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Name |
Chelidonine |
EINECS | 207-504-1 |
CAS No. | 476-32-4 | Density | 1.422 g/cm3 |
PSA | 60.39000 | LogP | 2.26920 |
Solubility | N/A | Melting Point |
135-140 °C |
Formula | C20H19NO5 | Boiling Point | 507.4 °C at 760 mmHg |
Molecular Weight | 353.375 | Flash Point | 260.7 °C |
Transport Information | UN 2811 | Appearance | N/A |
Safety | 20-45-36/37 | Risk Codes | 25-20/21/22 |
Molecular Structure | Hazard Symbols | Xn | |
Synonyms |
Chelidonine(6CI,7CI,8CI);[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol,5b,6,7,12b,13,14-hexahydro-13-methyl-, [5bR-(5ba,6b,12ba)]-;(+)-Chelidonine;Chelidonin;Stylophorine;[5bR-(5ba,6b,12ba)]-5b,6,7,12b,13,14-Hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol; |
Article Data | 4 |
C27H21NO7
chelidonine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In 1,4-dioxane at 20℃; for 19h; Reflux; Inert atmosphere; | 88% |
chelidonine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran; 1,4-dioxane for 17h; Reflux; | 82% |
(-)-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,10b,11,12-tetrahydrobenzo[c]phenanthridin-6(5H)-one
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 7 h / 85 °C / Inert atmosphere 2.1: dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere 3.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C 4.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere 4.2: 2 h / 0 °C / Inert atmosphere 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C 6.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere 7.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr 8.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere View Scheme |
(-)-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,10b-dihydrobenzo[c]phenanthridin-6(5H)-one
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere 2.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C 3.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere 3.2: 2 h / 0 °C / Inert atmosphere 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C 5.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere 6.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr 7.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere View Scheme |
(-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C 2.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere 2.2: 2 h / 0 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C 4.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere 5.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr 6.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere View Scheme |
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C 2: potassium hydroxide / 2 h / 0 - 20 °C 3: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 0 - 20 °C 4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C 5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere 6: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 7: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 8: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme |
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 0 - 20 °C 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C 3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere 4: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 5: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 6: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme |
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere 2: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 3: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 4: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme |
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 2: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 3: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme |
Chelidonine is an organic compound with the formula C20H19NO5, and its systematic name is the same with the product name. With the CAS registry number 476-32-4, it is also named as (5bR,6S,12bS)-13-Methyl-5b,6,7,12b,13,14-hexahydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol. It belongs to the product categories of Alkaloids. Its EINECS number is 207-504-1. In addition, the molecular weight is 353.37. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Natural Product.
Physical properties of Chelidonine are: (1)ACD/LogP: 2.899; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.91; (4)ACD/LogD (pH 7.4): 2.85; (5)ACD/BCF (pH 5.5): 9.53; (6)ACD/BCF (pH 7.4): 84.51; (7)ACD/KOC (pH 5.5): 91.21; (8)ACD/KOC (pH 7.4): 808.63; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 60.39 Å2; (13)Index of Refraction: 1.667; (14)Molar Refractivity: 92.483 cm3; (15)Molar Volume: 248.441 cm3; (16)Polarizability: 36.663×10-24cm3; (17)Surface Tension: 58.78 dyne/cm; (18)Density: 1.422 g/cm3; (19)Flash Point: 260.66 °C; (20)Enthalpy of Vaporization: 81.866 kJ/mol; (21)Boiling Point: 507.389 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
Uses of Chelidonine: it can be used to produce O-ethoxycarbonyl chelidonine at the temperature of 20 °C. It will need reagent pyridine and solvent CH2Cl2 with the reaction time of 5 hours. The yield is about 70.5%.
When you are using this chemical, please be cautious about it as the following:
This chemical is toxic if swallowed. It is harmful by inhalation, in contact with skin and if swallowed. When using it, you should not eat or drink. Moreover, you need to wear suitable protective clothing and gloves. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: O1c2c(OC1)c3c(cc2)[C@@H]5[C@H](N(C3)C)c4cc6OCOc6cc4C[C@@H]5O
(2)Std. InChI: InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1
(3)Std. InChIKey: GHKISGDRQRSCII-ZOCIIQOWSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LD50 | subcutaneous | 140mg/kg (140mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960. | |
dog | LD50 | subcutaneous | 500mg/kg (500mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960. | |
frog | LD50 | subcutaneous | 160mg/kg (160mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960. | |
mouse | LD50 | intravenous | 35mg/kg (35mg/kg) | Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 5, Pg. 163, 1946. | |
mouse | LD50 | subcutaneous | 125mg/kg (125mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960. | |
mouse | LD50 | unreported | 2750mg/kg (2750mg/kg) | Herba Polonica. Vol. 25, Pg. 209, 1979. | |
rabbit | LD50 | subcutaneous | 360mg/kg (360mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960. |