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Matrine

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Name

Matrine

EINECS 209-012-2
CAS No. 519-02-8 Density 1.16 g/cm3
PSA 23.55000 LogP 1.74750
Solubility Melting Point 77 °C
Formula C15H24N2O Boiling Point 396.7 °C at 760 mmHg
Molecular Weight 248.37 Flash Point 172.7 °C
Transport Information Appearance
Safety 22-26-36/37/39-45 Risk Codes 20/21/22-37/38-41-48
Molecular Structure Molecular Structure of 519-02-8 (1H,5H,10H-Dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one, dodecahydro-, (7aS,13aR,13bR,13cS)-) Hazard Symbols HarmfulXn
Synonyms

Matridin-15-one;Matridin-15-one (9CI);1H,5H,10H-Dipyrido[2,1-f:3',2',1'-ij][1,6]- naphthyridin-10-one,dodecahydro-,(7aS,- 13aR,13bR,13cS)-;Matrene, (+)-;5-24-02-00301 (Beilstein Handbook Reference);(+)-Matrine;Shrubby Sophora Extract;α-Matrine;Vegard;

 

Matrine Synthetic route

Conditions
ConditionsYield
With ammonium sulfate; tin(ll) chloride In water at 50℃; for 4h; Reagent/catalyst; Solvent; Temperature;96.9%
With tris(pentafluorophenyl)borate; phenylsilane In dichloromethane at 60℃; for 8h; Inert atmosphere; Schlenk technique; Green chemistry;82%

(6aS,11aR,11cS)-4,8-Dioxo-decahydro-3a,7a-diaza-benzo[de]anthracene-9,9-dicarboxylic acid dimethyl ester

519-02-8

(+)-matrine

Conditions
ConditionsYield
With hydrogenchloride; dimethylsulfide borane complex; water 2.) reflux; Yield given; Multistep reaction;
(-)-sophocarpine

(-)-sophocarpine

519-02-8

(+)-matrine

Conditions
ConditionsYield
With nickel Hydrogenation;
(-)-sophoramine

(-)-sophoramine

519-02-8

(+)-matrine

Conditions
ConditionsYield
With nickel Hydrogenation;
oxymatrine

oxymatrine

519-02-8

(+)-matrine

Conditions
ConditionsYield
With sulfur dioxide
65321-36-0

t-butyl nicotinate

519-02-8

(+)-matrine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 90 percent / H2 / Pd/C
2: Et3N
3: acetone
4: 18 percent / lauroyl peroxide / benzene / Heating
5: lauroyl peroxide, 2-propanol / Heating
6: 90 percent / CF3COOH / CH2Cl2
8: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme
4695-77-6

1,4,5,6-tetrahydro-pyridine-3-carboxylic acid tert-butyl ester

519-02-8

(+)-matrine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: Et3N
2: acetone
3: 18 percent / lauroyl peroxide / benzene / Heating
4: lauroyl peroxide, 2-propanol / Heating
5: 90 percent / CF3COOH / CH2Cl2
7: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme
208714-36-7

1-allyl-2-oxo-1,4-dihydro-2H-pyridine-3,3-dicarboxylic acid dimethyl ester

519-02-8

(+)-matrine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 30 percent / lauroyl peroxide / benzene / Heating
2: lauroyl peroxide, 2-propanol / Heating
3: 90 percent / CF3COOH / CH2Cl2
5: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme
Multi-step reaction with 6 steps
1: 30 percent / lauroyl peroxide / benzene / Heating
2: 80 percent / lauroyl peroxide / benzene
3: lauroyl peroxide, 2-propanol / Heating
4: 90 percent / CF3COOH / CH2Cl2
6: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme
Multi-step reaction with 5 steps
1: 18 percent / lauroyl peroxide / benzene / Heating
2: lauroyl peroxide, 2-propanol / Heating
3: 90 percent / CF3COOH / CH2Cl2
5: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme

1-chloroacetyl-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid tert-butyl ester

519-02-8

(+)-matrine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: acetone
2: 18 percent / lauroyl peroxide / benzene / Heating
3: lauroyl peroxide, 2-propanol / Heating
4: 90 percent / CF3COOH / CH2Cl2
6: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme

2-allylcarbamoyl-2-(3-oxo-propyl)-malonic acid dimethyl ester

519-02-8

(+)-matrine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: B(OH)3 / toluene / Heating
2: 30 percent / lauroyl peroxide / benzene / Heating
3: lauroyl peroxide, 2-propanol / Heating
4: 90 percent / CF3COOH / CH2Cl2
6: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme
Multi-step reaction with 7 steps
1: B(OH)3 / toluene / Heating
2: 30 percent / lauroyl peroxide / benzene / Heating
3: 80 percent / lauroyl peroxide / benzene
4: lauroyl peroxide, 2-propanol / Heating
5: 90 percent / CF3COOH / CH2Cl2
7: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme
Multi-step reaction with 6 steps
1: B(OH)3 / toluene / Heating
2: 18 percent / lauroyl peroxide / benzene / Heating
3: lauroyl peroxide, 2-propanol / Heating
4: 90 percent / CF3COOH / CH2Cl2
6: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme
208714-37-8

