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Sigma-Aldrich

[6]-Gingerol, Zingiber officinale

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).

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Synonym(s):
[6]-Gingerol, Zingiber officinale, 1-(4ʹ-Hydroxy-3ʹ-methoxyphenyl)-5-hydroxy-3-decanone
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

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This Item
G104650866PHL89201
[6]-Gingerol ≥98% (HPLC)

Sigma-Aldrich

G1046

[6]-Gingerol

[6]-Gingerol analytical standard

Supelco

50866

[6]-Gingerol

6-Gingerol phyproof® Reference Substance

PHL89201

6-Gingerol

form

oil

form

-

form

-

form

-

manufacturer/tradename

Calbiochem®

manufacturer/tradename

-

manufacturer/tradename

-

manufacturer/tradename

PhytoLab

storage condition

OK to freeze, protect from light

storage condition

protect from light, under inert gas

storage condition

-

storage condition

-

color

pale yellow

color

-

color

-

color

-

solubility

DMSO: 5 mg/mL

solubility

methanol: 1 mg/mL, clear, colorless

solubility

-

solubility

-

General description

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.
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).

Biochem/physiol Actions

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

Packaging

Packaged under inert gas

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


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