cis-2-Decenoic acid
Names
Preferred IUPAC name
(2Z)-Dec-2-enoic acid
Identifiers
3D model (JSmol)
1721990
ChEBI
ChemSpider
ECHA InfoCard 100.229.919
EC Number
  • 223-475-8
  • InChI=1S/C10H18O2/c1-2-3-4-5-6-7-8-9-10(11)12/h8-9H,2-7H2,1H3,(H,11,12)/b9-8-
    Key: WXBXVVIUZANZAU-HJWRWDBZSA-N
  • O=C(O)\C=C/CCCCCCC
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 labelling:
GHS07: Exclamation mark
Warning
H315, H319
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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. PMC 2648214. 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. PMC 4695811. PMID 26610524.
  4. ↑ Bryers, JD (2008). "Medical biofilms". Biotechnol. Bioeng. 100 (1): 1–18. doi:10.1002/bit.21838. PMC 2706312. PMID 18366134.


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