N-hexadecanoyl-L-Homoserine lactone - ≥98% , CAS No.87206-01-7

CAS: 87206-01-7 Cat. No.: N347384 Molecular Weight: 339.5

GRADE & PURITY ≥98%

Synonyms

N-palmitoyl-L-Homoserine | N-hexadecanoyl-L-Homoserine lactone | C16-HSL | (S)-N-(2-oxotetrahydrofuran-3-yl)palmitamide

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

N-hexadecanoyl-L-Homoserine lactone is one of a number of lipophilic, long acyl side-chain bearing AHLs produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in|S. meliloti|, a nitrogen-fixing bacteria. It is the most abundant AHL produced by the proteobacterium|R. capsulatus|and activates genetic exchange between|R. capsulatus|cells. N-hexadecanoyl-L-Homoserine lactone tends to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by extracellular outer membrane vesicles.

Specifications

Synonyms

N-palmitoyl-L-Homoserine | N-hexadecanoyl-L-Homoserine lactone | C16-HSL | (S)-N-(2-oxotetrahydrofuran-3-yl)palmitamide

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

• Pubchem Sid: 488197621
• Canonical Smiles: CCCCCCCCCCCCCCCC(=O)NC1CCOC1=O
• IUPAC Name: N-[(3S)-2-oxooxolan-3-yl]hexadecanamide
• InChIKey: QJIXVOQAEZMUIH-SFHVURJKSA-N
• INCHI: 1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)21-18-16-17-24-20(18)23/h18H,2-17H2,1H3,(H,21,22)/t18-/m0/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
• Molecular Weight: 339.5
• Reaxy-Rn: 1652503
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1652503&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 N-acyl-alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: N-acyl-alpha amino acids and derivatives
• Alternative Parents: Alpha amino acid esters Acyl-L-homoserine lactones N-acyl amines Gamma butyrolactones Oxolanes Secondary carboxylic acid amides Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Alpha-amino acid ester - N-acyl-alpha amino acid or derivatives - Acyl-homoserine lactone - Acyl-l-homoserine lactone - Fatty amide - Gamma butyrolactone - N-acyl-amine - Fatty acyl - Oxolane - Carboxamide group - Carboxylic acid ester - Lactone - Secondary carboxylic acid amide - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organic oxide - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
• External Descriptors: Not available

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: 339.500 g/mol
• XLogP3: 7.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 339.277 Da
• Monoisotopic Mass: 339.277 Da
• Topological Polar Surface Area: 55.400 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 344.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1