6-Shogaol

6-Shogaol, a naturally occuring product found in ginger, has anti-inflammatory and anticancer properties.

Product information

CAS Number: 555-66-8

Molecular Weight: 276.37

Formula: C17H24O3

Synonym:

[6]-Shogaol

6-Shogaol

Chemical Name: 1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one

Smiles: CCCCCC=CC(=O)CCC1C=CC(O)=C(C=1)OC

InChiKey: OQWKEEOHDMUXEO-BQYQJAHWSA-N

InChi: InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : ≥ 50 mg/mL (180.92 mM)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Shogaol ([6]-Shogaol) has anticancer activity against several cell lines. Shogaol ([6]-Shogaol) is identified to be cytotoxic in various cell lines, with KB (IC50=7.4±2.2 μM) and HL60 (IC50=7.9±2.0 μM) cells most susceptible to 6-shogaol. 6-shogaol (IC50=8 μM) has much stronger growth inhibitory effects than 6-gingerol (IC50=150 μM) on HCT-116 human colon cancer cells. Shogaol ([6]-Shogaol) stimulates phosphorylations of mitogen-activated protein kinases (MAPKs) such as ERK, JNK, and p38. Moreover, the 6-shogaol-induced expressions of Nrf2 and HO-1 are attenuated by treatments of SB202190 (a p38 specific inhibitor) and LY294002 (an Akt specific inhibitor).

In Vivo:

The Shogaol ([6]-Shogaol) decreases the diethylnitrosamine (DEN)-mediated elevations of serum aspartate transaminase and alanine transaminase as well as the DEN-induced hepatic lipid peroxidation. Inductions of Nrf2 and HO-1 by 6-shogaol are also confirmed in the mice. The administration of Shogaol ([6]-Shogaol) to the mice also restores the DEN-reduced activity and protein expression of hepatic antioxidant enzymes such as superoxide dismutase, glutathione peroxidase and catalase.

References:

1. Semwal RB, et al. Gingerols and shogaols: Important nutraceutical principles from ginger. Phytochemistry. 2015 Sep;117:554-68.
2. Peng F, et al. Cytotoxic, cytoprotective and antioxidant effects of isolated phenolic compounds from fresh ginger. Fitoterapia. 2012 Apr;83(3):568-85.
3. Sang S, et al. Increased growth inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols from Zingiber officinale relative to gingerols. J Agric Food Chem. 2009 Nov 25;57(22):10645-50.
4. Bak MJ, et al. 6-shogaol-rich extract from ginger up-regulated the antioxidant defense systems in cells and mice. Molecules. 2012 Jul 4;17(7):8037-55.

Products are for research use only. Not for human use.