CAS No.476-32-4,CHELIDONINE Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	476-32-4
Name:	CHELIDONINE
Article Data:	4

Formula:	C₂₀H₁₉NO₅
Molecular Weight:	353.375
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;
EINECS:	207-504-1
Density:	1.422 g/cm³
Melting Point:	135-140 °C
Boiling Point:	507.4 °C at 760 mmHg
Flash Point:	260.7 °C
Hazard Symbols:	Xn
Risk Codes:	25-20/21/22
Safety:	20-45-36/37
Transport Information:	UN 2811
PSA:	60.39000
LogP:	2.26920

Synthetic route

: 1032645-05-8
C27H21NO7

: 476-32-4
chelidonine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In 1,4-dioxane at 20℃; for 19h; Reflux; Inert atmosphere;	88%

: methyl (5bR,5cR,6aS,11bS)-5b,6a,11b,13-tetrahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]oxireno[2,3-a]phenanthridine-12(5cH)-carboxylate

: 476-32-4
chelidonine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; 1,4-dioxane for 17h; Reflux;	82%

: 64-17-5
ethanol

: 24181-71-3
(+)-Didehydrochelidonin

NaBH4: NaBH4

: 476-32-4
chelidonine

...Expand

: 1337985-26-8
(-)-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,10b,11,12-tetrahydrobenzo[c]phenanthridin-6(5H)-one

: 476-32-4
chelidonine

Conditions

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

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

: 1337985-30-4
(-)-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,10b-dihydrobenzo[c]phenanthridin-6(5H)-one

: 476-32-4
chelidonine

Conditions

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

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

: 1337985-33-7
(-)-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

: 476-32-4
chelidonine

Conditions

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

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

: C22H19NO6

: 476-32-4
chelidonine

Conditions

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

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

: methyl ((1S,2R)-2-(4-(hydroxymethyl)benzo[d][1,3]dioxol-5-yl)-1-(6-vinylbenzo[d][1,3]dioxol-5-yl)but-3-en-1-yl)carbamate

: 476-32-4
chelidonine

Conditions

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

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

: methyl (6R,7S)-6-vinyl-7-(6-vinylbenzo[d][1,3]dioxol-5-yl)-6,9-dihydro-[1,3]dioxolo[4,5-h]isoquinoline-8(7H)-carboxylate

: 476-32-4
chelidonine

Conditions

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

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

: methyl (5bR,12bS)-5b,14-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridine-13(12bH)-carboxylate

: 476-32-4
chelidonine

Conditions

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

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Specification

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%.

Chelidonine can be used to produce O-ethoxycarbonyl chelidonine at the temperature of 20 °C

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)	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.