(±)8(9)-EpETE ((±)8,9-EEQ; (±)8,9-epoxy Eicosatetraenoic acid) can be converted to epoxyeicosatetraenoic acid (EpETE) by multiple cytochrome P450 isozymes. The major product of the epoxide pathway is (±)17(18)-EpETE, which directly interacts with BKα channel subunits to activate large conductance Ca2+-activated K+ (BKCa) channels, thereby relaxing vascular and airway smooth muscle. (±)8(9)-EpETE is an epoxide pathway product that is generated from EPA by CYP450 both in vitro and in vivo.

Physicochemical Properties

Molecular Formula	C20H30O3
Molecular Weight	318.45
Exact Mass	318.219
CAS #	851378-93-3
PubChem CID	16061086
Appearance	Typically exists as solid at room temperature
Density	1.0±0.1 g/cm3
Boiling Point	460.2±30.0 °C at 760 mmHg
Flash Point	154.9±18.1 °C
Vapour Pressure	0.0±2.4 mmHg at 25°C
Index of Refraction	1.513
LogP	5.62
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	13
Heavy Atom Count	23
Complexity	432
Defined Atom Stereocenter Count	0
SMILES	CC/C=C\C/C=C\C/C=C\CC1C(O1)C/C=C\CCCC(=O)O
InChi Key	YKIOHMXLFWMWKD-JJUYGIQRSA-N
InChi Code	InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h3-4,6-7,9-10,12-13,18-19H,2,5,8,11,14-17H2,1H3,(H,21,22)/b4-3-,7-6-,12-9-,13-10-
Chemical Name	(Z)-7-[3-[(2Z,5Z,8Z)-undeca-2,5,8-trienyl]oxiran-2-yl]hept-5-enoic acid
Synonyms	(±)8,9-EEQ; (±)8,9-epoxy Eicosatetraenoic 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

References	[1]. Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activators. Hypertension 39(2 Pt. 2), 609-613 (2002).
Additional Infomation	(5Z,11Z,14Z,17Z)-8,9-epoxyicosatetraenoic acid is an EpETE obtained by formal epoxidation of the 8,9-double bond of all-cis-5,8,11,14,17-icosapentaenoic acid. It is functionally related to an all-cis-5,8,11,14,17-icosapentaenoic acid. It is a conjugate acid of a (5Z,11Z,14Z,17Z)-8,9-epoxyicosatetraenoate.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.1402 mL	15.7011 mL	31.4021 mL
	5 mM	0.6280 mL	3.1402 mL	6.2804 mL
	10 mM	0.3140 mL	1.5701 mL	3.1402 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.