(+)-matrine
Conditions | Yield |
---|---|
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% |
(+)-matrine
Conditions | Yield |
---|---|
With hydrogenchloride; dimethylsulfide borane complex; water 2.) reflux; Yield given; Multistep reaction; |
(+)-matrine
Conditions | Yield |
---|---|
With nickel Hydrogenation; |
(+)-matrine
Conditions | Yield |
---|---|
With nickel Hydrogenation; |
(+)-matrine
Conditions | Yield |
---|---|
With sulfur dioxide |
t-butyl nicotinate
(+)-matrine
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
1-allyl-2-oxo-1,4-dihydro-2H-pyridine-3,3-dicarboxylic acid dimethyl ester
(+)-matrine
Conditions | Yield |
---|---|
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 |
(+)-matrine
Conditions | Yield |
---|---|
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 |
(+)-matrine
Conditions | Yield |
---|---|
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 |
1-ethoxythiocarbonylsulfanylacetyl-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid tert-butyl ester
(+)-matrine
Conditions | Yield |
---|---|
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 |
(+)-matrine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux View Scheme |
(+)-matrine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / CF3COOH / CH2Cl2 3: 1.) BH3*Me2S, 2.) HCl, H2O / 2.) reflux View Scheme |
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
(+)-matrine
Conditions | Yield |
---|---|
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 |
(+)-matrine
Conditions | Yield |
---|---|
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 |
(+)-sophocarpine N-oxide
(+)-matrine
Conditions | Yield |
---|---|
With hydrogen; nickel In water at 20℃; for 8h; |
Oxymatrine
(+)-matrine
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol; water at 80℃; for 48h; Reagent/catalyst; Solvent; Temperature; | 409.5 g |
(+)-matrine
matrinic acid
Conditions | Yield |
---|---|
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% |
(+)-matrine
Conditions | Yield |
---|---|
With potassium hydroxide In water at 20℃; for 9h; Reflux; | 98.3% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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% |
(+)-matrine
Conditions | Yield |
---|---|
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; |
(+)-matrine
matrinic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide at 100℃; for 10h; | 95% |
(+)-matrine
Conditions | Yield |
---|---|
With hydrogenchloride In water for 3h; | 93% |
Conditions | Yield |
---|---|
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% |
(+)-matrine
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 |
(+)-matrine
4-((1R,3aR,10aR,13aS)-decahydro-1H,4H-pyrido[3,2,1-ij][1,6]naphthyridin-1-yl)butyric acid
Conditions | Yield |
---|---|
With water; potassium hydroxide for 10h; Reflux; | 88% |
(+)-matrine
Conditions | Yield |
---|---|
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% |
(+)-matrine
Conditions | Yield |
---|---|
With trichlorophosphate at 100℃; for 16h; Reagent/catalyst; Temperature; | 85% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With hydrogenchloride In water at 115℃; for 24h; | 76% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
Stage #1: (+)-matrine With trichlorophosphate In dichloromethane at 20 - 60℃; Stage #2: aniline In dichloromethane at 60℃; for 12h; | 73% |
Conditions | Yield |
---|---|
Stage #1: C21H36Cl2N5O5P With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: (+)-matrine With trichlorophosphate In dichloromethane for 27h; Reflux; | 71.2% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran for 12h; Reflux; | 67% |
Conditions | Yield |
---|---|
In ethanol for 3h; | 67% |
(+)-matrine
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran for 12h; Reflux; | 66% |
Conditions | Yield |
---|---|
In ethanol at 60℃; for 6h; | 61% |
(+)-matrine
Conditions | Yield |
---|---|
With Lawessons reagent In toluene at 100℃; for 6h; | 58% |
With Lawessons reagent In toluene at 100℃; for 8h; | 50% |
With Lawessons reagent |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran for 12h; Reflux; | 53% |
Conditions | Yield |
---|---|
Stage #1: (+)-matrine With trichlorophosphate In dichloromethane at 20 - 60℃; Stage #2: anthranilic acid nitrile In dichloromethane at 60℃; for 12h; | 53% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran for 12h; Reflux; | 48% |
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 (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.
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. |
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 (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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