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Rheic Acid;Rhubarb yellow;Monorhein

Base Information
  • Chemical Name:Rheic Acid;Rhubarb yellow;Monorhein
  • CAS No.:76-66-4
  • Molecular Formula:C22H28N2O4
  • Molecular Weight:384.475
  • Hs Code.:29399990
  • European Community (EC) Number:683-092-0
  • ChEMBL ID:CHEMBL1668786
  • Metabolomics Workbench ID:70231
  • Nikkaji Number:J9.110C
  • Wikipedia:Rhynchophylline
  • Mol file:76-66-4.mol
Rheic Acid;Rhubarb yellow;Monorhein

Synonyms:isorhynchophylline;isorhyncophylline;rhynchophylline;rhyncophylline;rhyncophylline, (16E)-isomer;rhyncophylline, (16E,20alpha)-isomer

Suppliers and Price of Rheic Acid;Rhubarb yellow;Monorhein
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • Usbiological
  • Rhynchophylline
  • 20mg
  • $ 433.00
  • TRC
  • Rhynchophylline
  • 100 mg
  • $ 315.00
  • Medical Isotopes, Inc.
  • Rhynchophylline
  • 10 mg
  • $ 620.00
  • Labseeker
  • RHYNCHOLPHYLLINE 99
  • 1g
  • $ 1083.00
  • DC Chemicals
  • Rhynchophylline >98%,StandardReferencesGrade
  • 1 g
  • $ 1900.00
  • DC Chemicals
  • Rhynchophylline >98%,StandardReferencesGrade
  • 250 mg
  • $ 650.00
  • Crysdot
  • Rhynchophylline 98+%
  • 5mg
  • $ 49.00
  • Crysdot
  • Rhynchophylline 98+%
  • 10mg
  • $ 77.00
  • ChemScene
  • Rhynchophylline 98.51%
  • 10mg
  • $ 174.00
  • ChemScene
  • Rhynchophylline 98.51%
  • 5mg
  • $ 96.00
Total 96 raw suppliers
Chemical Property of Rheic Acid;Rhubarb yellow;Monorhein
Chemical Property:
  • Appearance/Colour:Red brown or white fine powder 
  • Vapor Pressure:1.32E-12mmHg at 25°C 
  • Melting Point:216°; mp 197-199° (Ban et al., loc. cit.) 
  • Refractive Index:1.596 
  • Boiling Point:560.8 °C at 760 mmHg 
  • PKA:6.4(at 25℃) 
  • Flash Point:293 °C 
  • PSA:67.87000 
  • Density:1.23 g/cm3 
  • LogP:2.77610 
  • Storage Temp.:0-10°C 
  • Solubility.:Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) 
  • XLogP3:2.3
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:5
  • Rotatable Bond Count:5
  • Exact Mass:384.20490738
  • Heavy Atom Count:28
  • Complexity:663
Purity/Quality:

≥98% *data from raw suppliers

Rhynchophylline *data from reagent suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes: 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:CCC1CN2CCC3(C2CC1C(=COC)C(=O)OC)C4=CC=CC=C4NC3=O
  • Isomeric SMILES:CC[C@H]1CN2CC[C@]3([C@@H]2C[C@@H]1/C(=C/OC)/C(=O)OC)C4=CC=CC=C4NC3=O
  • Uses Rhynchophylline is a novel erythropoietin-producing hepatocellular A4 (EphA4) inhibitor.
Technology Process of Rheic Acid;Rhubarb yellow;Monorhein

There total 16 articles about Rheic Acid;Rhubarb yellow;Monorhein 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:
Guidance literature:
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 18h; under 760.051 Torr;
DOI:10.1002/ejoc.201201505
Guidance literature:
Multi-step reaction with 6 steps
1.1: thiophenol; potassium carbonate / dimethyl sulfoxide / 2.15 h
2.1: triethylamine / acetonitrile / 2.33 h / 20 °C
3.1: caesium carbonate; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; bis(η3-allyl-μ-chloropalladium(II)) / tetrahydrofuran / 8 h / Inert atmosphere
4.1: 6 h / 0 °C
5.1: tetrahydrofuran / 0.08 h / 20 °C
5.2: -78 - 20 °C
5.3: 20 h / 20 °C
6.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 18 h / 760.05 Torr
With bis(η3-allyl-μ-chloropalladium(II)); palladium 10% on activated carbon; hydrogen; potassium carbonate; caesium carbonate; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; dimethyl sulfoxide; ethyl acetate; acetonitrile; 5.2: |Wittig Olefination;
DOI:10.1002/ejoc.201201505
Guidance literature:
Multi-step reaction with 5 steps
1.1: triethylamine / acetonitrile / 2.33 h / 20 °C
2.1: caesium carbonate; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; bis(η3-allyl-μ-chloropalladium(II)) / tetrahydrofuran / 8 h / Inert atmosphere
3.1: 6 h / 0 °C
4.1: tetrahydrofuran / 0.08 h / 20 °C
4.2: -78 - 20 °C
4.3: 20 h / 20 °C
5.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 18 h / 760.05 Torr
With bis(η3-allyl-μ-chloropalladium(II)); palladium 10% on activated carbon; hydrogen; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; ethyl acetate; acetonitrile; 4.2: |Wittig Olefination;
DOI:10.1002/ejoc.201201505
Refernces

Synthesis and structure-activity relationship study of antidiabetic penta-O-galloyl-D-glucopyranose and its analogues

10.1021/jm060087k

The research investigates the antidiabetic properties of penta-O-galloyl-D-glucopyranose (PGG) and its analogues. The study explores the structure-activity relationship of PGG's R- and α-anomers, which act as insulin mimetics, stimulating glucose transport in adipocytes and reducing blood glucose and insulin levels in diabetic and obese animals. The researchers synthesized and tested various novel compounds, finding that both the glucose core and the galloyl groups are crucial for activity. The galloyl groups linked to positions 1, 2, 3, and 4 of glucose are essential, while the one at position 6 is not. Notably, 6-chloro-6-deoxy-1,2,3,4-tetra-O-galloyl-R-D-glucopyranose (80) exhibited significantly higher glucose transport stimulatory activity than PGG, comparable to insulin. Key chemicals used in the research include PGG, gallic acid, methyl galloate, ellagic acid, and various derivatives of glucose and galloyl groups. The study provides insights into the development of new antidiabetic therapeutics that can address both hyperglycemia and adiposity.

Studies on plants containing indole alkaloids. VIII. Indole alkaloid glycosides and other constituents of the leaves of Uncaria rhynchophylla Miq

10.1248/cpb.30.4046

This study investigated the glycosides and other polar components of Uncaria rhynchophylla, a plant used in traditional Chinese medicine. The researchers isolated a new glycoalkaloid named rhynchophylline (IV), which was identified as 6'-feruloylvinblastine lactam. They achieved a partial synthesis of rhynchophylline using vinblastine lactam as a starting material. In addition, they isolated five new compounds from the plant: valerine, vinblastine lactam, isofructoside, hyperoside, and trilobite. The study focused on the extraction and characterization of these compounds, using techniques such as UV spectroscopy, H-NMR, and 13C-NMR to elucidate their structures. These findings help understand the chemical composition of Uncaria rhynchophylla, which may have implications for its medicinal applications.

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