Conidendrin

Base Information

• Chemical Name: Conidendrin
• CAS No.: 518-55-8
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.375
• UNII: 83D6S2EBN0
• DSSTox Substance ID: DTXSID301025622,DTXSID401106144
• Nikkaji Number: J14.256E
• Wikidata: Q27138539
• Pharos Ligand ID: 47PGJYXC9438
• Metabolomics Workbench ID: 136233
• ChEMBL ID: CHEMBL463246
• Mol file: 518-55-8.mol

Synonyms:alpha-conidendrin;conidendrin

Chemical Property of Conidendrin

Chemical Property:

• Vapor Pressure: 4.65E-15mmHg at 25°C
• Melting Point: 254-255 °C
• Boiling Point: 601.4 °C at 760 mmHg
• PKA: 9.95±0.40(Predicted)
• Flash Point: 218.1 °C
• PSA: 85.22000
• Density: 1.334 g/cm³
• LogP: 2.59220
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 356.12598835
• Heavy Atom Count: 26
• Complexity: 524

Purity/Quality:

98%min ^*data from raw suppliers

(?)-α-Conidendrin ≥95.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(C3COC(=O)C3CC2=C1)C4=CC(=C(C=C4)O)OC)O
• Isomeric SMILES: COC1=C(C=C2[C@@H]([C@H]3COC(=O)[C@@H]3CC2=C1)C4=CC(=C(C=C4)O)OC)O
• Uses: (-)-ALPHA-CONIDENDRIN is a plant derived lignan that may be used as a source or reference compound to study bacteria that degrade plant lignans. (-)-ALPHA-CONIDENDRIN may be used as a starting material for the synthesis of sikkimotoxin derivatives and cytotoxic metabolites. Conidendrin is an antioxidant lignan found in trees that is also present as a component of fine particle emissions from the fireplace combustion of 6 species of woods grown in the northeastern USA.

Technology Process of Conidendrin

There total 68 articles about Conidendrin 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: 100.0%

(7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone (20268-71-7,347359-71-1) → conidendrin (518-55-8,5474-93-1,22614-13-7,26358-20-3,85699-62-3,89104-61-0,105817-20-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃;

DOI:10.1021/ol049878b

Reference yield: 97.0%

(7RS,8R,8'R)-4,4',7-trihydroxy-3,3'-dimethoxylignano-9,9'-lactone (347359-71-1) → α-conidendrin (518-55-8,5474-93-1,22614-13-7,26358-20-3,85699-62-3,89104-61-0,105817-20-7)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 80 ℃; for 0.166667h; Reagent/catalyst; Microwave irradiation;

DOI:10.1021/acs.jnatprod.6b01124

Reference yield: 94.0%

(2R,3R)-(6R,S)-(+)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide (127951-05-7,128049-88-7,128050-02-2,128050-05-5) → conidendrin (518-55-8,5474-93-1,22614-13-7,26358-20-3,85699-62-3,89104-61-0,105817-20-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 0.666667h;

DOI:10.1016/S0040-4020(01)88129-1

upstream raw materials:

(1S,3aR,4S,9aR)-1,7-dimethoxy-4-(4'-hydroxy-3'-methoxyphenyl)-1,3,3a,4,9,9a-hexahydronaphtho<2,3-c>furan-6-ol

(1R,3aR,4S,9aR)-1,7-dimethoxy-4-(4'-hydroxy-3'-methoxyphenyl)-1,3,3a,4,9,9a-hexahydronaphtho<2,3-c>furan-6-ol

(-)-O-6-Benzyl-α-conidendrine

(2R,3R)-(6R,S)-(+)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide

Downstream raw materials:

α-conidendreic acid dimethyl ester dimethyl ether

9',9'-diphenyldimethylcyclolariciresinol

9',9'-diphenyldimethylretrodendrin

C₄₀H₃₈O₆

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、 López, Martín,Simakova, Olga A.,Murzina, Elena V.,Willf?r, Stefan M.,Prosvirin, Igor,Simakov, Andrey,Murzin, Dmitry Yu.. "Gold particle size effect in biomass-derived lignan hydroxymatairesinol oxidation over Au/Al2O3 catalysts". . p. 248 - 255. Retrieved 2015/02/19.