CHEBI:72961 | J-014959 | N-Stearoylsphingosine | C18 Ceramide | AS-75860 | C18 Ceramide (d18:1/

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

C18 Ceramide (d18:1/18:0) synthesis is catalyzed by ceramide synthase (CERS) 1 and 5. It is a component of cellular membrane and has low gel forming ability compared to unsaturated ceramide

C18 Ceramide (d18:1/18:0) has been used:

· to induce apoptosis in Manduca embryonic cell line (MRRL-CH1)

· as a standard to quantify ceramide from liver tissue using liquid chromatography-mass spectrometry

· to inhibit ceramidase in human embryonic kidney cells (HEK29) with β-glucocerebrosidase (GCase) mutation

Specifications

Synonyms

C18 Ceramide (d18:1/18:0) | N-(octadecanoyl)ceramide | N-(octadecanoyl)-ceramide | octadecanamide, N-[(1S, 2R, 3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]- | CHEBI:72961 | J-014959 | N-Stearoylsphingosine | C18 Ceramide | AS-75860 | C18 Ceramide (d18:1/

Specifications & Purity

≥99%

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

• Pubchem Sid: 504763469
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763469
• Canonical Smiles: CCCCCCCCCCCCCCCCCC(=O)NC(CO)C(C=CCCCCCCCCCCCCC)O
• IUPAC Name: N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octadecanamide
• InChIKey: VODZWWMEJITOND-NXCSZAMKSA-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/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)/b31-29+/t34-,35+/m0/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O
• Molecular Weight: 565.954
• Beilstein: 1717539
• Reaxy-Rn: 27424623
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=27424623&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-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 chloroform. Insoluble in water.
• Molecular Weight: 566.000 g/mol
• XLogP3: 13.900
• 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

References

1. Jie Zhang, Xiaoling Zang, Wei Meng, Peng Jiao, Jiangyu Wu, Lizhen Zhao, Zhuangzhuang Li, Xin Zhang, Huanhuan Yang, Zhihua Lv.  (2025)  Altered levels of sphingomyelins, ceramides, glycerophospholipids, and diacylglycerols in thymoma tissues.  BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR AND CELL BIOLOGY OF LIPIDS,      [PMID:40553894] [10.1016/j.bbalip.2025.159650]