Skip to Content
MilliporeSigma
All Photos(1)

Documents

345868

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).

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C17H26O4
CAS Number:
Molecular Weight:
294.39
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

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

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service