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).

• Synonym(e): [6]-Gingerol, Zingiber officinale, 1-(4ʹ-Hydroxy-3ʹ-methoxyphenyl)-5-hydroxy-3-decanone
• Empirische Formel (Hill-System): C₁₇H₂₆O₄
• CAS-Nummer: 23513-14-6
• Molekulargewicht: 294.39
• MDL-Nummer: MFCD00210507
• UNSPSC-Code: 12352200
• NACRES: NA.77

Eigenschaften

• Qualitätsniveau: 100
• Assay: ≥95% (HPLC)
• Form: oil
• Hersteller/Markenname: Calbiochem^®
• Lagerbedingungen: OK to freeze; protect from light
• Farbe: pale yellow
• Löslichkeit: DMSO: 5 mg/mL
• Versandbedingung: ambient
• Lagertemp.: −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
• InChIKey: LPRPIMHDDACJHT-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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. Wirkung

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

Verpackung

Packaged under inert gas

Warnhinweis

Toxicity: Harmful (C)

Rekonstituierung

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

Sonstige Hinweise

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.

Rechtliche Hinweise

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

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315,H319,H335
• P-Sätze: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 10 - Combustible liquids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable