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

CAS: 67492-16-4 Cat. No.: N130621 Peso molecular: 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

Conservar a -20°C

Shipped In

Hielera + almohadillas de hielo

Descripción general

La síntesis de ceramidas se realiza bien por la vía de recuperación mediante la acilación de la esfingosina o la hidrólisis de esfingolípidos, bien por la vía de novo mediante la formación de dihidroceramidas. Estructuralmente, las ceramidas tienen una base esfingoide, un aminoalcohol de cadena larga unido a un ácido graso por un enlace amida.

Aplicación：

La ceramida C17 (d18:1/17:0) se ha utilizado
como patrón interno para la cuantificación de ceramida miocárdica mediante cromatografía con ionización por electrospray de iones negativos acoplada a espectrometría de masas en tándem；como patrón interno en espectrometría de masas en tándem (MS/MS)；como sustrato para la enzima esfingomielina sintasa 2

Specifications

Sinónimos

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

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

Las ceramidas desempeñan un papel clave en la regulación de diversos procesos celulares, como la senescencia y la apoptosis, participan directamente en la proliferación y diferenciación de las células cutáneas y regulan la funcionalidad de la barrera cutá

Condiciones de almacenamiento de almacenamiento

Conservar a -20°C

Enviado en

Hielera + almohadillas de hielo

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: 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
• Isómeros SMILES: CCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O
• Peso molecular: 551.93

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: 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
• Descripción: 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

Objetivos asociados (no humanos)

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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Mecanismos de acción

Propiedades químicas y físicas

• Peso molecular: 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

Referencias

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]