1-ethoxythiocarbonylsulfanylacetyl-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid tert-butyl ester

519-02-8

(+)-matrine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 18 percent / lauroyl peroxide / benzene / Heating
2: lauroyl peroxide, 2-propanol / Heating
3: 90 percent / CF3COOH / CH2Cl2
5: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme

(6aS,11aR,11bS,11cS)-4,8-Dioxo-octahydro-3a,7a-diaza-benzo[de]anthracene-9,9,11b-tricarboxylic acid dimethyl ester

519-02-8

(+)-matrine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme

(6aS,11aR,11bS,11cS)-4,8-Dioxo-octahydro-3a,7a-diaza-benzo[de]anthracene-9,9,11b-tricarboxylic acid 11b-tert-butyl ester 9,9-dimethyl ester

519-02-8

(+)-matrine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / CF3COOH / CH2Cl2
3: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme
208714-38-9

1-[5-(5-tert-butoxycarbonyl-3,4-dihydro-2H-pyridin-1-yl)-2-ethoxythiocarbonylsulfanyl-5-oxo-pentyl]-2-oxo-1,4-dihydro-2H-pyridine-3,3-dicarboxylic acid dimethyl ester

519-02-8

(+)-matrine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lauroyl peroxide, 2-propanol / Heating
2: 90 percent / CF3COOH / CH2Cl2
4: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme
Multi-step reaction with 5 steps
1: 80 percent / lauroyl peroxide / benzene
2: lauroyl peroxide, 2-propanol / Heating
3: 90 percent / CF3COOH / CH2Cl2
5: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme

11-ethoxythiocarbonylsulfanyl-4,8-dioxo-octahydro-3a,7a-diaza-benzo[de]anthracene-9,9,11b-tricarboxylic acid 11b-tert-butyl ester 9,9-dimethyl ester

519-02-8

(+)-matrine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lauroyl peroxide, 2-propanol / Heating
2: 90 percent / CF3COOH / CH2Cl2
4: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux
View Scheme
Conditions
ConditionsYield
With hydrogen; nickel In water at 20℃; for 8h;
16837-52-8

Oxymatrine

519-02-8

(+)-matrine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water at 80℃; for 48h; Reagent/catalyst; Solvent; Temperature;409.5 g
519-02-8

(+)-matrine

Conditions
ConditionsYield
With sodium hydroxide In water at 90℃; for 12h; Reagent/catalyst; Solvent;99%
With potassium hydroxide In water at 20℃; Reflux;98.3%
Stage #1: (+)-matrine With sodium hydroxide for 9h; Reflux;
Stage #2: With hydrogenchloride In water at 20℃;
98%
519-02-8

(+)-matrine

matrinic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 9h; Reflux;98.3%
616-38-6

carbonic acid dimethyl ester

519-02-8

(+)-matrine

4-methoxycarbonylmatrine

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 0℃; for 3h; Inert atmosphere;98%
With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere;97%
With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere;94%
Stage #1: (+)-matrine With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 1h;
Stage #2: carbonic acid dimethyl ester In tetrahydrofuran at -78 - 20℃; for 4.5h;
74%
67-56-1

methanol

519-02-8

(+)-matrine

109616-04-8

C16H28N2O2

Conditions
ConditionsYield
Stage #1: (+)-matrine With hydrogenchloride In water for 6h; Reflux;
Stage #2: methanol In water at 20℃; for 3h;
97%
Stage #1: (+)-matrine With sodium hydroxide for 9h; Reflux;
Stage #2: methanol With hydrogenchloride In water for 2h; Reflux;
76%
Stage #1: (+)-matrine With sodium hydroxide In water for 9h; Reflux;
Stage #2: methanol With hydrogenchloride In water for 2h; Reflux;
882-33-7

diphenyldisulfane

519-02-8

(+)-matrine

14-phenylthio matrine

Conditions
ConditionsYield
Stage #1: (+)-matrine With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane at -78 - 25℃; for 1.25h; Inert atmosphere; Green chemistry;
Stage #2: diphenyldisulfane In tetrahydrofuran; hexane Reagent/catalyst; Inert atmosphere; Green chemistry;
96%
Stage #1: (+)-matrine With lithium diisopropyl amide In tetrahydrofuran; hexane at 25℃; for 1h;
Stage #2: diphenyldisulfane In tetrahydrofuran; hexane at 25℃; for 2h;
96%
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 20℃; for 2h;96%
Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 10h; Reflux;95%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 10.1667h; Reflux;88%
With lithium aluminium tetrahydride In tetrahydrofuran Reflux;88%
With lithium aluminium tetrahydride In tetrahydrofuran for 10h; Reflux;
519-02-8

