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CAS No.: | 476-70-0 |
---|---|
Name: | Boldine |
Molecular Structure: | |
Formula: | C19H21NO4 |
Molecular Weight: | 327.38 |
Synonyms: | 4H-Dibenzo[de,g]quinoline-2,9-diol,5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (S)-;6aa-Aporphine-2,9-diol,1,10-dimethoxy- (8CI);Boldine (6CI,7CI);(+)-(S)-Boldine;(+)-2,9-Dihydroxy-1,10-dimethoxyaporphine;(+)-Boldine;(S)-(+)-Boldine;(S)-Boldine;1,10-Dimethoxy-6aa-aporphine-2,9-diol; |
EINECS: | 207-509-9 |
Density: | 1.29 g/cm3 |
Melting Point: | 162-164 °C |
Boiling Point: | 529.3 °C at 760 mmHg |
Flash Point: | 273.9 °C |
Hazard Symbols: | Xn |
Risk Codes: | 22-36/37/38 |
Safety: | 1-20-24/25-45-36-26 |
PSA: | 62.16000 |
LogP: | 2.80500 |
Conditions | Yield |
---|---|
With water |
5-Chloro-1-phenyltetrazole
boldine
2,9-O,O-bis(1-phenyl-1H-tetrazol-5-yl)boldine
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 24h; Heating / reflux; | 96% |
With potassium carbonate; potassium iodide In acetonitrile at 90℃; for 24h; | 80% |
Conditions | Yield |
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With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 16h; | 87% |
Conditions | Yield |
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With potassium carbonate In ethanol at 70℃; for 9h; | 75% |
Conditions | Yield |
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In diethyl ether at 20℃; for 24h; | 65% |
Conditions | Yield |
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With bromine; acetic acid In chloroform at 20℃; Bromination; | A 64% B 9% |
With N-Bromosuccinimide; trifluoroacetic acid In chloroform at 20℃; for 1h; Bromination; | A 54% B 13% |
boldine
(S)-8-NO-boldine
Conditions | Yield |
---|---|
With sodium nitrite In acetic acid at 20℃; for 1h; | 64% |
trifluoroacetic acid
boldine
methyl iodide
A
N-methylsecoboldine trifluoroacetate
B
N,N-dimethylsecoboldine trifluoroacetate
C
N-methylboldine trifluoroacetate
Conditions | Yield |
---|---|
Stage #1: boldine; methyl iodide In methanol; acetonitrile at 20℃; for 6h; Stage #2: trifluoroacetic acid In methanol; water; acetonitrile for 1h; | A 7% B 3% C 51% |
Conditions | Yield |
---|---|
With N-chloro-succinimide; trifluoroacetic acid In chloroform at 22℃; for 1h; Chlorination; | A 48% B 19% |
boldine
Conditions | Yield |
---|---|
With N-iodo-succinimide; trifluoroacetic acid In chloroform at 20℃; for 2h; Iodination; | 47% |
Reported in EPA TSCA Inventory.
The systematic name of this chemical is 4H-Dibenzo[de,g]quinoline-2,9-diol,5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-. With the CAS registry number 476-70-0 and EINECS registry number 207-509-9, it is also named as (S)-boldine. In addition, the molecular formula is C19H21NO4 and the molecular weight is 327.37. It is an alkaloid that can be found in the boldo tre and in Lindera aggregata. Moreover, it belongs to the classes of Anti-Inflammatory Agents; Antioxidants; Drug / Therapeutic Agent; Neuromuscular Blocking Agents; Peripheral Nervous System Agents; Protective Agents; Natural Product.
Physical properties about 4H-Dibenzo[de,g]quinoline-2,9-diol,5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)- are: (1)ACD/LogP: 2.32; (2)#H bond acceptors: 5; (3)#H bond donors: 2; (4)#Freely Rotating Bonds: 4; (5)Polar Surface Area: 40.16 Å2; (6)Index of Refraction: 1.638; (7)Molar Refractivity: 91.22 cm3; (8)Molar Volume: 253.6 cm3; (9)Polarizability: 36.16 ×10-24cm3; (10)Surface Tension: 53.3 dyne/cm; (11)Density: 1.29 g/cm3; (12)Flash Point: 273.9 °C; (13)Enthalpy of Vaporization: 83.46 kJ/mol; (14)Boiling Point: 529.3 °C at 760 mmHg; (15)Vapour Pressure: 8.02E-12 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing and avoid contact with skin and eyes. And you can not eat or drink. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). Moreover, you should keep it locked up when store it.
You can still convert the following datas into molecular structure:
(1)SMILES: O(c1cc2c(cc1O)CC4c3c(cc(O)c(OC)c23)CCN4C)C
(2)InChI: InChI=1/C19H21NO4/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3
(3)InChIKey: LZJRNLRASBVRRX-UHFFFAOYAJ
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 145mg/kg (145mg/kg) | United States Patent Document. Vol. #4185119, | |
mouse | LD50 | intravenous | 90mg/kg (90mg/kg) | CARDIAC: CHANGE IN RATE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Annales Pharmaceutiques Francaises. Vol. 38, Pg. 537, 1980. |
mouse | LD50 | oral | 450mg/kg (450mg/kg) | CARDIAC: CHANGE IN RATE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Annales Pharmaceutiques Francaises. Vol. 38, Pg. 537, 1980. |