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Chelidonine
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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 Molecular Structure of 476-32-4 (CHELIDONINE) Hazard Symbols HarmfulXn
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

Chelidonine Synthetic route

1032645-05-8

C27H21NO7

476-32-4

chelidonine

Conditions
ConditionsYield
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
ConditionsYield
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

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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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 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) 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.

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