Silybin

Base Information

• Chemical Name: Silybin
• CAS No.: 65666-07-1
• Molecular Formula: C25H22O10
• Molecular Weight: 482.4362
• Hs Code.: 3003909090
• European Community (EC) Number: 613-830-9,678-483-8,806-403-5
• Nikkaji Number: J2.972.067C
• NCI Thesaurus Code: C26671
• ChEMBL ID: CHEMBL9509
• Mol file: 65666-07-1.mol

Synonyms:2,3 Dehydrosilybin;2,3-dehydrosilybin;Alepa forte;Alepa-forte;Ardeyhepan;Cefasilymarin;durasilymarin;Hepa loges;Hepa Merz Sil;hepa-loges;Hepa-Merz Sil;HepaBesch;Hepar Pasc;Hepar-Pasc;Heparsyx;Heplant;Lagosa;legalon forte;silibin;silibinin;Silibinin A;Silibinin B;silybin;silybin A;silybin B;silybinin

Chemical Property of Silybin

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 1.63E-26mmHg at 25°C
• Melting Point: 158 °C
• Refractive Index: 1.684
• Boiling Point: 793 °C at 760 mmHg
• Flash Point: 274.4 °C
• PSA: 155.14000
• Density: 1.527 g/cm³
• LogP: 2.36270
• Storage Temp.: −20°C
• Solubility.: Acetone (Slightly), DMSO (Slightly), Methanol (Very Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 482.12129689
• Heavy Atom Count: 35
• Complexity: 750

Purity/Quality:

98% ^*data from raw suppliers

Silymarin(>80%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
• Isomeric SMILES: COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
• Recent ClinicalTrials: Effect of Silymarin in Metastatic Colorectal Cancer Patients
• Recent EU Clinical Trials: Phase II Clinical Trial to evaluate the efficacy of silibinin supplementation in the prevention of the progression of the respiratory failure in patients with onco-hematological diseases and infection by COVID-19 positive.
• Description: Silymarin is a kind of flavonoid complex consisting of silybin, silydianin, and silychrisin, derived from the milk thistle plant. It is a kind of potent antioxidant, anti-cancer agent as well as liver protecting agent. It has a lot of pharmaceutical functions. For example: (1) Promotes healthy liver function and general health; (2) Strengthen the normal cellular defense system to protect the liver tissue; (3) Help to eliminate the toxin accumulating in the liver; (4) Increase the survival rate of patients of cirrhosis; (5) Protect our body against industrial poisons; (6) Antidote against the death cap mushroom. Silymarin exerts its pharmaceutical effects through various mechanism including scavenging free radicals, increasing glutathione (has detoxifying effect) level in the liver, increasing the levels of antioxidant enzymes such as superoxide dismutase, stimulating liver protein synthesis and inhibiting the synthesis of leukotrienes.
• Physical properties: Silymarin is obtained from silybum marianum (milk thistle), an edible plant that has been used medicinally for centuries as a herbal medicine for the treatment of liver related disorders. The plant is native to the Mediterranean andis widely found in Europe and North America. It also grows in India, China, South America and Australia. This herb is approved for sale in Canada in different products and gains an annual business of 180 million in Germany. Silymarin is a polyphenolic flavonoid, extracted using 95% ethanol, from the seeds of the milk thistle. The plant consists of approximately 70-80% of silymarin flavonolignans and approximately 20-30% undefined fraction. The most prevalent component is Silybin (50-60% of Silymarin). It consists of seven flavonoglignans (silibinin, isosilibinin, silychristin, isosilychristin and silydianin) and a flavonoid (taxifolin).
• Uses: In the United States, milk thistle is most commonly used to treat viral infections and cirrhosis of the liver. Milk thistle (Silybum marianum) was used in classical Greece to treat liver and gallbladder diseases and to protect the liver against toxins. It recently has been investigated for use as a cytoprotectant, an anticarcinogen, and a supportive treatment for liver damage from Amanita phalloides poisoning. Its active ingredient is silymarin, found primarily in the seeds. Silymarin undergoes enterohepatic recirculation, which results in higher concentrations in liver cells than in serum.It is made up of components called flavonolignans, the most common being silybin. Silymarin a flavonolignan complex extracted from milk thistle, has been shown to provide cytoprotective, antioxidant and hepatoprotective effects. Provides extracts such as (+)-taxifolin as an inhibitor of β-amyloid aggregation. Silymarin has been used to study:its in vitro antiviral, antibacterial, antifungal activities and cytotoxicityits effect of silymarin on bladder contractions in cyclophosphamide (CYP)-induced cystitis rat model its effect on liver toxication induced by Fumonisin B1 in mice
• Indications: Milk thistle (Silybum [Carduus] marianus) is a spiny European plant with white-veined leaves and milky sap, the seed of which is used to treat liver disease.Milk thistle seed extract is used orally in the treatment of alcoholic and other cirrhoses and in Europe intravenously for its hepatoprotective effect in Amanita and other mushroom poisonings. It is grown in this country primarily as a “liver cleanser” and is reputed to protect this organ from a wide array of toxins.Milk thistle seed contains the active principle silymarin, a complex of flavonolignan compounds including silibinin (silybin), silidianin, and silychristin.
• Clinical Use: Alcoholic cirrhosis has been improved (faster return of liver enzymes to baseline) in at least three trials, although one multicenter Spanish study failed to demonstrate any change in the clinical course.There is no evidence to support the use of milk thistle to increase alcohol tolerance, although it is certainly being used for this purpose. The effectiveness of silymarin for viral hepatitis is not clear, although several trials demonstrated enough benefit to encourage further studies. Intravenous silymarin has been demonstrated to lower mortality from Amanita mushroom poisonings, but this formulation is available only in Europe.Animal studies have demonstrated hepatic protection against alcohol, acetaminophen, and mushroom toxins and protection against hepatic fibrosis with bile duct occlusion. There is also evidence of silybin protecting against cisplatin- induced nephrotoxicity in rats. It is not yet clear whether milk thistle extract offers any renal protection to humans.

Refernces

Synthesis and antihepatotoxicity of some Wuweizisu analogues

10.1016/0223-5234(92)90148-T

The research focuses on the synthesis and antihepatotoxicity evaluation of Wuweizisu analogues. The purpose of the study is to develop new liver-protective agents by synthesizing and testing the efficacy of certain chemical compounds derived from Schisandra sinensis (Wuweizi), a traditional Chinese medicine known for its various pharmacological properties, especially its antihepatotoxic effects. The researchers synthesized a series of compounds, including dimethyl 4,4’-dimethoxy-5,6,5’,6’-dimethylenedioxybiphenyl-2,2’-dicarboxylate (VII) and 6-phenyl-3,9-dimethoxy-1,2-methylenedioxy-10,11-methylenedioxy-6,7-dihydro-5H-dibenz(c,e)azepin (X), using key chemicals such as gallic acid, dimethyl sulfate, bromine, aniline, and lithium aluminum hydride. The synthesized compounds were tested for their ability to protect against carbon tetrachloride-induced liver damage in primary cultured rat hepatocytes. The results showed that compound X exhibited superior antihepatotoxic activity compared to the known protective agents DDB and silymarin. This suggests that the synthesized compounds, particularly those with a dibenzoazepin structure, could serve as potential new liver-protective agents, offering a novel route for the development of such pharmaceuticals.

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