Deguelin

Base Information

• Chemical Name: Deguelin
• CAS No.: 522-17-8
• Molecular Formula: C₂₃H₂₂O₆
• Molecular Weight: 394.424
• Hs Code.: 29329990
• UNII: K5Z93K66IE
• DSSTox Substance ID: DTXSID10200231
• Nikkaji Number: J6.618D
• Wikipedia: Deguelin
• Wikidata: Q5251862
• NCI Thesaurus Code: C63666
• Pharos Ligand ID: YDML7WX7CDZZ
• Metabolomics Workbench ID: 22665
• ChEMBL ID: CHEMBL393417
• Mol file: 522-17-8.mol

Synonyms:13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one;deguelin

Chemical Property of Deguelin

Chemical Property:

• Vapor Pressure: 1.41E-12mmHg at 25°C
• Melting Point: 85-87 °C(lit.)
• Refractive Index: 1.583
• Boiling Point: 560.127 °C at 760 mmHg
• Flash Point: 244.739 °C
• PSA: 63.22000
• Density: 1.255 g/cm³
• LogP: 4.00790
• Storage Temp.: −20°C
• Solubility.: DMSO: >10 mg/mL
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 394.14163842
• Heavy Atom Count: 29
• Complexity: 674

Purity/Quality:

98%,99%, ^*data from raw suppliers

Deguelin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C=CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC)C
• Isomeric SMILES: CC1(C=CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC)C
• Description: Rotenoids, deriving from the flavonoid family of compounds, act as chemopreventive agents that inhibit NADH:ubiquinone oxidoreductase activity and suppress phorbol ester-induced ornithine decarboxylase (ODC) activity. The rotenoid compound deguelin, originally isolated from the bark of M. sericea (Leguminosae) to be used as an insecticide and fish poison, has chemopreventive and chemosensitizing effects in models of skin, mammary, colon, and lung carcinogenesis. Deguelin inhibits cell growth (IC50 = <10-8 M), blocks PI3K/Akt activation, suppresses COX-2 expression, and induces apoptosis in premalignant and squamous human bronchial epithelial (HBE) cells without affecting normal HBE cells. At 6 mg/kg, deguelin induces Parkinson’s disease-like symptoms in rats after six days of subcutaneous infusion and therefore may also serve as a useful model for Parkinson’s disease research.
• Uses: antineoplastic, antiviral, insecticide, ornithine decarboxylate inhibitor Deguelin exhibits potent apoptotic and antiangiogenic activities in a variety of transformed cells and cancer cells. Deguelin also exhibits potent tumor suppressive effects in xenograft tumor models for many human cancers. (?)-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) cellsan analytical standard in high-performance liquid chromatography (HPLC)

Technology Process of Deguelin

There total 65 articles about Deguelin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

(6aS,12aS,5'S)-5'-phenylsulfinyl-4',5'-dihydrodeguelin (145455-05-6) → (-)-deguelin (522-17-8,54324-46-8,110508-99-1,123000-18-0)

Guidance literature:

In toluene; Heating;

Reference yield: 84.0%

(6aS,12aS,5'S)-5'-(phenylseleno)dihydrodeguelin (70145-45-8) → (-)-deguelin (522-17-8,54324-46-8,110508-99-1,123000-18-0)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; a) 0-5 deg C, 1 h, b) r.t, 18 h;

Reference yield: 82.0%

C23H24O6 → (-)-deguelin (522-17-8,54324-46-8,110508-99-1,123000-18-0)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 6.5h; Inert atmosphere;

DOI:10.1055/s-0037-1611654

upstream raw materials:

(-)-deguelin

(+/-)-trans-deguelin

(6,7-dimethoxy-2H-chromen-4-yl)(4-methoxy-2,2-dimethyl-2H-chromen-6-yl)methanone

3,4-dimethoxyphenol

Downstream raw materials:

cis-deguelin

(1S,2R,7aS,13aS)-1-Chloro-9,10-dimethoxy-3,3-dimethyl-2-phenylsulfanyl-2,3,13,13a-tetrahydro-1H,7aH-pyrano[2,3-c;6,5-f']dichromen-7-one

(+/-)-trans-deguelin

tephrosin

Refernces

• 1、 Xu, Shengtao,Wang, Guangyu,Xu, Feijie,Li, Wenlong,Lin, Aijun,Yao, Hequan,Xu, Jinyi. "Concise Total Synthesis of (±)-Deguelin and (±)-Tephrosin Using a Vinyl Iodide as a Key Building Block". . p. 1055 - 1059. Retrieved 2018/05/07.
• 2、 -. "NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT". Paragraph 0482-0486. . Retrieved 2015/05/26.