3α,16α-Eburnamonine
(-)-Eburnamonine
CAS: 4880-88-0
Molecular Formula: C19H22N2O
3α,16α-Eburnamonine - Names and Identifiers
| Name | (-)-Eburnamonine |
| Synonyms | VINCAMONE vinburnine (-)-EBURNAMONINE (-)-eburnamonina (-)-Eburnamonine EBURNAMONINE, (-)- 3α,16α-Eburnamonine EBURNAMONINE, (-)-(RG) 14,15-dihydroeburnamenin-14-one (3alpha,16alpha)-eburnamenin-14(15H)-one (16alpha)-14,15-dihydroeburnamenin-4-ium-14-one (3alpha,16alpha)-14,15-dihydroeburnamenin-14-one (3alpha,16alpha)-14,15-dihydroeburnamenin-4-ium-14-one |
| CAS | 4880-88-0 |
| EINECS | 225-490-5 |
| InChI | InChI=1/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/p+1/t18-,19+/m1/s1 |
3α,16α-Eburnamonine - Physico-chemical Properties
| Molecular Formula | C19H22N2O |
| Molar Mass | 294.39 |
| Density | 1.34 |
| Melting Point | 174-177°C(lit.) |
| Boling Point | 436.16°C (rough estimate) |
| Specific Rotation(α) | D25 -102° (chloroform) (Clauder); D -100° (c = 0.783 in chloroform) (Cartier) |
| Flash Point | 221°C |
| Solubility | Chloroform (Slightly), Methanol (Slightly, Heated) |
| Vapor Presure | 5.25E-08mmHg at 25°C |
| Appearance | White or light yellow crystalline powder |
| Color | White |
| Merck | 13,3520 |
| pKa | 8.13±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.5600 (estimate) |
| MDL | MFCD00064309 |
3α,16α-Eburnamonine - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 2 |
| RTECS | YY8575570 |
| FLUKA BRAND F CODES | 8-10 |
3α,16α-Eburnamonine - Reference Information
| overview | Changchun Bunin is also called ivory ketonin, which is white or light yellow crystalline powder at room temperature. As a cerebral vasodilator, vinblastine has more obvious vasodilator than vinblastine, and can promote oxygen consumption and brain utilization of glucose. As clinically used to treat ischemic stroke and other diseases caused by cerebrovascular diseases, it has great significance in clinical application. |
| basic information | Chinese name: (-)-ivory (hongdamu) keoning foreign name: Eburnamonine CAS number: 4880-88-0 EINECS number: 225-490-5 molecular formula: C19H22N2O molecular weight: 294.39100 appearance and properties: white powder Chinese alias: Changchun Bunin density: 1.34g/cm3 melting point: 174-177 c (lit.) boiling point: 441.9 c at 760 mmHg flash point: 221 c picture: molecular structure formula |
| application | vinblastine is used as a cerebral vasodilator, which has a more obvious vasodilating effect than vinblastine, and can promote oxygen consumption and brain glucose Utilization. As clinically used to treat ischemic stroke and other diseases caused by cerebrovascular diseases, it has great significance in clinical application. At the same time, this product is also the most deeply and widely studied compound in this family of alkaloids. |
| Synthesis method | At present, the synthesis method of Changchun Bunin is mainly divided into two methods: semi-synthesis and total synthesis. The semi-synthesis of Changchun Bunin is mainly synthesized by using the teponin extracted from horse bell fruit as the starting material, and the total chemical synthesis method is through the reduction of intermediates. The total chemical synthesis method is more suitable for industrialization. The total chemical synthesis method is as follows:(±)-15a-ethyl -2,3,6,11,15,15a-hexahydro -1H, 5H-indolo [2,3-a] pyran [3,2-i] quinazine -14,14-(13H)-dicarboxylic acid diethyl ester is the intermediate structure in the chemical synthesis process of Changchun Bunin, after manual resolution, reduction is carried out to obtain optically active ()-15a-ethyl-2, 3,6,11,15, 15a-hexahydro-1 H, 5H-indolo [2,3-a] pyran [3,2-i] quinazine -14,14-(13H)-dicarboxylic acid diethyl ester (compound I), the effective structure (compound II) of Changchun Bunin product was obtained by subsequent Pd-C reaction Figure: Synthetic route |
| references | [1] yang Qing, Liu jiuzhi, Zhou hong. investigation of influencing factors of palladium-carbon catalytic hydrogenation reduction of Changchun Bunin synthesis intermediates [J]. Guangdong chemical industry, 2014, 41(6):61-62. [2]http://baike.baidu.com/link?url=CzlkRtodVzIznL0E--3I1EEFzWgA0Y_SIdBny2QrkmYsFYxPoKJF5Ja7Qv_MJME1ToQ72euEK-rRjkE1xUZZih_A5rUwvHVX0EYd2uLCemHoaX8wnsUsVKRqo94Zhw9q |
| biological activity | Vincamone is a metabolite of Catharanthus roseus alkaloids and vincamine, and is a vasodilator. |
Last Update：2024-04-09 21:11:58
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