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32383-76-9

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32383-76-9 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 32383-76-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,2,3,8 and 3 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 32383-76:
(7*3)+(6*2)+(5*3)+(4*8)+(3*3)+(2*7)+(1*6)=109
109 % 10 = 9
So 32383-76-9 is a valid CAS Registry Number.
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

32383-76-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (-)-medicarpin

1.2 Other means of identification

Product number -
Other names Demethylhomopterocarpin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:32383-76-9 SDS

32383-76-9Synthetic route

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

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

medicarpin
32383-76-9

medicarpin

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

2,7-dihydroxy-4'-methoxyisoflavanone

medicarpin
32383-76-9

medicarpin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2-hydroxyisoflavanone dehydratase
View Scheme
(2R,3S)-2,7,4'-trihydroxyisoflavanone
131887-80-4

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

medicarpin
32383-76-9

medicarpin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2-methoxyethanol / 2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase
2: 2-hydroxyisoflavanone dehydratase
View Scheme
3-(2,4-dimethoxyphenyl)-7-hydroxy-4H-chromen-4-one
1891-01-6

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

A

medicarpin
32383-76-9

medicarpin

B

medicarpin
33983-39-0

medicarpin

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

7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

A

medicarpin
32383-76-9

medicarpin

B

medicarpin
33983-39-0

medicarpin

Conditions
ConditionsYield
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
recorcinol
108-46-3

recorcinol

A

medicarpin
32383-76-9

medicarpin

B

medicarpin
33983-39-0

medicarpin

Conditions
ConditionsYield
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
9-methoxy-6a,11a-dihydro-6H-benzo[4,5]furo[3,2-c]chromen-3-ol
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

medicarpin
32383-76-9

medicarpin

B

medicarpin
33983-39-0

medicarpin

Conditions
ConditionsYield
With Lux cellulose-1 PHENOMENIX column In water; acetonitrile Resolution of racemate;A n/a
B n/a
2,4-dimethoxyphenylacetic acid
6496-89-5

2,4-dimethoxyphenylacetic acid

A

medicarpin
32383-76-9

medicarpin

B

medicarpin
33983-39-0

medicarpin

Conditions
ConditionsYield
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

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

medicarpin
32383-76-9

medicarpin

Conditions
ConditionsYield
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

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

medicarpin
32383-76-9

medicarpin

Conditions
ConditionsYield
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
(R)-7-(benzyloxy)-3-(2-(benzyloxy)-4-methoxyphenyl)chromane

(R)-7-(benzyloxy)-3-(2-(benzyloxy)-4-methoxyphenyl)chromane

medicarpin
32383-76-9

medicarpin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lead(II,IV) oxide / benzene / 3 h / 85 °C
2: palladium 10% on activated carbon; hydrogen / ethanol
3: potassium carbonate / ethyl acetate / 5 h / 20 °C
View Scheme
C32H30O6

C32H30O6

medicarpin
32383-76-9

medicarpin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / ethanol
2: potassium carbonate / ethyl acetate / 5 h / 20 °C
View Scheme
C18H18O6

C18H18O6

medicarpin
32383-76-9

medicarpin

Conditions
ConditionsYield
With potassium carbonate In ethyl acetate at 20℃; for 5h;112 mg
2-(benzyloxy)-4-methoxy-1-((E)-2-(((1R,2S)-2-phenylcyclohexyl)oxy)vinyl)benzene

2-(benzyloxy)-4-methoxy-1-((E)-2-(((1R,2S)-2-phenylcyclohexyl)oxy)vinyl)benzene

medicarpin
32383-76-9

medicarpin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethyl ether / 0.17 h / -78 °C
1.2: 20 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2.17 h / -78 °C
3.1: lead(II,IV) oxide / benzene / 3 h / 85 °C
4.1: palladium 10% on activated carbon; hydrogen / ethanol
5.1: potassium carbonate / ethyl acetate / 5 h / 20 °C
View Scheme
C19H22O5
1019848-76-0

