Chemistry:Cis-2-Decenoic acid

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cis-2-Decenoic acid
Cis-2-decenoic acid.svg
Names
Preferred IUPAC name
(2Z)-Dec-2-enoic acid
Identifiers
3D model (JSmol)
1721990
ChEBI
ChemSpider
EC Number
  • 223-475-8
Properties
C10H18O2
Molar mass 170.252 g·mol−1
Boiling point 102–103 °C (216–217 °F; 375–376 K) at 0.5 mmHg
Hazards
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319
P264, P280, P302+352, P305+351+338, P321, P332+313, P337+313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

cis-2-Decenoic acid is an unsaturated fatty acid. It is a colorless oil.

Preparation and occurrence

The compound can be prepared from 1-iodonon-1-ene by lithium halogen exchange followed by carbonation.[1]

cis-2-Decenoic acid is produced by Pseudomonas aeruginosa.[2] It may have potential in fighting biofilm implied in infectious diseases[3] that are present in more than 60%[4] of Hospital-acquired infection.

References

  1. Cahiez, G.; Bernard, D.; Normant, J. F. (1976). "Stereospecific Syntheses of Alkenyllithium Reagents from Alkenyl Iodides". Synthesis 1976 (4): 245–248. doi:10.1055/s-1976-25384. 
  2. Davies, DG; Marques, CN (2009). "A fatty acid messenger is responsible for inducing dispersion in microbial biofilms". Journal of Bacteriology 191 (5): 1393–403. doi:10.1128/JB.01214-08. PMID 19074399. 
  3. Marques, CN; Davies, DG; Sauer, K (2015). "Control of Biofilms with the Fatty Acid Signaling Molecule cis-2-Decenoic Acid". Pharmaceuticals 8 (4): 816–35. doi:10.3390/ph8040816. PMID 26610524. 
  4. Bryers, JD (2008). "Medical biofilms". Biotechnol. Bioeng. 100 (1): 1–18. doi:10.1002/bit.21838. PMID 18366134.