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).

• Sinónimos: [6]-Gingerol, Zingiber officinale, 1-(4ʹ-Hydroxy-3ʹ-methoxyphenyl)-5-hydroxy-3-decanone
• Fórmula empírica (notación de Hill): C₁₇H₂₆O₄
• Número de CAS: 23513-14-6
• Peso molecular: 294.39
• Número MDL: MFCD00210507
• Código UNSPSC: 12352200
• NACRES: NA.77

Propiedades

• Nivel de calidad: 100
• descripción: RTECS - HE0757000
• Ensayo: ≥95% (HPLC)
• Formulario: oil
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; protect from light
• color: pale yellow
• solubilidad: DMSO: 5 mg/mL
• Condiciones de envío: ambient
• temp. de almacenamiento: −20°C
• cadena SMILES: 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
• Clave InChI: LPRPIMHDDACJHT-UHFFFAOYSA-N

Descripción

Descripción general

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).

Acciones bioquímicas o fisiológicas

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

Envase

Packaged under inert gas

Advertencia

Toxicity: Harmful (C)

Reconstitución

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

Otras notas

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.

Información legal

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

Información de seguridad

• Pictogramas: GHS07
• Palabra de señalización: Warning
• Frases de peligro: H315,H319,H335
• Consejos de prudencia: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Clasificaciones de peligro: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Órganos de actuación: Respiratory system
• Código de clase de almacenamiento: 10 - Combustible liquids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable