Date published: 2026-5-9

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cis-2-Dodecenoic acid (CAS 55928-65-9)

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Alternate Names:
BDSF; cis-2-lauroleic acid
Application:
cis-2-Dodecenoic acid is a diffusible fatty acid signal molecule
CAS Number:
55928-65-9
Molecular Weight:
198.30
Molecular Formula:
C12H22O2
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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cis-2-Dodecenoic acid, with the CAS number 55928-65-9, is an unsaturated fatty acid characterized by a double bond between the second and third carbon atoms in the cis configuration, and a total of twelve carbon atoms in its chain. This molecular structure imparts unique properties to the compound, particularly influencing its behavior in biological and chemical systems. The cis configuration introduces a bend in the molecule, altering its packing and interaction capabilities in lipid layers and interfaces. This acid has garnered attention in research focused on the study of biofilm dynamics and microbial communication. In the field of microbiology, cis-2-Dodecenoic acid is particularly noted for its role as a bacterial signaling molecule, involved in the process known as "quorum sensing." This process is critical for the regulation of gene expression based on the density of the microbial population. In practical applications, this compound has been explored for its potential to disrupt biofilm formation and maintenance, providing insights into the control of biofilm-associated problems in industrial and environmental settings. Additionally, the molecule′s unique structural features make it a useful tool in synthetic chemistry for the creation of complex organic compounds, serving as a precursor in various chemical syntheses aimed at producing materials with specific desired properties.


cis-2-Dodecenoic acid (CAS 55928-65-9) References

  1. Intraspecies signaling involving the diffusible signal factor BDSF (cis-2-dodecenoic acid) influences virulence in Burkholderia cenocepacia.  |  Ryan, RP., et al. 2009. J Bacteriol. 191: 5013-9. PMID: 19482924
  2. Blocking of Candida albicans biofilm formation by cis-2-dodecenoic acid and trans-2-dodecenoic acid.  |  Zhang, Y., et al. 2011. J Med Microbiol. 60: 1643-1650. PMID: 21778264
  3. Cis-2-dodecenoic acid receptor RpfR links quorum-sensing signal perception with regulation of virulence through cyclic dimeric guanosine monophosphate turnover.  |  Deng, Y., et al. 2012. Proc Natl Acad Sci U S A. 109: 15479-84. PMID: 22949660
  4. Cis-2-dodecenoic acid signal modulates virulence of Pseudomonas aeruginosa through interference with quorum sensing systems and T3SS.  |  Deng, Y., et al. 2013. BMC Microbiol. 13: 231. PMID: 24134835
  5. Burkholderia cenocepacia integrates cis-2-dodecenoic acid and cyclic dimeric guanosine monophosphate signals to control virulence.  |  Yang, C., et al. 2017. Proc Natl Acad Sci U S A. 114: 13006-13011. PMID: 29158389
  6. Protective Effects of cis-2-Dodecenoic Acid in an Experimental Mouse Model of Vaginal Candidiasis.  |  Yang, DL., et al. 2018. Biomed Environ Sci. 31: 816-828. PMID: 30558702
  7. Disruption of Quorum Sensing and Virulence in Burkholderia cenocepacia by a Structural Analogue of the cis-2-Dodecenoic Acid Signal.  |  Cui, C., et al. 2019. Appl Environ Microbiol. 85: PMID: 30770405
  8. Cis-2-dodecenoic Acid Mediates Its Synergistic Effect with Triazoles by Interfering with Efflux Pumps in Fluconazole-resistant Candida albicans.  |  Yang, DL., et al. 2019. Biomed Environ Sci. 32: 199-209. PMID: 30987694
  9. Candida albicans Ubiquitin and Heat Shock Factor-Type Transcriptional Factors Are Involved in 2-Dodecenoic Acid-Mediated Inhibition of Hyphal Growth.  |  Yang, D., et al. 2020. Microorganisms. 8: PMID: 31947778
  10. The cis-2-Dodecenoic Acid (BDSF) Quorum Sensing System in Burkholderia cenocepacia.  |  Wang, M., et al. 2022. Appl Environ Microbiol. 88: e0234221. PMID: 34985987

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

cis-2-Dodecenoic acid, 10 mg

sc-396647
10 mg
$225.00