Tangeretin, froM Citrus nobilis Lour.
5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4-benzopyrone
CAS: 481-53-8
Molecular Formula: C20H20O7
Tangeretin, froM Citrus nobilis Lour. - Names and Identifiers
| Name | 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4-benzopyrone |
| Synonyms | NSC 53909 Tangeretin NSC 618905 TANGERITIN TANGERETIN Tangeretin 481-53-8 Tangeretin, froM Citrus nobilis Lour. 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4-benzopyrone 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 4H-1-Benzopyran-4-one, 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)- |
| CAS | 481-53-8 |
| EINECS | 207-570-1 |
| InChI | InChI=1/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3 |
Tangeretin, froM Citrus nobilis Lour. - Physico-chemical Properties
| Molecular Formula | C20H20O7 |
| Molar Mass | 372.37 |
| Density | 1.244±0.06 g/cm3(Predicted) |
| Melting Point | 153.0 to 157.0 °C |
| Boling Point | 565.3±50.0 °C(Predicted) |
| Flash Point | 248.4°C |
| Solubility | Soluble in methanol, DMSO and other solvents. |
| Vapor Presure | 8.41E-13mmHg at 25°C |
| Appearance | Yellow crystal |
| BRN | 351695 |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.565 |
| MDL | MFCD00017438 |
| Physical and Chemical Properties | Soluble in methanol, DMSO and other solvents. Citrus nobilis Peel from Rutaceae |
Tangeretin, froM Citrus nobilis Lour. - Risk and Safety
| Risk Codes | R25 - Toxic if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 2811 |
| WGK Germany | 3 |
| RTECS | DJ3102725 |
| HS Code | 29329990 |
Tangeretin, froM Citrus nobilis Lour. - Reference Information
| Overview | Tangeretin is one of the effective components of orange peel, which has been proved to belong to phenolic compounds, properties are colorless crystals or crystalline powder, odor aromatic, melting point 50 ℃ ~ 51 ℃, boiling point 232 ℃, volatile, difficult to dissolve in water, soluble in ethanol, ether and other organic solvents, it has a good effect on the treatment of animal acariasis. Compared with organic phosphorus, organic nitrogen and organic chlorine, it has the advantages of small toxic and side effects, low residue and no environmental pollution. For clinical treatment, there are disadvantages such as high cost, not easy to make easy to use the preparation and so on. Hesperidin is widely used in organic chemistry and life science. As the content of hesperidin in plants is low, and the price is expensive, so the study of hesperidin in our country is lagging behind. China is rich in citrus resources, and the extraction and application of hesperidin have broad prospects. figure: Orange Peel |
| Source | hesperidin and naringin, hesperidin, nobiletin and other flavonoids coexist in Rutaceae or Euphorbiaceae plants. |
| extraction | hesperidin is mainly extracted from plants of Rutaceae or Euphorbiaceae, and the extraction methods include recrystallization, column chromatography, high-speed countercurrent chromatography and supercritical carbon dioxide extraction. recrystallization method: Danxi orange is a famous citrus variety in the United States. The study found that the cold pressed orange oil made from Danxi Orange was centrifuged and frozen for a long time to form a yellow precipitate, and further removed limonene and recrystallized to obtain white crystalline hesperidin. As a by-product, the coproduction of hesperidin with cold-pressed orange oil can greatly reduce its production cost. column chromatography: column chromatography is a method of extracting hesperidin from sweet orange, fructus aurantii, Danxi orange and Croton pubescens by mixed organic solvent gradient elution. High-Speed Countercurrent Chromatography: High-Speed Countercurrent Chromatography, (HSCCC) is a liquid-liquid partition chromatography technique. Compared with other chromatographic separation methods, HSCCC does not use any solid carrier or support as a stationary phase, and the sample only realizes efficient separation and pure product preparation in a short time by the difference of distribution between immiscible two-phase solvents, in recent years, it has been paid attention to and applied in the field of extraction of natural products. supercritical carbon dioxide extraction method: supercritical carbon dioxide has a special effect on the dissolution of some natural products. The principle of supercritical carbon dioxide extraction technology is to use the relationship between the solubility of supercritical carbon dioxide and its density, that is, the extraction is carried out by using the influence of pressure and temperature on the solubility of supercritical carbon dioxide. In the supercritical state, the supercritical carbon dioxide is contacted with the substance to be separated, so that it selectively extracts the components of different polarity, boiling point and molecular weight in sequence, and then uses reduced pressure, the supercritical fluid is changed into ordinary gas by heating, and the extracted substance is completely or basically precipitated, so as to achieve the purpose of separation and purification. |
| Application | Medicine: hesperidin has a good inhibitory effect on liver cancer cell line SMMC -7721, hesperidin can effectively inhibit the growth of leukemia cancer cells by HL-60, and has no obvious toxic and side effects on normal immune cells. In addition, hesperidin can be used in the treatment of oral cancer and in the treatment of breast cancer. Zoology: Tangerine can treat animal acariasis, and the toxic side effect is small, the residue is low, has the advantages of Chinese herbal medicine preparation. |
| references | [1] Yu Hongwei, Han Weirong, Peng on Tuesday, etc. Research progress on extraction and application of hesperidin [J]. Jiangsu Agricultural Sciences, 2012, 40(3):249-252. [2] Xu Lanying, Zhao Hui, Zhang Ting, etc. Extraction, isolation and modification of hesperidin and its inhibitory effect on human hepatic stellate cell LX-2 [J]. Food Science, 2015, 36(23):43-46. [3] Li Jinyan. Effects of hesperidin on proliferation and apoptosis of human glioblastoma cells [J]. Gerontology of China, 2017, 37(12). |
| Chemical properties | soluble in methanol, DMSO and other solvents. |
| Use | hesperidin is a flavonoid found in the peel of citrus fruits and has natural antifungal properties. Hesperidin has been shown to inhibit intercellular communication induced by anti-tumor promoters and cell proliferation of some cancer cell lines A flavonoid found in the peel of citrus fruits, inhibition of anti-tumor promoter-induced intercellular communication and inhibition of cell proliferation in several cancer cell lines has been demonstrated. |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
Last Update：2024-04-09 21:54:55
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