(Z)-2-decenoic acid (cis-2-Decenoic acid) is an unsaturated fatty acid generated by Pseudomonas aeruginosa. (Z)-2-decenoic acid induces dispersion reactions in biofilms formed by a veriety of Gram-negative (Gram-) bacteria like Pseudomonas aeruginosa, and Gram-positive (Gram+) bacteria. (Z)-2-decenoic acid inhibits biofilm development.

Physicochemical Properties

Molecular Formula	C₁₀H₁₈O₂
Molecular Weight	170.25
Exact Mass	170.13
CAS #	15790-91-7
PubChem CID	5356596
Appearance	Colorless to light yellow liquid
Density	0.9±0.1 g/cm3
Boiling Point	278.6±9.0 °C at 760 mmHg
Flash Point	185.0±9.6 °C
Vapour Pressure	0.0±1.2 mmHg at 25°C
Index of Refraction	1.462
LogP	3.99
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	7
Heavy Atom Count	12
Complexity	139
Defined Atom Stereocenter Count	0
SMILES	CCCCCCC/C=C\C(O)=O
InChi Key	WXBXVVIUZANZAU-CMDGGOBGSA-N
InChi Code	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+
Chemical Name	(E)-dec-2-enoic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	(Z)-2-decenoic acid (cis-2-decenoic acid) stimulates the dispersion of biofilm microcolonies when given exogenously to Pseudomonas aeruginosa PAO1 biofilms at a native concentration of 2.5 nM [1]. (Z)-2-decenoic acid (also referred to as cis-2-decenoic acid) was identified as an extracellular signal molecule produced by Pseudomonas aeruginosa that induces dispersion of established biofilms and inhibits biofilm development. [1] Exogenously added (Z)-2-decenoic acid at its native concentration of 2.5 nM induced dispersion of P. aeruginosa PAO1 biofilm microcolonies in continuous culture flow cells. [1] In a microtiter plate dispersion bioassay, (Z)-2-decenoic acid showed dispersion-inducing activity against P. aeruginosa biofilms over a concentration range from 1.0 nM to 10 mM. [1] When added to 4-day-old P. aeruginosa biofilms grown in tube reactors, commercially synthesized (Z)-2-decenoic acid induced dispersion with an efficacy of 24.6% (±4.2%). [1] (Z)-2-decenoic acid also induced dispersion in biofilms formed by a range of other microorganisms including Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Streptococcus pyogenes, Bacillus subtilis, Staphylococcus aureus, and the yeast Candida albicans, demonstrating cross-species and cross-kingdom activity. [1]
Cell Assay	Microtiter Plate Dispersion Bioassay: Biofilms were grown on the inside surface of polystyrene microtiter plate wells pre-etched with acetone to enhance cell attachment. Cultures were grown in a semi-batch method with periodic medium replacement to reduce accumulation of endogenous dispersion factors. After 5-7 days of growth, biofilms were treated for 1 hour at 30°C with test samples (e.g., (Z)-2-decenoic acid dissolved in growth medium with 10% ethanol as a carrier) or sterile medium control. The medium containing dispersed cells was then transferred to a new plate, and cell density was measured by optical density at 570 nm (OD₅₇₀). [1] Biofilm Tube Reactor Assay: P. aeruginosa biofilms were grown in silicone tube reactors under continuous flow for 96 hours. For static treatment, a bolus of medium containing (Z)-2-decenoic acid was injected into the tubing, displacing the reactor volume. After 1 hour of exposure under non-flowing conditions, the liquid fraction containing released cells and the remaining biofilm fraction were collected separately. Cell numbers were determined by OD₆₀₀ measurement or viable plate counts. Dispersion efficacy was calculated as: (number of cells in bulk liquid / (number of cells in bulk liquid + number of cells in biofilm)) × 100%. [1]
References	[1]. A fatty acid messenger is responsible for inducing dispersion in microbial biofilms. J Bacteriol. 2009 Mar;191(5):1393-403.
Additional Infomation	Cis-2-decenoic acid is a 2-decenoic acid having its double bond in the cis configuration. (Z)-2-decenoic acid is an unsaturated fatty acid (C₁₀) with a cis-configuration double bond at the 2-position. [1] It is produced by P. aeruginosa during both batch and biofilm culture. [1] Its mechanism is proposed to be related to inducing a transition from biofilm to planktonic state, potentially as a response to overcrowding or starvation, allowing cells to relocate to more favorable environments. [1] The study hypothesizes that the dispersion response is activated when the inducer accumulates within a biofilm microcolony beyond a threshold concentration, which occurs when the microcolony size limits diffusive and advective washout of the signal. [1] The authors suggest that inducing biofilm dispersion with such signals prior to antimicrobial treatment could be a novel strategy to overcome biofilm resistance. [1]

Solubility Data

Solubility (In Vitro)

DMSO : ~250 mg/mL (~1468.43 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 6.25 mg/mL (36.71 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 62.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 6.25 mg/mL (36.71 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 62.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 6.25 mg/mL (36.71 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 62.5 mg/mL clear DMSO stock solution to 900 μL corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.8737 mL	29.3686 mL	58.7372 mL
	5 mM	1.1747 mL	5.8737 mL	11.7474 mL
	10 mM	0.5874 mL	2.9369 mL	5.8737 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.