D0817

(−)-Deguelin

>98% (HPLC), powder

• Synonym(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
• Empirical Formula (Hill Notation): C₂₃H₂₂O₆
• CAS Number: 522-17-8
• Molecular Weight: 394.42
• MDL number: MFCD01740600
• UNSPSC Code: 12352200
• PubChem Substance ID: 329798641
• NACRES: NA.77

Properties

• assay: >98% (HPLC)
• form: powder
• optical activity: [α]/D -70 to -80°, c = 0.2 in methanol
• color: white to beige
• mp: 85-87 °C (lit.)
• solubility: DMSO: 10 mg/mL, clear
• storage temp.: −20°C
• SMILES string: 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
• InChI key: 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)

Biochem/physiol Actions

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)