SILYBIN A
silymarin
CAS: 22888-70-6;65666-07-1
Molecular Formula: C25H22O10
SILYBIN A - Names and Identifiers
| Name | silymarin |
| Synonyms | Silybin SILYBIN Silibinin SILYMARIN silymarin SILYBININ SILIBININ SILYBIN A SILYMARIN I SILYBIN (MIX) silymarin group Silybum marianum SILYBIN (A AND B) Silybum Extract 2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-6-(3,5,7-trihydroxy-4-oxobenzopyran-2-yl)benzodioxin (2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one |
| CAS | 22888-70-6 65666-07-1 |
| EINECS | 245-302-5 |
| InChI | InChI=1/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23-,24-,25+/m0/s1 |
SILYBIN A - Physico-chemical Properties
| Molecular Formula | C25H22O10 |
| Molar Mass | 482.44 |
| Density | 1.527±0.06 g/cm3(Predicted) |
| Melting Point | 164-174°C |
| Boling Point | 793.0±60.0 °C(Predicted) |
| Specific Rotation(α) | D20 +11° (c = 0.25 in acetone + alcohol) |
| Flash Point | 274.4°C |
| Water Solubility | 54mg/L(24.99 ºC) |
| Solubility | Easily soluble in acetone, ethyl acetate, methanol, ethanol, slightly soluble in chloroform, almost insoluble in water. |
| Vapor Presure | 1.63E-26mmHg at 25°C |
| Appearance | White-like crystalline powder |
| Color | Pale Yellow |
| Merck | 13,8607 |
| pKa | pKa 6.42±0.04 (Uncertain) |
| Storage Condition | -20°C |
| Stability | Stable. Incompatible with strong oxidizing agents, strong bases. |
| Refractive Index | 1.684 |
| MDL | MFCD03225424 |
| Physical and Chemical Properties |
|
| Use | Has obvious liver protection effect, suitable for acute and chronic hepatitis, early cirrhosis, etc |
| In vitro study | Silibinin is A mixture of two enantiomers of silibinin A and silybinin B in approximately equimolar ratio. Both in vitro and animal studies have shown that silibinin has a hepatoprotective effect (anti-hepatotoxicity) and protects liver cells from toxic damage. In in vitro assays, Silibinin has anticancer effects on human prostate cancer cells, estrogen-dependent and non-dependent human breast cancer cells, human cervical cancer cells, human colon cancer cells, small and non-small human lung cancer cells. |
SILYBIN A - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection S24/25 - Avoid contact with skin and eyes. S22 - Do not breathe dust. S36 - Wear suitable protective clothing. |
| UN IDs | 3172 |
| WGK Germany | 3 |
| RTECS | DJ2981770 |
| HS Code | 29329990 |
| Toxicity | LD50 intravenous in mouse: 1056mg/kg |
SILYBIN A - Reference
| Reference Show more | 1. Xu Jinghan, Xue Yun, Wang Yan, et al. Rapid separation and detection of 7 diastereomers in silymarin by core-shell chromatography-high performance liquid chromatography [J]. Chemistry and Bioengineering, 2017, 06(v.33;No.222):69-74. 2. Wang Li, Yang Shuo, Ma Weiyang, et al. Preparation and Release Mechanism of Silybin Controlled Release Preparation [J]. Chinese Herbal Medicine, 2015(08):1145-1150. 3. Wang Li, Xue Bing, Liu Huashi, et al. Preparation of Silybin meglumine osmotic pump tablets and investigation of its release mechanism [J]. Chinese Journal of Pharmaceutical Industry, 2018. 4. Zhang Huifang, Yang Aachen, Zhang Jiuliang, etc. protective effect of polyphenols from rape bee pollen processing by-products on acute liver injury in mice [J]. Journal of Food Safety and Quality Testing, 2018, v.9(09):59-66. 5. Zhong Jinqiu, Cao Yuzhu, Xu Hongjiang, et al. Study on the effect of diammonium glycyrrhizinate on improving liver injury induced by ConA in mice [J]. Research and Development of Natural Products, 2018, 30(12):60-68. 6. Zheng Chengfeng, Pan Yutian, Yuan Xiaoning, et al. Analysis and Identification of Polyphenolic Compounds in Artichoke by HPLC-UV-MS Method [J]. Journal of Zhangzhou Normal University (Natural Science Edition) 2013(3):81-87. 7. Zhang Lifang, Lin Xia, Feng Xinghai, et al. Optimization of Ultrasonic-assisted Reflux Extraction of Silymarin from Silymarum Seeds with Organic Solvents [J]. Chinese patent medicine, 2019, 41(001):185-188. 8. Qin Shuai, Wu Lili, Qin Lingling, Zhang Chengfei, Wu Youyou, Sun Boju, Liu Tonghua. Effect and mechanism of silybin on insulin resistance in C2C12 cells [J]. World Science and Technology-Modernization of Traditional Chinese Medicine, 2020,22(10):3450-3455. 9. Jie Chen, Dong-Li Li, Ling-Na Xie, Yu-ran Ma, Pan-Pan Wu, Chen Li, Wen-Feng Liu, Kun Zhang, Ren-Ping Zhou, Xue-Tao Xu, Xi Zheng, Xia Liu, synergistic anti-inflammatory effects of silibinin and thymol combination on LPS-induced RAW264.7 cells by inhibition 10. Li, Fang, et al. "Lactobacillus fermentum HFY06 reduced CCl 4-induced hepatic damage in Kunming mice." RSC Advances 10.1 (2020): 1-9.https:// doi.org/10.1039/C9RA08789C 11. [IF = 4.5] Wang Min et al. "Silibinin Prevents Autophagic Cell Death upon Oxidative Stress in Cortical Neurons and Cerebral Ischemia-Reperfusion Injury." Mol Neurobiol 2016 Mar;53(2):932-943 12. [IF = 2.977] Yan-Jiao Li et al. "Silibinin exerts antidepressant effects by improving neurogenesis through BDNF/TrkB pathway." Behav Brain Res. 2018 Aug;348:184 13. [IF = 1.908] Yan Chen et al. "Characterization of glutathione conjugates derived from reactive metabolites of seven silymarin isomers." Xenobiotica. 2019;49(11):1269-1278 14. [IF = 11.878] Li Xinming et al. "A fast and specific fluorescent probe for thioredoxin reductase that works via disulphide bond cleavage." Nat Commun. 2019 Jun;10(1):1-12 15. [IF = 4.268] Jie Chen et al. "Synergistic anti-inflammatory effects of silibinin and thymol combination on LPS-induced RAW264.7 cells by inhibition of NF-κB and MAPK activation." Phytomedicine. 2020 Nov;78:153309 16. [IF = 3] Qu Lala et al. "Phenotypic assessment and screening of ETA/ETB receptors with label-free dynamic mass redistribution say." N-S Arch Pharmacol. 2020 Jun;393(6):937-950 17. [IF = 3.246] Xu Renjie et al. "Fabrication of Stable Apigenin Nanosuspension with PEG 400 as Antisolvent for Enhancing the Solubility and Bioavailability." Aaps Pharmscitech. 2022 Jan;23(1):1-11 |