C19H22O5

medicarpin
32383-76-9

medicarpin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethyl ether / 0.17 h / -78 °C
1.2: 20 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2.17 h / -78 °C
3.1: lead(II,IV) oxide / benzene / 3 h / 85 °C
4.1: palladium 10% on activated carbon; hydrogen / ethanol
5.1: potassium carbonate / ethyl acetate / 5 h / 20 °C
View Scheme
C20H27ClO2Si

C20H27ClO2Si

A

medicarpin
32383-76-9

medicarpin

B

medicarpin
33983-39-0

medicarpin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: (S)-2-(fluorodiphenylmethyl)pyrrolidine; 4-nitro-benzoic acid; tetrabutyl ammonium fluoride; sodium dihydrogenphosphate / dichloromethane; tetrahydrofuran / 16 h / -40 °C
2.1: sodium tetrahydroborate / methanol / 0 °C
3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C
4.1: lead(II,IV) oxide; acetic acid / benzene / 3 h / 85 °C
4.2: 20 °C
4.3: 20 °C
View Scheme
2-benzyloxyl-4-methoxyphenylacetaldehyde

2-benzyloxyl-4-methoxyphenylacetaldehyde

A

medicarpin
32383-76-9

medicarpin

B

medicarpin
33983-39-0

medicarpin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: (S)-2-(fluorodiphenylmethyl)pyrrolidine; 4-nitro-benzoic acid; tetrabutyl ammonium fluoride; sodium dihydrogenphosphate / dichloromethane; tetrahydrofuran / 16 h / -40 °C
2.1: sodium tetrahydroborate / methanol / 0 °C
3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C
4.1: lead(II,IV) oxide; acetic acid / benzene / 3 h / 85 °C
4.2: 20 °C
4.3: 20 °C
View Scheme
(S)-5-(benzyloxy)-2-(2-(2-(benzyloxy)-4-methoxyphenyl)-3-hydroxypropyl)phenol

(S)-5-(benzyloxy)-2-(2-(2-(benzyloxy)-4-methoxyphenyl)-3-hydroxypropyl)phenol

A

medicarpin
32383-76-9

medicarpin

B

medicarpin
33983-39-0

medicarpin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C
2.1: lead(II,IV) oxide; acetic acid / benzene / 3 h / 85 °C
2.2: 20 °C
2.3: 20 °C
View Scheme
C30H28O5

C30H28O5

A

medicarpin
32383-76-9

medicarpin

B

medicarpin
33983-39-0

medicarpin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate / methanol / 0 °C
2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C
3.1: lead(II,IV) oxide; acetic acid / benzene / 3 h / 85 °C
3.2: 20 °C
3.3: 20 °C
View Scheme
C30H28O4

C30H28O4

A

medicarpin
32383-76-9

medicarpin

B

medicarpin
33983-39-0

medicarpin

Conditions
ConditionsYield
Stage #1: C30H28O4 With lead(II,IV) oxide; acetic acid In benzene at 85℃; for 3h;
Stage #2: With 10 wt% Pd(OH)2 on carbon; hydrogen In tetrahydrofuran; ethanol at 20℃;
Stage #3: With potassium carbonate In ethyl acetate at 20℃; Overall yield = 49 %; Overall yield = 13 mg; enantioselective reaction;
A n/a
B n/a
medicarpin
32383-76-9

medicarpin

dimethylallyl diphosphate
358-72-5

dimethylallyl diphosphate

licoagrocarpin

licoagrocarpin

Conditions
ConditionsYield
With maackiain-4-dimethylallyltransferase from Psoralea corylifolia; magnesium chloride In aq. buffer at 30℃; for 1h; pH=9; Enzymatic reaction; regioselective reaction;
medicarpin
32383-76-9

