C17 Ceramide (d18:1/17:0) - ≥98% , CAS No.67492-16-4

CAS: 67492-16-4 Cat. No.: N130621 Molecular Weight: 551.93

GRADE & PURITY ≥98%

Synonyms

N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]heptadecanamide | N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]heptadecanamide | C17 Ceramide (d18:1/17:0), N-heptadecanoyl-D-erythro-sphingosine, powder | N-Heptadecanoylsphingosine | n-heptadecanoyl-sphingosin

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Ceramide synthesis is mediated either by the salvage pathway by the acylation of sphingosine or sphingolipids hydrolysis or by de novo pathway via dihydroceramide formation. Structurally, ceramides have a sphingoid base, a long-chain amino alcohol linked to fatty acid by an amide bond.

Application：

C17 Ceramide (d18:1/17:0) has been used:
as an internal standard for myocardial ceramide quantification using chromatography with negative ion electrospray ionization coupled to tandem mass spectrometry；as an internal standard in tandem mass spectrometry (MS/MS)；as a substrate for sphingomyelin synthase 2 enzyme

Specifications

Synonyms

N-[(2S, 3R, 4E)-1, 3-dihydroxyoctadec-4-en-2-yl]heptadecanamide | N-[(E, 2S, 3R)-1, 3-dihydroxyoctadec-4-en-2-yl]heptadecanamide | C17 Ceramide (d18:1/17:0), N-heptadecanoyl-D-erythro-sphingosine, powder | N-Heptadecanoylsphingosine | n-heptadecanoyl-sphingosin

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Ceramides play a key role in regulating various cellular processes like senescence and apoptosis.They are directly involved in the proliferation and differentiation of skin cells and regulate skin barrier functionality.Ceramide based analogs are potential

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: CCCCCCCCCCCCCCCCC(=O)NC(CO)C(C=CCCCCCCCCCCCCC)O
• IUPAC Name: N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]heptadecanamide
• InChIKey: ICWGMOFDULMCFL-QKSCFGQVSA-N
• INCHI: 1S/C35H69NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-35(39)36-33(32-37)34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h28,30,33-34,37-38H,3-27,29,31-32H2,1-2H3,(H,36,39)/b30-28+/t33-,34+/m0/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O
• Molecular Weight: 551.93

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

Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)

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Proteus vulgaris (5823 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Bacillus pumilus (984 Activities)

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Aspergillus niger (16508 Activities)

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Bacillus subtilis (32866 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 551.900 g/mol
• XLogP3: 13.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 31
• Exact Mass: 551.528 Da
• Monoisotopic Mass: 551.528 Da
• Topological Polar Surface Area: 69.600 Ų
• Heavy Atom Count: 39
• Formal Charge: 0
• Complexity: 522.000
• 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]