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519-02-8

Basic Information
CAS No.: 519-02-8
Name: Matrine
Article Data: 5
Molecular Structure:
Molecular Structure of 519-02-8 (Matrine)
Formula: C15H24N2O
Molecular Weight: 248.368
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;
EINECS: 209-012-2
Density: 1.16 g/cm3
Melting Point: 77 °C
Boiling Point: 396.7 °C at 760 mmHg
Flash Point: 172.7 °C
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-37/38-41-48
Safety: 22-26-36/37/39-45
PSA: 23.55000
LogP: 1.74750
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
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    Name: Matrine Synonyms: (5beta)-matridin-15-one CAS:519-02-8 MF: C15H24N2O Appearance:White powder Storage:Store in cool and dry place, away from sun light. Package:25kg/drum Application:APIs Transportation:By sea or by air Port:Qingdao Por

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Chemistry

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

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.

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.
 

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)

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) .