33983-40-3

Basic information

• Product Name: MEDICARPIN
• Synonyms: MEDICARPIN;3-HYDROXY-9-METHOXYPTEROCARPAN;(+)-Demethylhomopterocarpin;(6aS,11aS)-6a,11a-Dihydro-9-methoxy-6H-benzofuro[3,2-c][1]benzopyran-3-ol;[6aS,(+)]-6aβ,11aβ-Dihydro-9-methoxy-6H-benzofuro[3,2-c][1]benzopyran-3-ol;C01729
• CAS NO: 33983-40-3
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.28
• Mol File: 33983-40-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 418.8 ºC at 760 mmHg
• Flash Point: 207.1 ºC
• Appearance: /
• Density: 1.319 g/cm³
• Vapor Pressure: 1.31E-07mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: MEDICARPIN(CAS DataBase Reference)
• NIST Chemistry Reference: MEDICARPIN(33983-40-3)
• EPA Substance Registry System: MEDICARPIN(33983-40-3)

Safety Data

• Hazardous Substances Data: 33983-40-3(Hazardous Substances Data)

Usage

Definition

ChEBI: The (+)-enantiomer of medicarpin.

InChI:InChI=1/C16H14O4/c1-18-10-3-5-11-13-8-19-14-6-9(17)2-4-12(14)16(13)20-15(11)7-10/h2-7,13,16-17H,8H2,1H3/t13-,16-/m1/s1

Upstream product

• 6496-89-5 2,4-dimethoxyphenylacetic acid 
• 108-46-3 recorcinol 
• 1890-99-9 7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one 
• 1891-01-6 3-(2,4-dimethoxyphenyl)-7-hydroxy-4H-chromen-4-one 

Downstream Products

• 32383-76-9 medicarpin 
• 33983-39-0 medicarpin 
• 1690-62-6 3-hydroxy-9-methoxy-6H-benzofuro[3,2-c]chromen-6-one 

Relevant articles and documents

Synthesis, optical resolution, absolute configuration, and osteogenic activity of cis-pterocarpans

A convenient synthesis of natural and synthetic pterocarpans was achieved in three steps. Optical resolution of the respective enantiomers was accomplished by analytical and semi-preparative HPLC on a chiral stationary phase. For medicarpin and its synthetic derivative 9-demethoxymedicarpin, the absolute configuration was confirmed by a combination of experimental LC-ECD coupling and quantum-chemical ECD calculations. (-)-Medicarpin and (-)-9-demethoxymedicarpin are both 6aR,11aR-configured, and consequently the corresponding enantiomers, (+)-medicarpin and (+)-9-demethoxymedicarpin, possess the 6aS,11aS-configuration. A comparative mechanism study for osteogenic (bone forming) activity of medicarpin (racemic versus enantiomerically pure material) revealed that (+)-(6aS,11aS)-medicarpin (6a) significantly increased the bone morphogenetic protein-2 (BMP2) expression and the level of the bone-specific transcription factor Runx-2 mRNA, while the effect was opposite for the other enantiomer, (-)-(6aR,11aR)-medicarpin (6a), and for the racemate, (±)-medicarpin, the combined effect of both the enantiomers on transcription levels was observed. The Royal Society of Chemistry 2012.