Phillyrin

Base Information

• Chemical Name: Phillyrin
• CAS No.: 487-41-2
• Molecular Formula: C27H34O11
• Molecular Weight: 534.56
• Hs Code.: 29389090
• UNII: VE9P4964MG
• DSSTox Substance ID: DTXSID40197589
• Nikkaji Number: J324.135A
• Wikipedia: Phillyrin
• Wikidata: Q27151384
• Mol file: 487-41-2.mol

Synonyms:4-(4-(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-2-methoxyphenyl, (1S-(1alpha,3aalpha,4beta,6aalpha))-beta-D-glucopyranoside;forsythin;phillyrin

Chemical Property of Phillyrin

Chemical Property:

• Vapor Pressure: 2.14E-22mmHg at 25°C
• Melting Point: approximate 157℃
• Refractive Index: 1.596
• Boiling Point: 730.4 °C at 760 mmHg
• PKA: 12.81±0.70(Predicted)
• Flash Point: 395.5 °C
• PSA: 145.53000
• Density: 1.361 g/cm³
• LogP: 0.96630
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 534.21011190
• Heavy Atom Count: 38
• Complexity: 757

Purity/Quality:

1%, ^*data from raw suppliers

Phillyrin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)OC)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)OC)OC
• Uses: Phillyrin is a natural lignan compound attenuating tumor necrosis factor secreted from macrophages, that play an inportant role in adipocyte dysfunctions. Anti-obesity.

Technology Process of Phillyrin

There total 2 articles about Phillyrin 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: 79.8%

tetraacyl forsythin → phillyrin (487-41-2)

Guidance literature:

With sodium methylate; acetic acid; In methanol; dichloromethane; for 4h; pH=6;

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (3R,4S,5S,6R)-2-{4-[(1S,3aR,4S,6aR)-4-(4-Hydroxy-3-methoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-yl]-2-methoxy-phenoxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (24404-49-7,41607-20-9,69251-96-3,74983-66-7) → (3R,4S,5S,6R)-2-{4-[(1S,3aR,4S,6aR)-4-(3,4-Dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-yl]-2-methoxy-phenoxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (487-41-2,41607-21-0,74957-57-6)

Guidance literature:

Reference yield:

phillyrin (487-41-2) → phillygenin (487-39-8)

Guidance literature:

With thymol; emulsin; In water; at 38 ℃; for 72h;

DOI:10.1016/S0031-9422(00)81293-5

upstream raw materials:

diazomethane

(3R,4S,5S,6R)-2-{4-[(1S,3aR,4S,6aR)-4-(4-Hydroxy-3-methoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-yl]-2-methoxy-phenoxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

(+)-pinoresinol monomethyl ether

phillygenin

Refernces

• 1、 Nishibe, Sansei,Tsukamoto, Hiroki,Hisada, Sueo. "Effects of O-Methylation and O-Glucosylation on Carbon-13 Nuclear Magnetic Resonance Chemical Shifts of Matairesinol, (+)-Pinoresinol and (+)-Epipinoresinol". . p. 4653 - 4657. Retrieved 2007/10/02.