677354-23-3

Basic information

• Product Name: cis-Δ2-11-methyl-Dodecenoic Acid
• Synonyms: Diffusible signal factor;(2Z)-11-Methyl-2-dodecenoic acid;cis-Δ2-11-methyl-Dodecenoic Acid;cis-11-Methyl-2-dodecenoic acid;(Z)-11-Methyldodec-2-enoic acid;Cis-11-Methyl-2-dodecenoic acid, DSF;cis-.DELTA.2-11-methyl-Dodecenoic Acid
• CAS NO: 677354-23-3
• Molecular Formula: C13H24O2
• Molecular Weight: 212.32846
• Mol File: 677354-23-3.mol

Chemical Properties

• Boiling Point: 322.28 °C at 760 mmHg
• Flash Point: 226.505 °C
• Appearance: /
• Density: 0.916 g/cm³
• Storage Temp.: ?20°C
• PKA: 4.61±0.25(Predicted)
• CAS DataBase Reference: cis-Δ2-11-methyl-Dodecenoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: cis-Δ2-11-methyl-Dodecenoic Acid(677354-23-3)
• EPA Substance Registry System: cis-Δ2-11-methyl-Dodecenoic Acid(677354-23-3)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/38-51/53
• Safety Statements: 26-61
• RIDADR: UN 3082 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 677354-23-3(Hazardous Substances Data)

Usage

Uses

Used in Microbiology Research:
cis-Δ2-11-methyl-Dodecenoic Acid is used as a signaling molecule for studying cell-cell communication in pathogenic bacteria such as Xanthomonas campestris pv. Campestris (Xcc). It plays a vital role in the synchronization of virulence gene expression and biofilm dispersal, providing valuable insights into the mechanisms of bacterial pathogenicity and potential targets for antimicrobial therapies.
Used in Fungal Pathogen Studies:
cis-Δ2-11-methyl-Dodecenoic Acid is used as a virulence regulator in studies involving Candida albicans, a fungal pathogen. Its structural and functional relationship to farnesoic acid (FA) makes it an important compound for understanding the regulation of morphological transition and virulence in this organism, which can contribute to the development of novel antifungal treatments.
Used in Plant Pathogen Research:
cis-Δ2-11-methyl-Dodecenoic Acid is used as a virulence regulator in Xanthomonas campestris pv. campestris, a plant pathogenic bacterium. It helps in understanding the molecular mechanisms underlying bacterial pathogenicity and the development of strategies to control plant diseases caused by this bacterium.

InChI:InChI=1S/C13H24O2/c1-12(2)10-8-6-4-3-5-7-9-11-13(14)15/h9,11-12H,3-8,10H2,1-2H3,(H,14,15)/b11-9-

Upstream product

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Relevant articles and documents

ANTI-BACTERIAL CALCIUM-DEPENDENT ANTIBIOTIC (CDA) ANALOGS AND METHODS OF TREATING BACTERIAL INFECTIONS

Provided herein are calcium-dependent antibiotics (CDAs), as a novel therapeutic target for treating bacterial infections. The present invention also relates to pharmaceutical compositions comprising such compounds, and to methods of use thereof for combating bacteria and treating bacterial infections.

Modulation of antibiotic sensitivity and biofilm formation in Pseudomonas aeruginosa by interspecies signal analogues

Pseudomonas aeruginosa, a significant opportunistic pathogen, can participate in inter-species communication through signaling by cis-2-unsaturated fatty acids of the diffusible signal factor (DSF) family. Sensing these signals leads to altered biofilm formation and increased tolerance to various antibiotics, and requires the histidine kinase PA1396. Here, we show that the membrane-associated sensory input domain of PA1396 has five transmembrane helices, two of which are required for DSF sensing. DSF binding is associated with enhanced auto-phosphorylation of PA1396 incorporated into liposomes. Further, we examined the ability of synthetic DSF analogues to modulate or inhibit PA1396 activity. Several of these analogues block the ability of DSF to trigger auto-phosphorylation and gene expression, whereas others act as inverse agonists reducing biofilm formation and antibiotic tolerance, both in vitro and in murine infection models. These analogues may thus represent lead compounds to develop novel adjuvants improving the efficacy of existing antibiotics.

Synthesis of the quorum sensing molecule Diffusible Signal Factor using the alkyne zipper reaction

The development of a concise synthesis of the quorum sensing molecule Diffusible Signal Factor is described. This route exploits an alkyne zipper reaction to form a key terminal alkyne intermediate. The chemistry outlined here may also be applied to the preparation of cis-unsaturated analogues of Diffusible Signal Factor.

INHIBITORS OF YEAST FILAMENTOUS GROWTH AND METHOD OF THEIR MANUFACTURE

The invention broadly relates to the use of α, β-unsaturated fatty acids to inhibit the filamentous growth of fungi and yeasts and to a method for producing same. In particular the invention relates to the use of optionally substituted C8 to C15 α, β-unsaturated fatty acids or salts, esters or amides thereof for inhibiting or retarding the yeast-to-mycelium transition of organisms having a dimorphic life cycle.