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8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate

CAS# 67667-71-4

8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate

Catalog No. BCN7107----Order now to get a substantial discount!

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8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate: 5mg $690 In Stock
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Quality Control of 8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate

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Chemical structure

8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate

3D structure

Chemical Properties of 8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate

Cas No. 67667-71-4 SDF Download SDF
PubChem ID 70686496 Appearance Powder
Formula C21H26O8 M.Wt 406.43
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1R,2E,8S,10R,11S)-6-(acetyloxymethyl)-11-hydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradeca-2,6-dien-8-yl] 2-methylprop-2-enoate
SMILES CC1CC(C2=C(C(=O)OC2=CC3(CCC1(O3)O)C)COC(=O)C)OC(=O)C(=C)C
Standard InChIKey YKIDGUZXBGGNBZ-GUNZAYKBSA-N
Standard InChI InChI=1S/C21H26O8/c1-11(2)18(23)27-15-8-12(3)21(25)7-6-20(5,29-21)9-16-17(15)14(19(24)28-16)10-26-13(4)22/h9,12,15,25H,1,6-8,10H2,2-5H3/b16-9+/t12-,15+,20-,21+/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate

The herbs of Vernonia cinerea.

Biological Activity of 8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate

Description1. 8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate shows inhibitory activity toward CYP2A6 and MAO-A and MAO-B enzymes.
TargetsP450 (e.g. CYP17) | MAO | NADPH-oxidase

8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate Dilution Calculator

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8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate Molarity Calculator

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Preparing Stock Solutions of 8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4604 mL 12.3022 mL 24.6045 mL 49.209 mL 61.5112 mL
5 mM 0.4921 mL 2.4604 mL 4.9209 mL 9.8418 mL 12.3022 mL
10 mM 0.246 mL 1.2302 mL 2.4604 mL 4.9209 mL 6.1511 mL
50 mM 0.0492 mL 0.246 mL 0.4921 mL 0.9842 mL 1.2302 mL
100 mM 0.0246 mL 0.123 mL 0.246 mL 0.4921 mL 0.6151 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate

Inhibition effects of Vernonia cinerea active compounds against cytochrome P450 2A6 and human monoamine oxidases, possible targets for reduction of tobacco dependence.[Pubmed:25857233]

Drug Metab Pharmacokinet. 2015 Apr;30(2):174-81.

The human cytochrome P450 2A6 (CYP2A6) and monoamine oxidases (MAO-A and MAO-B), catalyzing nicotine and dopamine metabolisms, respectively, are two therapeutic targets of nicotine dependence. Vernonia cinerea, a medicinal plant commonly used for treatment of diseases such as asthma and bronchitis, has been shown reducing tobacco dependence effect among tobacco users. In the present study, we found eight active compounds isolated from V. cinerea that comprise inhibitory activity toward CYP2A6 and MAO-A and MAO-B enzymes using activity-guided assays, with coumarin as substrate of CYP2A6 and kynuramine of MAOs. These compounds were three flavones (apigenin, chrysoeriol, luteolin), one flavonol (quercetin), and four hirsutinolide-type sesquiterpene lactones (8alpha-(2-methylacryloyloxy)-hirsutinolide-13-O-acetate, 8alpha-(4-hydroxymethacryloyloxy)-hirsutinolide-13-O-acetate, 8alpha-tigloyloxyhirsutinolide-13-O-acetate, and 8alpha-(4-hydroxytigloyloxy)-hirsutinolide-13-O-acetate). Modes and kinetics of inhibition against the three enzymes were determined. Flavonoids possessed strong inhibitory effect on CYP2A6 in reversible mode, while inhibition by hirsutinolides was mechanism-based (NADPH-, concentration-, and time-dependence) and irreversible. Inhibition by hirsutinolides could not be reversed by dialysis and by addition of trapping agents or potassium ferricyanide. Flavonoids inhibited MAOs with variable degrees and were more prominent in inhibition toward MAO-A than hirsutinolides, while two of hirsutinolides inhibited MAO-B approximately comparable to two flavonoids. These results could have implications in combination of drug therapy for smoking cessation.

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