الصفحة الرئيسية>>Analytical Standards>>(±)12(13)-DiHOME

(±)12(13)-DiHOME (Synonyms: Isoleukotoxin diol)

رقم الكتالوجGC40802

(±)12(13)-DiHOME is the diol form of (±)12(13)-EpOME, a cytochrome P450-derived epoxide of linoleic acid also known as isoleukotoxin.

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(±)12(13)-DiHOME التركيب الكيميائي

Cas No.: 263399-35-5

الحجم السعر المخزون الكميّة
25μg
43٫00
متوفر
50μg
82٫00
متوفر
100μg
155٫00
متوفر
500μg
686٫00
متوفر

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Sample solution is provided at 25 µL, 10mM.

Description of (±)12(13)-DiHOME

(±)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. Levels are also elevated in bronchoalveolar lavage fluid (BALF) in humans following exposure to biodiesel exhaust and in exhaled breath condensate in patients with allergic 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]

Reference:
[1]. Greene, J.F., Williamson, K.C., Newman, J.W., et al. Metabolism of monoepoxides of methyl linoleate: Bioactivation and detoxification. Arch. 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 hydrolase. Nat. 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 injury. Mol. Pain 12, (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 tissue. Nat. 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 exposure. Anal. 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 spectrometry. IEEE 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 uptake. Cell Metab. 27(5), 1111-1120 (2018).

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

Cas No. 263399-35-5 SDF
المرادفات Isoleukotoxin diol
Chemical Name 12,13-dihydroxy-9Z-octadecenoic acid
Canonical SMILES CCCCC[C@@H](O)[C@@H](O)C/C=C\CCCCCCCC(O)=O
Formula C18H34O4 M.Wt 314.5
الذوبان DMF: 20 mg/ml,DMSO: 20 mg/ml,Ethanol: 20 mg/ml,PBS (pH 7.2): 10 µ g/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

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 3.1797 mL 15.8983 mL 31.7965 mL
5 mM 0.6359 mL 3.1797 mL 6.3593 mL
10 mM 0.318 mL 1.5898 mL 3.1797 mL
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Product Documents

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