(+)-matrine

Conditions
ConditionsYield
With water; sodium hydroxide at 100℃; for 10h;95%
519-02-8

(+)-matrine

matrine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water for 3h;93%
68-12-2, 33513-42-7

N,N-dimethyl-formamide

519-02-8

(+)-matrine

14-formyl-15-chloromatrine

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In dichloromethane at 0℃; for 1h; Vilsmeier-Haack Formylation;
Stage #2: (+)-matrine In dichloromethane at 20℃; for 9h; Vilsmeier-Haack Formylation;
Stage #3: With sodium hydroxide In dichloromethane; water at 60℃; for 2h; pH=8 - 9; Vilsmeier-Haack Formylation;
92%
With trichlorophosphate In dichloromethane at 0 - 60℃; for 11h; Vilsmeier-Haack Formylation;92%
With trichlorophosphate In dichloromethane at 0 - 60℃; for 11h; Vilsmeier-Haack Formylation;92%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In dichloromethane at 0℃; for 1h;
Stage #2: (+)-matrine In dichloromethane at 0 - 20℃; for 8h;
85%
519-02-8

(+)-matrine

C15H25N3O

Conditions
ConditionsYield
With chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III); O-(2,4-dinitrophenyl)hydroxylamine In dichloromethane for 24h; Catalytic behavior; Reagent/catalyst; Solvent;89%
With manganese(III) 5,10,15,20-tetrakis-(2,6-dichlorophenyl) porphyrin; O-(2,4-dinitrophenyl)hydroxylamine In dichloromethane at 20℃; for 24h;89%
519-02-8

(+)-matrine

641-39-4

(+)-allomatrine

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In acetic acid for 15h; Heating;88%
With hydrogen; platinum(IV) oxide In water at 95 - 98℃; under 760 Torr; for 12h; Isomerization;452 mg
519-02-8

(+)-matrine

1345731-45-4

4-((1R,3aR,10aR,13aS)-decahydro-1H,4H-pyrido[3,2,1-ij][1,6]naphthyridin-1-yl)butyric acid

Conditions
ConditionsYield
With water; potassium hydroxide for 10h; Reflux;88%
519-02-8

(+)-matrine

(4S,7aS,13aR,13bR)-dodecahydro-1H,5H,8Hdipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridine-10-carbonitrile

Conditions
ConditionsYield
Stage #1: (+)-matrine With bis(triphenylphosphine)iridium(I) carbonyl chloride In toluene at 20℃; for 0.0833333h;
Stage #2: With 1,1,3,3-Tetramethyldisiloxane In toluene at 20℃; for 0.0833333h;
Stage #3: With trimethylsilyl cyanide In toluene at 20℃; for 0.5h;
85%
519-02-8

(+)-matrine

C15H22Cl2N2O

Conditions
ConditionsYield
With trichlorophosphate at 100℃; for 16h; Reagent/catalyst; Temperature;85%
941-55-9

4-toluenesulfonyl azide

519-02-8

(+)-matrine

C22H31N3O2S

Conditions
ConditionsYield
Stage #1: (+)-matrine With bis(triphenylphosphine)carbonyliridium(I) chloride; 1,1,3,3-Tetramethyldisiloxane In dichloromethane at 20℃; for 0.5h;
Stage #2: 4-toluenesulfonyl azide In dichloromethane at 20℃; for 3h; chemoselective reaction;
81%
67-56-1

methanol

519-02-8

(+)-matrine

matrinic acid methyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 115℃; for 24h;76%
67-56-1

methanol

519-02-8

(+)-matrine

methyl matrinate dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water for 24h; Reflux;76%
Stage #1: (+)-matrine With sodium hydroxide for 9h; Reflux;
Stage #2: With hydrogenchloride pH=5 - 6;
Stage #3: methanol With hydrogenchloride for 2h; Reflux;
62-53-3

aniline

519-02-8

(+)-matrine

(E)-15-(N-phenyl) matrinic imine

Conditions
ConditionsYield
Stage #1: (+)-matrine With trichlorophosphate In dichloromethane at 20 - 60℃;
Stage #2: aniline In dichloromethane at 60℃; for 12h;
73%

C21H36Cl2N5O5P

519-02-8

(+)-matrine

C30H49Cl2N8O3P

Conditions
ConditionsYield
Stage #1: C21H36Cl2N5O5P With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
Stage #2: (+)-matrine With trichlorophosphate In dichloromethane for 27h; Reflux;
71.2%
135-02-4

ortho-anisaldehyde

519-02-8

(+)-matrine

14-(2-methoxy)phenylmethylenematrine

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran for 12h; Reflux;67%
617-48-1

malic acid

519-02-8

(+)-matrine

matrine malate

Conditions
ConditionsYield
In ethanol for 3h;67%
519-02-8

(+)-matrine

14-oxime matrine

Conditions
ConditionsYield
Stage #1: (+)-matrine With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With tert.-butylnitrite In tetrahydrofuran at 20℃; for 2h;
67%
100-10-7