medicarpin

uridine-5'-diphosphoglucose
952585-00-1

uridine-5'-diphosphoglucose

medicarpin 3‐O‐β‐D‐glucoside

medicarpin 3‐O‐β‐D‐glucoside

Conditions
ConditionsYield
With TcCGT1-C-glycosyltransferase from Trolliuschinensisuridine in complex with uridine diphosphate In aq. phosphate buffer at 30℃; for 2h; pH=8; Enzymatic reaction;
medicarpin
32383-76-9

medicarpin

dimethylallyl diphosphate
358-72-5

dimethylallyl diphosphate

(-)-3-O-isoprenylmedicarpin

(-)-3-O-isoprenylmedicarpin

Conditions
ConditionsYield
With recombinant O-prenyltransferase from Antrodia camphorata In aq. buffer at 37℃; for 12h; pH=7; Enzymatic reaction;

32383-76-9Relevant articles and documents

Cornia,Merlini

, p. 428 (1975)

Unified total syntheses of (-)-medicarpin, (-)-sophoracarpan a, and (±)-kushecarpin a with some structural revisions

Feng, Zhen-Gao,Bai, Wen-Ju,Pettus, Thomas R. R.

, p. 1864 - 1867 (2015/02/19)

The total syntheses of medicarpin, sophoracarpan A, and kushecarpin A from a common intermediate are achieved by using ortho- and para-quinone methide chemistry. Additionally, the relative stereochemistry of sophoracarpan A and B have been reassigned.

Catalytic specificity of pea O-methyltransferases suggests gene duplication for (+)-pisatin biosynthesis

Akashi, Tomoyoshi,VanEtten, Hans D.,Sawada, Yuji,Wasmann, Catherine C.,Uchiyama, Hiroshi,Ayabe, Shin-ichi

, p. 2525 - 2530 (2007/10/03)

S-adenosyl-l-methionine: 2-hydroxyisoflavanone 4′-O-methyltransferase (HI4′OMT) methylates 2,7, 4′-trihydroxyisoflavanone to produce formononetin, an essential intermediate in the synthesis of isoflavonoids with methoxy or methylenedioxy groups at carbon 4′ (isoflavone numbering). HI4′OMT is highly similar (83% amino acid identity) to (+)-6a-hydroxymaackiain 3-O-methyltransferase (HMM), which catalyzes the last step of (+)-pisatin biosynthesis in pea. Pea contains two linked copies of HMM with 96% amino acid identity. In this report, the catalytic activities of the licorice HI4′OMT protein and of extracts of Escherichia coli containing the pea HMM1 or HMM2 protein are compared on 2,7,4′-trihydroxyisoflavanone and enantiomers of 6a-hydroxymaackiain. All these enzymes produced radiolabelled 2,7-dihydroxy-4′-methoxyisoflavanone or (+)-pisatin from 2,7,4′-trihydroxyisoflavanone or (+)-6a-hydroxymaakiain when incubated with [methyl-14C]-S-adenosyl-l-methionine. No product was detected when (-)-6a-hydroxymaackiain was used as the substrate. HI4′OMT and HMM1 showed efficiencies (relative Vmax/Km) for the methylation of 2,7,4′-trihydroxyisoflavanone 20 and 4 times higher than for the methylation of (+)-6a-hydroxymaackiain, respectively. In contrast, HMM2 had a higher Vmax and lower Km on (+)-6a-hydroxymaackiain, and had a 67-fold higher efficiency for the methylation of (+)-6a-hydroxymaackiain than that for 2,7,4′-trihydroxyisoflavanone. Among the 15 sites at which HMM1 and HMM2 have different amino acid residues, 11 of the residues in HMM1 are the same as found in HI4′OMTs from three plant species. Modeling of the HMM proteins identified three or four putative active site residues responsible for their different substrate preferences. It is proposed that HMM1 is the pea HI4′OMT and that HMM2 evolved by the duplication of a gene encoding a general biosynthetic enzyme (HI4′OMT).

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