Pinosylvin

Base Information

• Chemical Name: Pinosylvin
• CAS No.: 22139-77-1
• Molecular Formula: C14H12O2
• Molecular Weight: 212.248
• European Community (EC) Number: 683-184-0
• UNII: 881R434AIB
• ChEMBL ID: CHEMBL101506
• DSSTox Substance ID: DTXSID00895857
• Metabolomics Workbench ID: 27942
• Nikkaji Number: J10.798K,J314.538G
• NSC Number: 362430
• Wikidata: Q7196412
• Wikipedia: Pinosylvin
• Mol file: 22139-77-1.mol

Synonyms:3,5-dimethoxy-trans-stilbene;pinosylvin;pinosylvin, (E)-isomer

Chemical Property of Pinosylvin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 155.5-156°
• Refractive Index: 1.672
• Boiling Point: 397.6 °C at 760 mmHg
• PKA: 9.34±0.10(Predicted)
• Flash Point: 195 °C
• PSA: 40.46000
• Density: 1.252g/cm³
• LogP: 3.26820
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 212.083729621
• Heavy Atom Count: 16
• Complexity: 221

Purity/Quality:

Pinosylvin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-36-51/53
• Safety Statements: 26-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC2=CC(=CC(=C2)O)O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C2=CC(=CC(=C2)O)O
• Uses: Pinosylvin, a pre-infectious stilbenoid toxin, is used to study its properties as a fungitoxin and therapeutic agent. Pinosylvin is used as a representative stilbene to study its biological actions and therapeutic value in processes such as cell survival, apoptosis and cell mobility.

Technology Process of Pinosylvin

There total 37 articles about Pinosylvin 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: 99.0%

5-[(1Z)-2-phenylethenyl]benzene-1,3-diol (106325-78-4) → pinosylvin (22139-77-1)

Guidance literature:

With diphenyldisulfane; In tetrahydrofuran; for 0.5h; Heating;

DOI:10.1248/cpb.40.2842

Reference yield: 90.0%

(E)-1-<3,5-bis(benzyloxy)phenyl>-2-phenylethene (133156-35-1) → pinosylvin (22139-77-1)

Guidance literature:

With hydrogen; In dichloromethane; at 20 ℃; for 5h; under 3750.38 Torr;

Reference yield: 85.0%

(E)-3,5-dimethoxystilbene (21956-56-9) → pinosylvin (22139-77-1)

Guidance literature:

With pyridine hydrochloride; at 190 ℃; for 4h;

DOI:10.1055/s-2008-1078487

upstream raw materials:

3-methoxy-5-[(E)-2-phenylvinyl]phenol

(E)-3,5-dimethoxystilbene

(E)-1-<3,5-bis(benzyloxy)phenyl>-2-phenylethene

5-[(1Z)-2-phenylethenyl]benzene-1,3-diol

Downstream raw materials:

2,3-dihydro-2,2-dimethyl-7-hydroxy-5-(2-phenylethenyl)-4H-1-benzopyran-4-one

2,3-dihydro-2,2-dimethyl-5-hydroxy-7-(2-phenylethenyl)-4H-1-benzopyran-4-one

(E)-3-hydroxy-5-hexyloxystilbene

(E)-3-hydroxy-5-propoxystilbene

Refernces

• 1、 Baumann, Andreas N.,Dechent, Jonas,Didier, Dorian,Jagau, Thomas C.,Müller, Nicolas,Music, Arif. "Electro-Olefination—A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes". supporting information. . Retrieved 2020/07/04.
• 2、 Yang., Jinfei,Wang, Chengniu,Sun, Yufeng,Man, Xuyan,Li, Jinxia,Sun, Fei. "Ligand-controlled iridium-catalyzed semihydrogenation of alkynes with ethanol: highly stereoselective synthesis of E- and Z-alkenes". supporting information. p. 1903 - 1906. Retrieved 2019/05/02.