4-dimethylamino-benzaldehyde

519-02-8

(+)-matrine

14-(4-dimethylamino)phenylmethylenematrine

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran for 12h; Reflux;66%

copper(II) perchlorate hexahydrate

519-02-8

(+)-matrine

2ClO4(1-)*C30H54CuN4O5(2+)*2ClHO4

Conditions
ConditionsYield
In ethanol at 60℃; for 6h;61%
519-02-8

(+)-matrine

thiomatrine

Conditions
ConditionsYield
With Lawessons reagent In toluene at 100℃; for 6h;58%
With Lawessons reagent In toluene at 100℃; for 8h;50%
With Lawessons reagent
3770-50-1

2-carbethoxyindole

519-02-8

(+)-matrine

C24H29N3O2

Conditions
ConditionsYield
Stage #1: (+)-matrine With lithium diisopropyl amide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Cooling with ice;
Stage #2: 2-carbethoxyindole In tetrahydrofuran for 3h; Inert atmosphere;
53%
630-19-3

pivalaldehyde

519-02-8

(+)-matrine

14-tert-butylmethylenematrine

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran for 12h; Reflux;53%
519-02-8

(+)-matrine

1885-29-6

anthranilic acid nitrile

4-amino-quinolinomatrine

Conditions
ConditionsYield
Stage #1: (+)-matrine With trichlorophosphate In dichloromethane at 20 - 60℃;
Stage #2: anthranilic acid nitrile In dichloromethane at 60℃; for 12h;
53%
98-01-1

furfural

519-02-8

(+)-matrine

14-(2-furyl)methylenematrine

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran for 12h; Reflux;48%

Matrine Chemical Properties

Molecule structure of Matrine (CAS NO.519-02-8):

Molecular Formula: C15H24N2O
Molecular Weight: 248.363860 g/mol
Density: 1.16 g/cm3
Melting Point: 77 °C
Boiling Point: 396.7 °C at 760 mmHg 
Flash Point: 172.7 °C
Index of Refraction: 1.581
Molar Refractivity: 71.12 cm3
Molar Volume: 213.3 cm3 
Surface Tension: 48.3 dyne/cm 
Enthalpy of Vaporization: 64.71 kJ/mol
Vapour Pressure: 1.67E-06 mmHg at 25 °C 
XLogP3-AA: 1.6
H-Bond Acceptor: 2
Tautomer Count: 2
Exact Mass: 248.188863
MonoIsotopic Mass: 248.188863
Topological Polar Surface Area: 23.6
Heavy Atom Count: 18 
Canonical SMILES: C1CC2C3CCCN4C3C(CCC4)CN2C(=O)C1
InChI: InChI=1S/C15H24N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h11-13,15H,1-10H2
InChIKey: ZSBXGIUJOOQZMP-UHFFFAOYSA-N
EINECS: 209-012-2
Product Categories: Miscellaneous Natural Products; Natural Plant Extract

Matrine Uses

 Matrine (CAS NO.519-02-8) is an anti-inflammatory drug for the treatment of chronic cervicitis, dysentery, enteritis and other diseases antibacterial anti-inflammatory drugs for chronic cervicitis, dysentery, enteritis and so on.

Matrine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 74150ug/kg (74.15mg/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 201, 1992.
mouse LD50 intraperitoneal 150mg/kg (150mg/kg)   Zhongcaoyao. Chinese Traditional and Herbal Medicine. Vol. 18, Pg. 214, 1987.
mouse LD50 intravenous 64850ug/kg (64.85mg/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 201, 1992.
rat LD50 intraperitoneal 125mg/kg (125mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 18, Pg. 2555, 1970.
 

Matrine Safety Profile

Hazard Codes: Xn 
Risk Statements: 20/21/22-37/38-41-48
20/21/22: Harmful by inhalation, in contact with skin and if swallowed 
37/38: Irritating to respiratory system and skin
41: Risk of serious damage to eyes 
48: Danger of serious damage to health by prolonged exposure    
Safety Statements: 22-26-36/37/39-45
22: Do not breathe dust
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39: Wear suitable protective clothing, gloves and eye/face protection  
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)

Matrine Specification

 Matrine (CAS NO.519-02-8) is also named as (+)-Matrine ; 5-24-02-00301 (Beilstein Handbook Reference) ; BRN 0085851 ; Matrene, (+)- ; NSC 146051 ; Matridin-15-one (9CI) .

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