Medicarpin

Base Information

• Chemical Name: Medicarpin
• CAS No.: 32383-76-9
• Molecular Formula: C16H14O4
• Molecular Weight: 270.285
• NSC Number: 350085
• UNII: 6TX086I6IG
• DSSTox Substance ID: DTXSID301026587
• Nikkaji Number: J92.506C
• Wikipedia: Medicarpin
• Wikidata: Q56036865
• Metabolomics Workbench ID: 22754
• ChEMBL ID: CHEMBL238845
• Mol file: 32383-76-9.mol

Synonyms:6a,11a-dihydro-9-methoxy-6H-benzofuro(3,2-c)(1)benzopyran-3-ol;medicarpin;medicarpin, (6aS-cis)-isomer;medicarpin, (cis-(+-))-isomer

Chemical Property of Medicarpin

Chemical Property:

• Vapor Pressure: 1.31E-07mmHg at 25°C
• Melting Point: 127.5-128.5°
• Refractive Index: 1.629
• Boiling Point: 418.8 °C at 760 mmHg
• PKA: 9.50±0.20(Predicted)
• Flash Point: 207.1 °C
• PSA: 47.92000
• Density: 1.319 g/cm³
• LogP: 3.01050
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 270.08920892
• Heavy Atom Count: 20
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

Medicarpin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)C3COC4=C(C3O2)C=CC(=C4)O
• Isomeric SMILES: COC1=CC2=C(C=C1)[C@@H]3COC4=C([C@@H]3O2)C=CC(=C4)O
• Uses: Medicarpin can be used to inhibit IL-8 release via interactions with toll-like receptor 4 and lipopolysaccharide. It can also be used to treat COVID-19.

Technology Process of Medicarpin

There total 25 articles about Medicarpin 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:

C30H28O4 → medicarpin (32383-76-9) + medicarpin (33983-39-0)

Guidance literature:

C₃₀H₂₈O₄; With lead(II,IV) oxide; acetic acid; In benzene; at 85 ℃; for 3h;

With 10 wt% Pd(OH)2 on carbon; hydrogen; In tetrahydrofuran; ethanol; at 20 ℃;

With potassium carbonate; In ethyl acetate; at 20 ℃; Overall yield = 49 %; Overall yield = 13 mg; enantioselective reaction;

DOI:10.1016/j.tetlet.2018.05.016

Reference yield:

C18H18O6 → medicarpin (32383-76-9)

Guidance literature:

With potassium carbonate; In ethyl acetate; at 20 ℃; for 5h;

DOI:10.1002/anie.201408910

Reference yield:

(2R,3S)-2,7,4'-trihydroxyisoflavanone (131887-80-4) → medicarpin (32383-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2-methoxyethanol / 2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase

2: 2-hydroxyisoflavanone dehydratase

With 2-methoxy-ethanol; 2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase; 2-hydroxyisoflavanone dehydratase;

DOI:10.1016/j.phytochem.2006.09.010

upstream raw materials:

7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on

2,7-dihydroxy-4'-methoxyisoflavanone

(2R,3S)-2,7,4'-trihydroxyisoflavanone

3-(2,4-dimethoxyphenyl)-7-hydroxy-4H-chromen-4-one

Downstream raw materials:

medicarpin

medicarpin 3-O-glucoside

3-hydroxy-9-methoxy-6H-benzofuro[3,2-c]chromen-6-one

Refernces

• 1、 Zhang, Jian,Zhang, Shuangzhan,Yang, Huixin,Zhou, Ding,Yu, Xueting,Wang, Wei,Xie, Hexin. "A general asymmetric route to enantio-enriched isoflavanes via an organocatalytic annulation of o-quinone methides and aldehydes". . p. 2407 - 2411. Retrieved 2018/05/24.
• 2、 Goel, Atul,Kumar, Amit,Hemberger, Yasmin,Raghuvanshi, Ashutosh,Jeet, Ram,Tiwari, Govind,Knauer, Michael,Kureel, Jyoti,Singh, Anuj K.,Gautam, Abnish,Trivedi, Ritu,Singh, Divya,Bringmann, Gerhard. "Synthesis, optical resolution, absolute configuration, and osteogenic activity of cis-pterocarpans". . p. 9583 - 9592. Retrieved 2013/01/16.