SILYBIN A - Nature
Open Data Verified Data
white crystalline powder. Odorless, slightly bitter, hygroscopic. Insoluble in water and chloroform, soluble in alkaline aqueous solution, slightly soluble in methanol and ethanol, soluble in acetone and ethyl acetate and other organic solvents. Melting point 167 ° C, heated to about 180 ° C decomposition. Specific optical rotation of 11 (acetone)
Last Update：2024-01-02 23:10:35
SILYBIN A - Preparation Method
Open Data Verified Data
general silymarin seeds as raw material extraction. Take 5kg silymarin seed crushing, with petroleum ether (30~60 ℃) defatted for 24h, defatted powder volatilized to petroleum ether after 60 mesh sieve, then with acetone reflux extraction for 32H, concentrate the Acetone Extract to a certain volume
After upper silica gel column, with chloroform: ethanol (95:5) elution, and identified by thin layer chromatography collected components, the same spots combined, reduced pressure concentration to dry, the main spots can be obtained light yellow crystals, with a small amount of methanol wash 2 times, after drying to obtain silymarin crude crystal 22.5g, the yield is 0. 45%. The crude crystals were soaked with a small amount of acetone, stirred and allowed to stand for 2 days, and the acetone solution was filtered to obtain a white powder, which was dried. A sample of the dried white powder was taken. 200ml of distilled water was added to 5G, the pH value was adjusted to 9 to 10 with 1 mol/L NaOH solution, and the whole was dissolved by slight heating. Then, 500ml of chloroform was added, and the chloroform layer was separated by shaking. The chloroform layer solution was concentrated to dryness under reduced pressure to give a white powder. Dissolve the white powder with acetone, filter, concentrate the acetone to a certain volume, add petroleum ether (60~90 ℃) to slightly turbid, and place overnight to obtain crystallization. According to this step, the product was crystallized twice with acetone petroleum ether and dried in a vacuum drying oven to obtain pure silymarin.
Last Update：2022-01-01 11:15:06
SILYBIN A - Use
Open Data Verified Data
This product is mainly used for the treatment of acute and chronic hepatitis, fatty liver, liver cirrhosis, liver damage caused by alcohol, metabolic toxic liver damage, gallstones and spleen disease.
Last Update：2022-01-01 11:15:07
SILYBIN A - Reference Information
| plant source: | milk thistle |
| Silybum marianum extract | Silybin is a flavonoid lignan compound isolated from the seeds of the Compositae plant Purple Silybum marianum. The main active ingredients are Silybin, isosybinin, Silybum marianum and Silyphine, which can prevent damage to the liver caused by chemical toxins, food toxins and drugs, and promote the regeneration and repair of liver cells, it is called "natural hepatoprotective medicine". White crystalline powder at room temperature, odorless, slightly bitter taste, hygroscopic, soluble in acetone, ethyl acetate, methanol, ethanol, slightly soluble in chloroform, almost insoluble in water. Silibinin is also known as heparin, milk thistle, milk thistle, milk thistle total flavonoids, silimaling, yiganling, silymarin, ligalon, as early as 2000 years ago, the ancient Chinese used milk thistle to treat liver and gallbladder diseases, clinical shows that it has obvious protection and stability of liver cell membrane; it has different degrees of protective and therapeutic effects on various types of liver injury caused by liver poisons such as carbon tetrachloride, thioacetamide, muscarinic, phalloidin, and has a certain preventive effect on the increase of alanine aminotransferase caused by carbon tetrachloride. It is suitable for the treatment of chronic persistent hepatitis, chronic active hepatitis, initial cirrhosis, liver poisoning and other diseases. In addition, this product also has strong antioxidant properties, can remove free radicals in the human body, delay aging, and has been widely used in medicine, health products, food and cosmetics and other fields. |
| biological activity | Silibinin (Silybin, Silibinin A, Silymarin I) is the main active ingredient of Silymarin. |
| use | has obvious liver protection effect and is suitable for acute and chronic hepatitis, early liver cirrhosis, etc. silibinin is a mixture of two enantiomers of AB with an approximate equimolar ratio. |
Last Update：2024-04-09 21:54:55
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