Cis-2-Decenoic acid

*cis*-2-Decenoic acid
Names
	Preferred IUPAC name (2Z)-Dec-2-enoic acid
Identifiers
CAS Number	15790-91-7 ;
3D model (JSmol)	Interactive image ;
Beilstein Reference	1721990
ChEBI	CHEBI:50466 ;
ChemSpider	4512229 ;
ECHA InfoCard	100.229.919
EC Number	223-475-8;
PubChem CID	5356596 ;
CompTox Dashboard (EPA)	DTXSID40418140 ;
	InChI 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;
	SMILES O=C(O)\C=C/CCCCCCC;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	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

Last updated June 08, 2025

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

↑ 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. S2CID 95870283.
↑ 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.
↑ 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.
↑ Bryers, JD (2008). "Medical biofilms". Biotechnol. Bioeng. 100 (1): 1–18. doi:10.1002/bit.21838. PMC 2706312 . PMID 18366134.

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[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. S2CID 95870283.

[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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Names

Preferred IUPAC name (2Z)-Dec-2-enoic acid
Identifiers
CAS Number	15790-91-7
3D model (JSmol)	Interactive image
Beilstein Reference	1721990
ChEBI	CHEBI:50466
ChemSpider	4512229
ECHA InfoCard	100.229.919
EC Number	223-475-8
PubChem CID	5356596
CompTox Dashboard (EPA)	DTXSID40418140
InChI 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
SMILES O=C(O)\C=C/CCCCCCC
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	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