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345868

Sigma-Aldrich

[6]-Gingerol, Zingiber officinale - CAS 23513-14-6 - Calbiochem

An antitumor, apoptosis-inducing compound of the ginger family that blocks EGF-induced cell transformation by inhibiting the activation of Activator Protein-1 (AP-1).

Synonym(s):
1-(4ʹ-Hydroxy-3ʹ-methoxyphenyl)-5-hydroxy-3-decanone, [6]-Gingerol, Zingiber officinale - CAS 23513-14-6 - Calbiochem
Empirical Formula (Hill Notation):
C17H26O4
CAS Number:
Molecular Weight:
294.39
MDL number:

Quality Level

assay

≥95% (HPLC)

form

oil

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

pale yellow

solubility

DMSO: 5 mg/mL

shipped in

ambient

storage temp.

−20°C

InChI

1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-17(21-2)16(20)11-13/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3

InChI key

LPRPIMHDDACJHT-UHFFFAOYSA-N

General description

Phytochemical compound isolated from the extract of rhizome of ginger. Along with other related compounds found in ginger extracts inhibits prostaglandin and leukotriene biosynthesis through the suppression of 5-lipoxygenase and prostaglandin synthetase. Also exhibits anti-tumor and apoptosis-inducing effects. Blocks EGF-induced cell transformation by inhibiting the activation of Activator protein-1 (AP-1). Shown to inhibit the EGF-induced, sequence-specific DNA-binding of AP-1. Does not effect EGF-induced phosphorylation of ERK or p38 kinases. Also increases the Ca2+-ATPase activity of the sarcoplasmic reticulum (EC50 = 4 µM).
An antitumor, apoptosis-inducing compound of the ginger family that blocks EGF-induced cell transformation by inhibiting the activation of Activator Protein-1 (AP-1). Also increases the Ca2+-ATPase activity in cardiac sarcoplasmic reticulum (EC50 = 4 µM) and increases Ca2+ uptake.

Packaging

5 mg in Plastic ampoule
Packaged under inert gas

Biochem/physiol Actions

EC50 = 4 µM increasing the Ca2+-ATPase activity in cardiac sarcoplasmic reticulum
Product does not compete with ATP.
Reversible: no
Cell permeable: no
Primary Target
Activator Protein-1 (AP-1)

Warning

Toxicity: Harmful (C)

Reconstitution

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months -20°C.

Other Notes

Bode, A.M., et al. 2001. Cancer Res.61, 850.
Antipenko, A.Y., et al. 1999. J. Pharmacol. Exp. Ther.290, 227.
Park, K.K.,et al. 1998. Cancer Lett.129, 139.
Kobayashi, M., et al. 1987. Biochim. Biophys. Acta903, 96.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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