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C14:1-DELTA9-CIS-(L)-HSL, also known as N-tetradecanoyl-L-homoserine lactone (C14-HSL), is a small diffusible signaling molecule that plays a crucial role in quorum sensing, a regulatory system used by bacteria to control gene expression in response to increasing cell density. It is involved in controlling gene expression and affecting cellular metabolism in bacteria, with its function primarily defined by the length of the acyl chain.

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  • 202284-87-5 Structure
  • Basic information

    1. Product Name: C14:1-DELTA9-CIS-(L)-HSL
    2. Synonyms: C14:1-DELTA9-CIS-(L)-HSL;C14-HSL;N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-TETRADECANAMIDE;N-tetradecanoyl-L-Homoserine lactone;C14-HSL, tDHL, N-Tetradecanoyl-L-hoMoserine lactone;Tetradecanoyl-L-hoMoserine lactone;N-[(3S)-2-oxooxolan-3-yl]tetradecanamide
    3. CAS NO:202284-87-5
    4. Molecular Formula: C18H33NO3
    5. Molecular Weight: 311.45952
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 202284-87-5.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 506.5±39.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 0.99±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: 14.70±0.20(Predicted)
    10. CAS DataBase Reference: C14:1-DELTA9-CIS-(L)-HSL(CAS DataBase Reference)
    11. NIST Chemistry Reference: C14:1-DELTA9-CIS-(L)-HSL(202284-87-5)
    12. EPA Substance Registry System: C14:1-DELTA9-CIS-(L)-HSL(202284-87-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 202284-87-5(Hazardous Substances Data)

202284-87-5 Usage

Uses

1. Used in Quorum Sensing Modulation:
C14:1-DELTA9-CIS-(L)-HSL is used as an active quorum sensing modulator for controlling bacterial communication and regulation. It helps in managing bacterial infections by quenching their quorum sensing systems, a promising field of study.
2. Used in Bacterial Gene Expression Control:
C14:1-DELTA9-CIS-(L)-HSL is used as a major modulator for cell communication, coordinating the expression of specific target genes, such as transcriptional regulators belonging to the LuxR family of proteins.
3. Used in Biofilm Development:
C14:1-DELTA9-CIS-(L)-HSL is used in the development of biofilms, as it appears later than shorter acyl chain AHLs and stimulates bacterial growth.
4. Used in Enhancing Bacterial Metabolism:
C14:1-DELTA9-CIS-(L)-HSL is used to alter the proteolytic activity and enhance the migration of some strains of Proteus mirabilis, affecting their cellular metabolism.
5. Used in Pharmaceutical Applications:
C14:1-DELTA9-CIS-(L)-HSL has potential applications in the pharmaceutical industry, particularly in the development of new drugs targeting bacterial infections by disrupting quorum sensing mechanisms.
6. Used in Research and Development:
C14:1-DELTA9-CIS-(L)-HSL is used as a research tool for studying the mechanisms of bacterial communication, gene expression, and biofilm development, contributing to the advancement of knowledge in microbiology and related fields.

Check Digit Verification of cas no

The CAS Registry Mumber 202284-87-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,2,2,8 and 4 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 202284-87:
(8*2)+(7*0)+(6*2)+(5*2)+(4*8)+(3*4)+(2*8)+(1*7)=105
105 % 10 = 5
So 202284-87-5 is a valid CAS Registry Number.

202284-87-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name N-tetradecanoyl-L-Homoserine lactone

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:202284-87-5 SDS

202284-87-5Downstream Products

202284-87-5Relevant articles and documents

Acyl-group specificity of AHL synthases involved in quorum-sensing in Roseobacter group bacteria

Ziesche, Lisa,Rinkel, Jan,Dickschat, Jeroen S.,Schulz, Stefan

supporting information, p. 1309 - 1316 (2018/06/13)

N-Acylhomoserine lactones (AHLs) are important bacterial messengers, mediating different bacterial traits by quorum sensing in a cell-density dependent manner. AHLs are also produced by many bacteria of the marine Roseobacter group, which constitutes a large group within the marine microbiome. Often, specific mixtures of AHLs differing in chain length and oxidation status are produced by bacteria, but how the biosynthetic enzymes, LuxI homologs, are selecting the correct acyl precursors is largely unknown. We have analyzed the AHL production in Dinoroseobacter shibae and three Phaeobacter inhibens strains, revealing strain-specific mixtures. Although large differences were present between the species, the fatty acid profiles, the pool for the acyl precursors for AHL biosynthesis, were very similar. To test the acyl-chain selectivity, the three enzymes LuxI1 and LuxI2 from D. shibae DFL-12 as well as PgaI2 from P. inhibens DSM 17395 were heterologously expressed in E. coli and the enzymes isolated for in vitro incubation experiments. The enzymes readily accepted shortened acyl coenzyme A analogs, N-pantothenoylcysteamine thioesters of fatty acids (PCEs). Fifteen PCEs were synthesized, varying in chain length from C4 to C20, the degree of unsaturation and also including unusual acid esters, e.g., 2E,11Z-C18:2-PCE. The latter served as a precursor of the major AHL of D. shibae DFL-12 LuxI1, 2E,11Z-C18:2-homoserine lactone (HSL). Incubation experiments revealed that PgaI2 accepts all substrates except C4 and C20-PCE. Competition experiments demonstrated a preference of this enzyme for C10 and C12 PCEs. In contrast, the LuxI enzymes of D. shibae are more selective. While 2E,11Z-C18:2-PCE is preferentially accepted by LuxI1, all other PCEs were not, except for the shorter, saturated C10-C14-PCEs. The AHL synthase LuxI2 accepted only C14 PCE and 3-hydroxydecanoyl-PCE. In summary, chain-length selectivity in AHLs can vary between different AHL enzymes. Both, a broad substrate acceptance and tuned specificity occur in the investigated enzymes.

Long-chain acyl-homoserine lactones from Methylobacterium mesophilicum: Synthesis and absolute configuration

Pomini, Armando M.,Cruz, Pedro L. R.,Gai, Claudia,Araujo, Welington L.,Marsaioli, Anita J.

supporting information; experimental part, p. 2125 - 2129 (2010/04/05)

The acyl-homoserine lactones (acyl-HSLs) produced by Methylobacterium mesophilicum isolated from orange trees infected with the citrus variegated chlorosis (CVC) disease have been studied, revealing the occurrence of six long-chain acyl-HSLs, i.e., the saturated homologues (S)-N-dodecanoyl (1) and (S)-N-tetradecanoyl-HSL (5), the uncommon odd-chain N-tridecanoyl-HSL (3), the new natural product (S)-N-(2E)-dodecenoyl-HSL (2), and the rare unsaturated homologues (S)-N-(7Z)-tetradecenoyl (4) and (S)-N-(2E,7Z)-tetradecadienyl-HSL (6). The absolute configurations of all HSLs were determined as 3S. Compounds 2 and 6 were synthesized for the first time. Antimicrobial assays with synthetic acyl-HSLs against Gram-positive bacterial endophytes co-isolated with M. mesophilicum from CVC-infected trees revealed low or no antibacterial activity.

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