345868

[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).

• Synonyma: [6]-Gingerol, Zingiber officinale, 1-(4ʹ-Hydroxy-3ʹ-methoxyphenyl)-5-hydroxy-3-decanone
• Empirický vzorec (Hillův zápis): C₁₇H₂₆O₄
• Číslo CAS: 23513-14-6
• Molekulová hmotnost: 294.39
• MDL number: MFCD00210507
• UNSPSC Code: 12352200
• NACRES: NA.77

Vlastnosti

• Quality Level: 100
• description: RTECS - HE0757000
• 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
• SMILES string: O(C)c1c(cc(cc1)CCC(=O)CC(O)CCCCC)O
• 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

Popis

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

Bezpečnostní informace

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• 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