Silybin

Base Information

• Chemical Name: Silybin
• CAS No.: 36804-17-8
• Molecular Formula: C₂₅H₂₂O₁₀
• Molecular Weight: 482.444
• 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: 36804-17-8.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:

• Vapor Pressure: 1.63E-26mmHg at 25°C
• Melting Point: 160 °C
• Boiling Point: 793°C at 760 mmHg
• PKA: 7.39±0.60(Predicted)
• Flash Point: 274.4°C
• PSA: 159.05000
• Density: 1.527g/cm³
• LogP: 3.38430
• Storage Temp.: Freezer
• 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%,99%, ^*data from raw suppliers

Silybin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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.

Technology Process of Silybin

There total 11 articles about Silybin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

{3-[(2R,3R)-2-Hydroxymethyl-3-(3-methoxy-4-methoxymethoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-oxiranyl}-(2,4,6-tris-methoxymethoxy-phenyl)-methanone (98314-88-6) → (+/-)-silybin (22888-70-6,36804-17-8,87725-91-5,142796-20-1,142797-34-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; at 70 ℃; for 0.0833333h;

DOI:10.1248/cpb.33.1419

Reference yield:

4-hydroxy-3-(methoxymethoxy)benzaldehyde (65298-98-8) → (+/-)-silybin (22888-70-6,36804-17-8,87725-91-5,142796-20-1,142797-34-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 66 percent / tert-BuOK / dimethylformamide / 3 h / Ambient temperature

2: 94 percent / NH₄Cl / methanol / 1 h / Heating

3: 97 percent / NaBH₄ / ethanol / 8 h / Ambient temperature

4: 70 percent / sulfuric acid (5percent) / acetic acid / 0.5 h / 70 °C

5: 63 percent / H₂ / Pd-C (5percent) / ethyl acetate; ethanol / Ambient temperature

6: 79 percent / NaH / tetrahydrofuran; paraffin / 2 h / Ambient temperature

7: 94 percent / NaOH / ethanol / 8 h

8: 97 percent / H₂O₂ (30percent), NaOH (5percent) / H₂O; methanol / 4 h / Ambient temperature

9: 63 percent / concd. HCl / methanol; tetrahydrofuran / 0.08 h / 70 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; potassium tert-butylate; hydrogen; dihydrogen peroxide; sodium hydride; ammonium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; paraffin;

DOI:10.1248/cpb.33.1419

Reference yield:

ethyl 2-bromo-3-(4-benzyloxy-3-methoxyphenyl)-3-oxopropionate (7572-90-9) → (+/-)-silybin (22888-70-6,36804-17-8,87725-91-5,142796-20-1,142797-34-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 66 percent / tert-BuOK / dimethylformamide / 3 h / Ambient temperature

2: 94 percent / NH₄Cl / methanol / 1 h / Heating

3: 97 percent / NaBH₄ / ethanol / 8 h / Ambient temperature

4: 70 percent / sulfuric acid (5percent) / acetic acid / 0.5 h / 70 °C

5: 63 percent / H₂ / Pd-C (5percent) / ethyl acetate; ethanol / Ambient temperature

6: 79 percent / NaH / tetrahydrofuran; paraffin / 2 h / Ambient temperature

7: 94 percent / NaOH / ethanol / 8 h

8: 97 percent / H₂O₂ (30percent), NaOH (5percent) / H₂O; methanol / 4 h / Ambient temperature

9: 63 percent / concd. HCl / methanol; tetrahydrofuran / 0.08 h / 70 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; potassium tert-butylate; hydrogen; dihydrogen peroxide; sodium hydride; ammonium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; paraffin;

DOI:10.1248/cpb.33.1419

upstream raw materials:

coniferol

taxifolin

{3-[(2R,3R)-2-Hydroxymethyl-3-(3-methoxy-4-methoxymethoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-oxiranyl}-(2,4,6-tris-methoxymethoxy-phenyl)-methanone

4-hydroxy-3-(methoxymethoxy)benzaldehyde

Refernces

• 1、 Merlini, Lucio,Zanarotti, Antonio,Pelter, Andrew,Rochefort, Malcolm P.,Haensel, Rudolf. "Benzodioxans by Oxidative Phenol Coupling. Synthesis of Silybin". . p. 775 - 778. Retrieved 2007/10/02.