D0817

(−)-Deguelin

>98% (HPLC), powder

• Synonyme(s) : (7aS,13aS)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6′,5′-e]pyran-7(7aH)-one
• Formule empirique (notation de Hill) : C₂₃H₂₂O₆
• CAS Number: 522-17-8
• Poids moléculaire : 394.42
• Numéro MDL: MFCD01740600
• Code UNSPSC : 12352200
• ID de substance PubChem : 329798641
• Nomenclature NACRES : NA.77

Propriétés

• Niveau de qualité: 100
• Essai: >98% (HPLC)
• Forme: powder
• Activité optique: [α]/D -70 to -80°, c = 0.2 in methanol
• Couleur: white to beige
• Pf: 85-87 °C (lit.)
• Solubilité: DMSO: 10 mg/mL, clear
• Température de stockage: −20°C
• Chaîne SMILES: COc1cc2OC[C@H]3Oc4c(ccc5OC(C)(C)C=Cc45)C(=O)[C@H]3c2cc1OC
• InChI: 1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1
• Clé InChI: ORDAZKGHSNRHTD-UXHICEINSA-N

Description

Application

(−)-Deguelin has been used as:

• a nicotinamide adenine dinucleotide hydrogen (NADH) dehydrogenase (Complex I) inhibitor to study its effects on mitochondrial respiratory inhibition in human hepatocarcinoma cells (HepG2) and human renal proximal tubule epithelial cells (RPTECs)
• an antiviral compound to study inhibitory effects on human cytomegalovirus (HCMV)-infected human foreskin fibroblast (HFF) cells
• an analytical standard in high-performance liquid chromatography (HPLC)

Actions biochimiques/physiologiques

Deguelin is a natural rotenoid compound present abundantly in barks, leaves, seeds, and roots of the plants belonging to the Leguminosae family. Deguelin has been studied as a therapeutic agent against the skin, lung cancer, and mammary tumorigenesis.

Inhibitor of activated Akt. Does not affect MAPK, ERK1/2, or JNK. Anticancer, chemoprotective agent.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)