8-Shogaol

CAS# 36700-45-5

8-Shogaol

Catalog No. BCN3266----Order now to get a substantial discount!

Product Name & Size Price Stock
8-Shogaol: 5mg $265 In Stock
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Chemical structure

8-Shogaol

3D structure

Chemical Properties of 8-Shogaol

Cas No. 36700-45-5 SDF Download SDF
PubChem ID 6442560 Appearance Colorless - yellowish viscous liquid
Formula C19H28O3 M.Wt 304.4
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in chloroform and methanol; insoluble in water
Chemical Name (E)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
SMILES CCCCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
Standard InChIKey LGZSMXJRMTYABD-MDZDMXLPSA-N
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 8-Shogaol

The rhizomes of Zingber officinale Rosc.

Biological Activity of 8-Shogaol

Description1. 8-Shogaol can induce apoptosis in a time- and concentration-dependent manner by reactive oxygen species production and depletion of glutathione in HL-60 cells.
TargetsROS

8-Shogaol Dilution Calculator

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8-Shogaol Molarity Calculator

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Preparing Stock Solutions of 8-Shogaol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.2852 mL 16.4258 mL 32.8515 mL 65.703 mL 82.1288 mL
5 mM 0.657 mL 3.2852 mL 6.5703 mL 13.1406 mL 16.4258 mL
10 mM 0.3285 mL 1.6426 mL 3.2852 mL 6.5703 mL 8.2129 mL
50 mM 0.0657 mL 0.3285 mL 0.657 mL 1.3141 mL 1.6426 mL
100 mM 0.0329 mL 0.1643 mL 0.3285 mL 0.657 mL 0.8213 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 8-Shogaol

Induction of apoptosis by [8]-shogaol via reactive oxygen species generation, glutathione depletion, and caspase activation in human leukemia cells.[Pubmed:20163181]

J Agric Food Chem. 2010 Mar 24;58(6):3847-54.

Ginger, the rhizome of Zingiber officinale , is a traditional medicine with a carminative effect and antinausea, anti-inflammatory, and anticarcinogenic properties. This study examined the growth inhibitory effects of [8]-shogaol, one of the pungent phenolic compounds in ginger, on human leukemia HL-60 cells. It demonstrated that [8]-shogaol was able to induce apoptosis in a time- and concentration-dependent manner. Treatment with [8]-shogaol caused a rapid loss of mitochondrial transmembrane potential, stimulation of reactive oxygen species (ROS) production, release of mitochondrial cytochrome c into cytosol, and subsequent induction of procaspase-9 and procaspase-3 processing. Taken together, these results suggest for the first time that ROS production and depletion of glutathione that contributed to [8]-shogaol-induced apoptosis in HL-60 cells.

Characterization of thiol-conjugated metabolites of ginger components shogaols in mouse and human urine and modulation of the glutathione levels in cancer cells by [6]-shogaol.[Pubmed:23322393]

Mol Nutr Food Res. 2013 Mar;57(3):447-58.

SCOPE: Shogaols, a series of major constituents in dried ginger with the most abundant being [6]-, [8]-, and [10]-shogaols, show much higher anticancer potencies than gingerols. Previously, we reported the mercapturic acid pathway as a major metabolic route for [6]-shogaol in mice. However, it is still unclear how the side chain length affects the metabolism of shogaols and how shogaols are metabolized in humans. METHODS AND RESULTS: We first investigate the metabolism of [10]-shogaol in mouse urine, and then investigate the biotransformation of shogaols in human urine. Our results show that eight major thiol-conjugated metabolites of [10]-shogaol were detected in mouse urine, while six major thiol-conjugated metabolites of [6]-shogaol, two thiol-conjugated metabolites of [8]-shogaol, and two thiol-conjugated metabolites of [10]-shogaol were detected in urine collected from human after drinking ginger tea, using LC/ESI-MS/MS. Our results clearly indicate the mercapturic acid pathway is a major metabolic route for [10]-shogaol in mice and for shogaols in human. Furthermore, we also investigated the regulation of glutathione (GSH) by [6]-shogaol in human colon cancer cells HCT-116. Our results show [6]-shogaol, after initially depleting glutathione levels, can subsequently restore and increase GSH levels over time. CONCLUSION: Shogaols are metabolized extensively in mouse and human to form thiol-conjugated metabolites and GSH might play an important role in the cancer-preventive activity of ginger.

Description

[8]-Shogaol, one of the pungent phenolic compounds in ginger, exhibits anti-platelet activity (IC50=5 μM) and inhibits COX-2 (IC50=17.5 μM). [8]-Shogaol induces apoptosis in human leukemia cells.

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