Yatein

Base Information

• Chemical Name: Yatein
• CAS No.: 40456-50-6
• Molecular Formula: C₂₂H₂₄O₇
• Molecular Weight: 400.428
• DSSTox Substance ID: DTXSID50193471
• Nikkaji Number: J257.868I
• Wikidata: Q27106408
• Pharos Ligand ID: ZKN43CPQVX8A
• Metabolomics Workbench ID: 69460
• ChEMBL ID: CHEMBL471067
• Mol file: 40456-50-6.mol

Synonyms:yatein

Chemical Property of Yatein

Chemical Property:

• Vapor Pressure: 8.82E-13mmHg at 25°C
• Boiling Point: 564.9°Cat760mmHg
• Flash Point: 246.2°C
• PSA: 72.45000
• Density: 1.266g/cm³
• LogP: 3.01550
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 400.15220310
• Heavy Atom Count: 29
• Complexity: 541

Purity/Quality:

Analysis control,HPLC≥96.5% ^*data from raw suppliers

Yatein 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)CC2C(COC2=O)CC3=CC4=C(C=C3)OCO4
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)C[C@@H]2[C@H](COC2=O)CC3=CC4=C(C=C3)OCO4
• Description: Yatein is a lignan that has been found in C. formosana and has diverse biological activities. It inhibits the cytochrome P450 (CYP) isoform CYP3A4 (IC50 = 1 μM). Yatein inhibits herpes simplex virus 1 (HSV-1) replication in a plaque reduction assay (IC50 = 30.6 μM). It induces apoptosis and production of reactive oxygen species (ROS) in, and is cytotoxic to, A549 and CL1-5 non-small cell lung cancer (NSCLC) cells (IC50s = 3.5 and 1.9 μM, respectively). Yatein inhibits aggregation of rabbit platelets induced by platelet-activating factor (PAF), collagen, or arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) in a concentration-dependent manner.

Technology Process of Yatein

There total 81 articles about Yatein 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: 95.0%

(3S,4S)-(+)-2-hydroxy-3-(3',4',5'-trimethoxybenzyl)-4-piperonyl-tetrahydrofurane (72627-54-4,86992-94-1) → yatein (40456-50-6,17301-91-6,61091-56-3,72690-16-5,96745-44-7,119066-80-7,128049-89-8,139560-31-9)

Guidance literature:

With Collins oxidation agent; In dichloromethane; for 1.33333h; Ambient temperature;

DOI:10.1016/S0040-4020(01)82416-9

Reference yield: 95.0%

rac-4-{benzo[d][1,3]dioxol-5-yl(hydroxy)methyl}-3-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one → (3R*,4R*)-3-(3,4,5-trimethoxybenzyl)-4-(3,4-methylenedioxybenzyl)-4,5-dihydro-2(3H)-furanone (17301-91-6,40456-50-6,61091-56-3,72690-16-5,96745-44-7,119066-80-7,128049-89-8,139560-31-9)

Guidance literature:

With perchloric acid; palladium on activated carbon; hydrogen; In methanol; for 16h;

DOI:10.1002/anie.201900926

Reference yield: 85.0%

(R)-(+)-3-piperonyl-4-butanolide (17187-77-8) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) → yatein (40456-50-6,17301-91-6,61091-56-3,72690-16-5,96745-44-7,119066-80-7,128049-89-8,139560-31-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 1.) -78 deg C, 2 h, 2.) 1 h;

DOI:10.1021/jo00073a034

upstream raw materials:

4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one

3,4,5-trimethoxybenzyl bromide

(E)-3-(benzo[d][1,3]dioxol-5-yl)allyl 2-bromo-3-(3,4,5-trimethoxyphenyl)propanoate

rac-(7'β,8β,8'α)-7-hydroxy-3',4',5'-trimethoxy-3,4-methylenedioxylignan-9',9-olides

Downstream raw materials:

rac-(7'β,8α,8'percentb)-3',4',5'-trimethoxy-4,5-methylenedioxy-2,7'-cyclolignan-9',9-olide

rac-(8α,8'β)-4'-hydroxy-3',5'-dimethoxy-3,4-methylenedioxylignan-9',9-olide

(3S,4S)-4-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one

yatein

Refernces

• 1、 Hartmann, Peter,Lazzarotto, Mattia,Steiner, Lorenz,Cigan, Emmanuel,Poschenrieder, Silvan,Sagmeister, Peter,Fuchs, Michael. "TRIP-Catalyzed Asymmetric Synthesis of (+)-Yatein, (-)-α-Conidendrin, (+)-Isostegane, and (+)-Neoisostegane". . p. 5831 - 5837. Retrieved 2019/04/25.
• 2、 Kc, Shekhar,Basnet, Prakash,Thapa, Surendra,Shrestha, Bijay,Giri, Ramesh. "Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products". . p. 2920 - 2936. Retrieved 2018/03/09.