CAS No.32383-76-9,Medicarpin Suppliers

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Basic Information

Molecular Structure:
CAS No.:	32383-76-9
Name:	Medicarpin
Article Data:	5

Formula:	C₁₆H₁₄O₄
Molecular Weight:	270.285
Synonyms:	(-)-3-Hydroxy-9-methoxypterocarpan;(-) Medicarpin;
Density:	1.319 g/cm³
Melting Point:	127.5-128.5°
Boiling Point:	418.8 °C at 760 mmHg
Flash Point:	207.1 °C
PSA:	47.92000
LogP:	3.01050

Synthetic route

: 485-72-3
7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on

: 32383-76-9
medicarpin

: 770722-02-6
2,7-dihydroxy-4'-methoxyisoflavanone

: 32383-76-9
medicarpin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2-hydroxyisoflavanone dehydratase View Scheme

: 131887-80-4
(2R,3S)-2,7,4'-trihydroxyisoflavanone

: 32383-76-9
medicarpin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 2-methoxyethanol / 2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase 2: 2-hydroxyisoflavanone dehydratase View Scheme

: 1891-01-6
3-(2,4-dimethoxyphenyl)-7-hydroxy-4H-chromen-4-one

A: 32383-76-9
medicarpin

B: 33983-39-0
medicarpin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / acetonitrile / 0 °C / Reflux 1.2: Cooling with ice 2.1: sodium tetrahydroborate / ethanol / 0 - 20 °C 3.1: Lux cellulose-1 PHENOMENIX column / acetonitrile; water / Resolution of racemate View Scheme

: 1890-99-9
7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

A: 32383-76-9
medicarpin

B: 33983-39-0
medicarpin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 0 - 20 °C 2: Lux cellulose-1 PHENOMENIX column / acetonitrile; water / Resolution of racemate View Scheme

: 108-46-3
recorcinol

A: 32383-76-9
medicarpin

B: 33983-39-0
medicarpin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: boron trifluoride diethyl etherate / 2 h / 90 - 100 °C 1.2: 50 - 90 °C 2.1: aluminum (III) chloride / acetonitrile / 0 °C / Reflux 2.2: Cooling with ice 3.1: sodium tetrahydroborate / ethanol / 0 - 20 °C 4.1: Lux cellulose-1 PHENOMENIX column / acetonitrile; water / Resolution of racemate View Scheme

: 32383-76-9, 33983-39-0, 33983-40-3, 57458-34-1
9-methoxy-6a,11a-dihydro-6H-benzo[4,5]furo[3,2-c]chromen-3-ol

A: 32383-76-9
medicarpin

B: 33983-39-0
medicarpin

Conditions

Conditions	Yield
With Lux cellulose-1 PHENOMENIX column In water; acetonitrile Resolution of racemate;	A n/a B n/a

: 6496-89-5
2,4-dimethoxyphenylacetic acid

A: 32383-76-9
medicarpin

B: 33983-39-0
medicarpin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: boron trifluoride diethyl etherate / 2 h / 90 - 100 °C 1.2: 50 - 90 °C 2.1: aluminum (III) chloride / acetonitrile / 0 °C / Reflux 2.2: Cooling with ice 3.1: sodium tetrahydroborate / ethanol / 0 - 20 °C 4.1: Lux cellulose-1 PHENOMENIX column / acetonitrile; water / Resolution of racemate View Scheme

: (2S,3R)-3-(2-hydroxy-4-methoxyphenyl)-2-(((1R,2S)-2-phenylcyclohexyl)oxy)chroman-7-ol

: 32383-76-9
medicarpin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydride / N,N-dimethyl-formamide / 5 h / -78 - 20 °C / Inert atmosphere 2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2.17 h / -78 °C 3: lead(II,IV) oxide / benzene / 3 h / 85 °C 4: palladium 10% on activated carbon; hydrogen / ethanol 5: potassium carbonate / ethyl acetate / 5 h / 20 °C View Scheme

: (2S,3R)-7-(benzyloxy)-3-(2-(benzyloxy)-4-methoxyphenyl)-2-(((1R,2S)-2-phenylcyclohexyl)oxy)chroman

: 32383-76-9
medicarpin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2.17 h / -78 °C 2: lead(II,IV) oxide / benzene / 3 h / 85 °C 3: palladium 10% on activated carbon; hydrogen / ethanol 4: potassium carbonate / ethyl acetate / 5 h / 20 °C View Scheme

Raw Materials

108-46-3

485-72-3

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Specification

The Medicarpin, with the CAS registry number 32383-76-9, is also known as (-)-3-Hydroxy-9-methoxypterocarpan. This chemical's molecular formula is C₁₆H₁₄O₄ and molecular weight is 270.28. What's more, its IUPAC name is (6aR, 11aR)-9-Methoxy-6a, 11a-dihydro-6H-[1]benzofuro[3, 2-c]chromen-3-ol. In addition, Medicarpin is a pterocarpan, a derivative of isoflavonoids, found in Medicago truncatula.

Physical properties about Medicarpin are: (1)ACD/LogP: 2.72; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 4; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 2; (6)Polar Surface Area: 36.92 Å²; (7)Index of Refraction: 1.629; (8)Molar Refractivity: 72.84 cm³; (9)Molar Volume: 204.8 cm³; (10)Polarizability: 28.87×10^-24 cm³; (11)Surface Tension: 54.4 dyne/cm; (12)Density: 1.319 g/cm³; (13)Flash Point: 207.1 °C; (14)Enthalpy of Vaporization: 69.85 kJ/mol; (15)Boiling Point: 418.8 °C at 760 mmHg; (16)Vapour Pressure: 1.31E-07 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O3c1c(ccc(O)c1)[C@@H]4Oc2cc(OC)ccc2[C@@H]4C3
(2) 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-/m0/s1
(3) InChIKey: NSRJSISNDPOJOP-BBRMVZONBK