>>Lipids>> P450>>(±)12(13)-DiHOME-d4

(±)12(13)-DiHOME-d4 (Synonyms: Isoleukotoxin diold4)

Catalog No.GC46256

A neuropeptide with diverse biological activities

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(±)12(13)-DiHOME-d4 Chemical Structure

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25 μg
US$128.00
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50 μg
US$245.00
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100 μg
US$462.00
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250 μg
US$1,028.00
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Sample solution is provided at 25 µL, 10mM.

Description of (±)12(13)-DiHOME-d4

(±)12(13)-DiHOME-d4 is intended for use as an internal standard for the quantification of (±)12(13)-DiHOME by GC- or LC-MS. (±)12(13)-DiHOME is the diol form of (±)12(13)-EpOME, a cytochrome P450-derived epoxide of linoleic acid also known as isoleukotoxin.1 It is formed from 12(13)-EpOME by soluble epoxide hydrolase (sEH) in neutrophils.2 12(13)-DiHOME is toxic to Sf21 cells expressing sEH and to lacZ-expressing control cells, unlike isoleukotoxin, which is only toxic to cells containing sEH.1,2 Levels of 12(13)-DiHOME are increased in rat spinal cord following burn injury, and it enhances cold tolerance, increases fatty acid uptake into brown adipocytes, and decreases serum triglyceride levels in mice.3,4 Levels are also elevated in bronchoalveolar lavage fluid (BALF) in humans following exposure to biodiesel exhaust and in exhaled breath condensate in patients with asthma following allergen exposure.5,6 Plasma levels of 12(13)-DiHOME are increased immediately following moderate-intensity exercise in mice and humans, an effect that can be prevented by brown adipose tissue removal in the mouse.7

1.Greene, J.F., Williamson, K.C., Newman, J.W., et al.Metabolism of monoepoxides of methyl linoleate: Bioactivation and detoxificationArch. Biochem. Biophys.376(2)420-432(2000) 2.Moghaddam, M.F., Grant, D.F., Cheek, J.M., et al.Bioactivation of leukotoxins to their toxic diols by epoxide hydrolaseNat. Med.3(5)562-566(1997) 3.Green, D.P., Ruparel, S., Gao, X., et al.Central activation of TRPV1 and TRPA1 by novel endogenous agonists contributes to mechanical allodynia and thermal hyperalgesia after burn injuryMol. Pain12(2016) 4.Lynes, M.D., Leiria, L.O., Lundh, M., et al.The cold-induced lipokine 12,13-diHOME promotes fatty acid transport into brown adipose tissueNat. Med.23(5)631-637(2017) 5.Gouveia-Figueira, S., Karimpour, M., Bosson, J.A., et al.Mass spectrometry profiling of oxylipins, endocannabinoids, and N-acylethanolamines in human lung lavage fluids reveals responsiveness of prostaglandin E2 and associated lipid metabolites to biodiesel exhaust exposureAnal. Bioanal. Chem.409(11)2967-2980(2017) 6.Nording, M.L., Yang, J., Hegedus, C.M., et al.Endogenous levels of five fatty acid metabolites in exhaled breath condensate to monitor asthma by high-performance liquid chromatography: Electrospray tandem mass spectrometryIEEE Sens. J.10(1)123-130(2010) 7.Stanford, K.I., Lynes, M.D., Takahashi, H., et al.12,13-diHOME: An exercise-induced lipokine that increases skeletal muscle fatty acid uptakeCell Metab.27(5)1111-1120(2018)

Chemical Properties of (±)12(13)-DiHOME-d4

Cas No. N/A SDF
Synonyms Isoleukotoxin diold4
Canonical SMILES CCCCC[C@](O)([2H])[C@](O)([2H])C/C([2H])=C([2H])\CCCCCCCC(O)=O
Formula C18H30D4O4 M.Wt 318.5
Solubility DMF: 20 mg/ml,DMSO: 20 mg/ml,Ethanol: 20 mg/ml,PBS (pH 7.2): 10 μg/ml Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of (±)12(13)-DiHOME-d4

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1 mg 5 mg 10 mg
1 mM 3.1397 mL 15.6986 mL 31.3972 mL
5 mM 0.6279 mL 3.1397 mL 6.2794 mL
10 mM 0.314 mL 1.5699 mL 3.1397 mL
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