4'-Demethylepipodophyllotoxin CAS 6559-91-7
4'-Demethylepipodophyllotoxin Basic information
| Product Name: | 4'-Demethylepipodophyllotoxin |
| Synonyms: | (5R)-5,8,8aβ,9-Tetrahydro-9α-hydroxy-5β-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aαH)-one;(5R)-5β-(3,5-Dimethoxy-4-hydroxyphenyl)-7α-(hydroxymethyl)-8α-hydroxy-5,6,7,8-tetrahydronaphtho[2,3-d]-1,3-dioxole-6β-carboxylic acid 6,7-lactone;(5R)-5β-(3,5-Dimethoxy-4-hydroxyphenyl)-9α-hydroxy-5,5aα,6,8,8aβ,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6-one;(5R,5aα,8aβ)-5,8,8a,9-Tetrahydro-5β-(4-hydroxy-3,5-dimethoxyphenyl)-9α-hydroxyfuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;4-Domethylpodophyllotoxin, 4'-demethyl-epi-Podophyllotoxin;4'-O-deMethylepipodophyllotoxin;4-DeMethyl Epipodophyllotoxin(DMEP);Demethylpodophyllotoxin, 4'- |
| CAS: | 6559-91-7 |
| MF: | C21H20O8 |
| MW: | 400.38 |
| EINECS: | 613-823-0 |
| Product Categories: | chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Miscellaneous Natural Products;Plant Oils, Toxins, Phenolic Acids & Derivatives;SiChem |
| Mol File: | 6559-91-7.mol |
4'-Demethylepipodophyllotoxin Chemical Properties
| Melting point | 246-248°C |
| Boiling point | 626.5±55.0 °C(Predicted) |
| density | 1.446±0.06 g/cm3(Predicted) |
| storage temp. | Inert atmosphere,Store in freezer, under -20°C |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| form | Solid |
| pka | 9.94±0.40(Predicted) |
| color | White to Off-White |
| Major Application | pharmaceutical |
| InChIKey | YVCVYCSAAZQOJI-JHQYFNNDSA-N |
| SMILES | O1C2=CC3=C(C=C2OC1)[C@@H](C1=CC(OC)=C(O)C(OC)=C1)[C@@]1([H])C(=O)OC[C@]1([H])[C@@H]3O |
Safety Information
| WGK Germany | WGK 3 |
| HS Code | 29349990 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Carc. 1A Repr. 1A |
| Chemical Properties | Off-White Solid |
| Uses | A potent inhibitor of microtubule assembly. |
| Definition | ChEBI: An organic heterotetracyclic compound that is the 9- epimer of 4'-demethylpodophyllotoxin. |
| Synthesis | 518-28-5 6559-91-7 (5R,5aR,8aR,9R)-9-Hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one (onychocercazylidene, 2.1 g, 5.0 mmol) was used as a raw material and dissolved in anhydrous dichloromethane. Sodium iodide (2.3 g, 15.0 mmol) was added to this solution and stirred for 5 min. The reaction mixture was cooled to 0°C (ice-water bath) and methanesulfonic acid (1.48 mL, 15.0 mmol) was added slowly dropwise, after which stirring was continued and gradually brought to room temperature. The reaction was continued at room temperature for 5 hours, during which time nitrogen was introduced to remove the HI gas generated from the reaction. After completion of the reaction, the solvent was removed by concentration under reduced pressure. The crude product was dissolved in a solvent mixture of acetone-water (25 mL-25 mL), barium carbonate (2.0 g, 10.0 mmol) was added, and the reaction was carried out at 40 °C for 30 min. The reaction solution was diluted with dichloromethane (100 mL), poured into 500 mL of 10% aqueous sodium thiosulfate solution and extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (eluent: chloroform:methanol=92:8) to afford the target product (5R,5aR,8aR,9S)-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxolan-6(8H)-one ( VII, 1.8g, 90% yield), as white solid. |
| in vivo | 4'-Demethylepipodophyllotoxin (1 μg/mL, 200 μL, topical application, 24 weeks) reduces the tumor incidence, tumor volume, and the conversion efficiency of papillomas to squamous cell carcinomas in DMBA/TPA-induced mouse skin carcinogenesis model[1]. |
| References | [1] Synthetic Communications, 2012, vol. 42, # 18, p. 2780 - 2789 [2] Patent: CN104098594, 2016, B. Location in patent: Paragraph 0040-0041 [3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 3, p. 901 - 906 [4] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4851 - 4856 [5] Journal of Medicinal Chemistry, 1998, vol. 41, # 23, p. 4475 - 4485 |
4'-Demethylepipodophyllotoxin Preparation Products And Raw materials
| Raw materials | Podophyllotoxin-->Sodium iodide-->Acetone-->Methanesulfonic acid-->Water-->Barium carbonate-->Dichloromethane |
