Cinchonine
Cinchonine
CAS: 118-10-5
Molecular Formula: C19H22N2O
Cinchonine - Names and Identifiers
| Name | Cinchonine |
| Synonyms | CINCHONINE Cinchonine D-CINCHONINE (+)-cinconine cinchonan-9-ol (+)-CINCHONINE (9s)-cinchonan-9-o (8r,9s)-cinchonine (9R)-cinchonan-9-ol (9S)-Cinchonan-9-ol (9S)-cinchonan-9-ol CINCHONAN-9-OL,(9S)- (8alpha,9S)-cinchonan-9-ol (3alpha,9S)-cinchonan-9-ol (3alpha,9R)-cinchonan-9-ol (9S)-9-hydroxycinchonan-1-ium (4beta,9S)-cinchonan-1-ium-9-ol alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol |
| CAS | 118-10-5 |
| EINECS | 204-234-6 |
| InChI | InChI=1/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/p+1/t13-,14-,18+,19-/m0/s1 |
| InChIKey | KMPWYEUPVWOPIM-QHQSXHFQSA-N |
Cinchonine - Physico-chemical Properties
| Molecular Formula | C19H22N2O |
| Molar Mass | 294.39 |
| Density | 1.0863 (rough estimate) |
| Melting Point | 260-263°C |
| Boling Point | 436.16°C (rough estimate) |
| Specific Rotation(α) | 224 º (c=0.5, alcohol) |
| Flash Point | 234.723°C |
| Water Solubility | Insoluble |
| Solubility | Insoluble in water |
| Vapor Presure | 0Pa at 25℃ |
| Appearance | Bright light brown crystal |
| Color | White to light beige |
| Merck | 14,2287 |
| BRN | 89689 |
| pKa | 5.85, 9.92(at 25℃) |
| PH | 9.0 (0.25g/l, H2O, 20℃)(as aqueous solution) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Stability | Stable, but may be light sensitive. Incompatible with strong oxidizing agents. |
| Sensitive | Light Sensitive |
| Refractive Index | 223 ° (C=0.5, EtOH) |
| MDL | MFCD00064372 |
Cinchonine - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R20/22 - Harmful by inhalation and if swallowed. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | 1544 |
| WGK Germany | 3 |
| RTECS | GD3500000 |
| FLUKA BRAND F CODES | 8-34 |
| HS Code | 29339900 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 i.p. in rats: 152 mg/kg (Johnson, Poe) |
Cinchonine - Reference Information
| LogP | 2.82 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Application | Cinchonine,(1S)-quinolin-4-yl (5-vinylquinin-2-yl) methanol, is a quinoline-type alkaloid, a kind of cinchona alkaloid, also known as cinchona, weak cinchona, is a stereoisomer of cinchona. Cinkonin is an alkaloid with more content except quinine in cinchona bark. Cinkonin is an essential analytical reagent for the determination of tungsten ore by gravimetric analysis. Cinkonin and its derivatives are widely used in the preparation, separation and analysis of chiral drugs and chiral intermediates. |
| anti-tumor application | the effect of cinkoning on tumor cell growth, and then it is determined that cinkoning can promote tumor cell apoptosis. the above experimental results show that cinkoning can inhibit tumor cell growth, promote early tumor apoptosis, enhance the expression of promoting cell apoptosis factors, and inhibit the expression of inhibiting apoptosis factors. Cinkonin is expected to be used in anti-tumor applications in the future. |
| preparation method | (1) preparation of raw material a: mixing cinchona bark (30-60 mesh powder) and toluene equivalent to 6 times the volume of cinchona bark, heating and refluxing at 80-90 ℃ for 4 times and then concentrating, and the total alkaloid extract obtained is dissolved in dilute sulfuric acid solution with a concentration of 10% by mass, the pH value of the solution is between 3 and 4, the filtrate is heated to 60~70 ℃ after filtration, sodium hydroxide with a concentration of 10% mass percentage is added under stirring to adjust the pH value of the solution to 6.5~7.0, and quinine sulfate is precipitated after standing for cooling, and quinine sulfate solid is filtered out. Then add sodium hydroxide solution with a concentration of 20% mass percentage to the filtrate to adjust the pH value of the solution to 10, place it, precipitate the total solids of the remaining cinchona alkaloids, filter out the solids, and then dry at 60~70 ℃ under normal pressure to obtain raw material A. (2) weigh 3.5g of raw material Ainto a 100mL round bottom flask, add 60mL of ethyl acetate, stir for 30min at room temperature, let stand for 6h, and filter to obtain filtrate B and insoluble substance c. Concentrate the filtrate B to one-tenth of the original volume and place it at room temperature until the crystallization is complete. After filtering out the crystallization, it is dissolved in ethanol solution with a volume fraction of 95%. 