Silychrystin

Base Information

• Chemical Name: Silychrystin
• CAS No.: 33889-69-9
• Molecular Formula: C₂₅H₂₂O₁₀
• Molecular Weight: 482.444
• DSSTox Substance ID: DTXSID60865692
• Wikidata: Q104938448
• Mol file: 33889-69-9.mol

Synonyms:Silychrystin;Silymarin II;Silicristin, INN;SCHEMBL10049339;DTXSID60865692;BCP07563;Silychristin;Silicristina;Silicristine;FT-0630575;Q-100411;B0005-464841;3,5,7-Trihydroxy-2-[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4H-1-benzopyran-4-one

Chemical Property of Silychrystin

Chemical Property:

• Vapor Pressure: 9.44E-26mmHg at 25°C
• Melting Point: 174～176℃
• Boiling Point: 782oC at 760 mmHg
• PKA: 7.39±0.60(Predicted)
• Flash Point: 270.5oC
• PSA: 166.14000
• Density: 1.578g/cm3
• LogP: 2.40450
• Storage Temp.: 2-8°C
• Solubility.: Acetone (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 482.12129689
• Heavy Atom Count: 35
• Complexity: 765

Purity/Quality:

97% ^*data from raw suppliers

Silychristin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2C(C3=C(O2)C(=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)O)CO)O
• Uses: Silychristin is a new natural product has been isolated from silymarin, the hepatoprotective extract of milk thistle (Silybum marianum) fruits. Silychristin has been shown to be an antihepatotoxic fla vonolignan. Silychristin is a new natural product has been isolated from silymarin, the hepatoprotective extract of milk thistle (Silybum marianum) fruits. Silychristin has been shown to be an antihepatotoxic flavonolignan.

Technology Process of Silychrystin

There total 36 articles about Silychrystin 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: 19.0%

{3-[(2S,3R)-7-Methoxymethoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-3-methoxymethoxymethyl-2,3-dihydro-benzofuran-5-yl]-oxiranyl}-(2,4,6-tris-methoxymethoxy-phenyl)-methanone (119384-71-3,124815-78-7) → (+/-)-silychristin (33889-69-9,119435-01-7,125762-44-9,879325-58-3) + (2R,3R)-3,5,7-Trihydroxy-2-[(2S,3R)-7-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-hydroxymethyl-2,3-dihydro-benzofuran-5-yl]-chroman-4-one (33889-69-9,119435-01-7,125762-44-9,879325-58-3)

Guidance literature:

With hydrogenchloride; In methanol; at 70 ℃; for 0.25h;

DOI:10.1248/cpb.37.1441

Reference yield: 19.0%

{3-[(2S,3R)-7-Methoxymethoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-3-methoxymethoxymethyl-2,3-dihydro-benzofuran-5-yl]-oxiranyl}-(2,4,6-tris-methoxymethoxy-phenyl)-methanone (119384-71-3,124815-78-7) → (+/-)-silychristin (33889-69-9,119435-01-7,125762-44-9,879325-58-3) + (2R,3R)-3,5,7-Trihydroxy-2-[(2S,3R)-7-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-hydroxymethyl-2,3-dihydro-benzofuran-5-yl]-chroman-4-one (33889-69-9,119435-01-7,125762-44-9,879325-58-3)

Guidance literature:

With hydrogenchloride; In methanol; at 70 ℃; for 0.25h;

DOI:10.1248/cpb.37.1441

Reference yield:

4-benzyloxy-3-methoxyacetophenone (1835-11-6) → (+/-)-silychristin (33889-69-9,119435-01-7,125762-44-9,879325-58-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 93 percent / KOH / ethanol

2: 87 percent / conc. HCl / methanol; dioxane

3: 92 percent / 30percent H₂O₂, 5percent NaOH / methanol; dioxane

4: 1.) BF₃*Et₂O, 2.) NaBH₄ / 1.) benzene, 0 deg C, 2.) THF

5: 66 percent / H₂ / 10percent Pd-C / methanol

6: BF₃-Et₂O / 5 °C

7: 66 percent / (i-Pr)2NEt / CH₂Cl₂

8: 91 percent / 1M NaOH / methanol

9: 95 percent / MnO₂ / CH₂Cl₂

10: 94 percent / NaOH / ethanol

11: 96 percent / 30percent H₂O₂, 5percent NaOH / methanol

12: 19 percent / conc. HCl / methanol / 70 °C

With hydrogenchloride; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane;

DOI:10.1039/c39880000749

upstream raw materials:

{3-[(2S,3R)-7-Methoxymethoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-3-methoxymethoxymethyl-2,3-dihydro-benzofuran-5-yl]-oxiranyl}-(2,4,6-tris-methoxymethoxy-phenyl)-methanone

4-benzyloxy-3-methoxyacetophenone

erythro-1-(4-hydroxy-3-methoxyphenyl)-2-(2,3-dihydroxy-5-hydroxymethylphenyl)-1,3-propanediol

3-hydroxymethyl-2-(4-hydroxy-3-methoxyphenyl)-7-hydroxy-5-acetoxymethyl-2,3-dihydrobenzofuran

Downstream raw materials:

isohydnocarpin

2,3-dehydrosilychristin A