0.15 grams of activated carbon is decolorized and recrystallized to obtain 1.2 grams of white solid. The yield is 34%. It is white amorphous or crystalline powder, dissolved in ethanol, easily soluble in chloroform, and slightly soluble in ether, the specific rotation is 255 °(0.5mol/L ethanol solution), the melting point is 172-174 ℃, and the content determined by perchloric acid titration is 99.6%; the white solid sample is identified by thin layer chromatography The results are consistent with the standard, and the melting point of the sample is determined after mixing with the standard, which confirms that the white solid is quinidine. dissolve insoluble substance c with 95% volume fraction of ethanol, add 0.15g of activated carbon, keep 75 ℃ stirring for decolorization for 25 minutes, filter to remove activated carbon, and obtain 0.72g of white crystalline powder with 21% yield. The appearance of this product is white powder, dissolved in ethanol and chloroform, and slightly soluble in ether. The specific rotation is +225 (0.5mol/L ethanol solution), the melting point is 258-260 ℃, and the content is 98.5% by perchloric acid titration. The sample was identified by thin layer chromatography with the same results as the standard, the sample mixed with the standard after the determination of melting point does not change, the identification of the white powder for cinchonine. |
| Cinchona alkaloid | Cinchona is a quinoline-type alkaloid, a kind of Cinchona alkaloid, also known as Cinchona, weak Cinchona is the stereoisomer of Cinchona. Molecular formula C19H22N2O. Molecular weight 294.40. White needle-like or prismatic crystals obtained from ether. Melting point 58~60 ℃,[α]D15 48 (ethanol, C = 1). Sublimation begins at 220 ℃. Soluble in alcohol, ether, acetone, benzene and chloroform, almost insoluble in cold water. The color becomes darker under light, and its aqueous solution is mostly or almost completely converted into occinotoxin by phosphoric acid and organic acid (especially acetic acid) at 98~100 ℃, while no or only a small amount of this conversion occurs in hydrochloric acid. In hydrochloric acid or acetic acid, palladium-catalyzed hydrogenation obtains dihydrocinchonine, and in acetic acid, platinum-catalyzed hydrogenation at 50°C to obtain hexahydrocinchonine. This product naturally exists in the Rubiaceae cinchona plants. In 1820, French chemists Pierre Peltier (PierrePelletier) and Joseph Caventu (JosephCaventou) first separated from cinchona bark. Two active organisms (alkaloids), the active ingredients quinine and golden chicken ning (cinchonine), can treat various malaria clinically. It can also be used as bismuth and tungsten reagents. It can be obtained by reacting octanine ketone with ethanol and sodium, or reducing it with iron in acetic acid. |
| Use | Cinconine is a stereoisomerism of Cinconidine. Antimalarial drugs. |
| Production method | 1. Plant sources include the bark of red cinchona tree and cinchona bark of Rubiaceae. It can also be biosynthesized and can be made into hydrochloride and tartrate. It has anti-plasmodium and antipyretic effects. 2. Alkaloids can be obtained from the bark of cinchona after extraction. The crude product is dissolved in nitric acid and then precipitated with ammonia water. The white precipitate obtained is cinkonin. |
Last Update：2024-04-09 20:52:54
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