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476-70-0

Basic Information
CAS No.: 476-70-0
Name: Boldine
Molecular Structure:
Molecular Structure of 476-70-0 (Boldine)
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: HarmfulXn
Risk Codes: 22-36/37/38
Safety: 1-20-24/25-45-36-26
PSA: 62.16000
LogP: 2.80500
Synthetic route
50-00-0

formaldehyd

64-18-6

formic acid

(+)-laurolitsine

(+)-laurolitsine

476-70-0

boldine

Conditions
ConditionsYield
With water
14210-25-4

5-Chloro-1-phenyltetrazole

476-70-0

boldine

65979-75-1

2,9-O,O-bis(1-phenyl-1H-tetrazol-5-yl)boldine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 24h; Heating / reflux;96%
With potassium carbonate; potassium iodide In acetonitrile at 90℃; for 24h;80%
138-24-9

phenyltrimethylammonium chloride

476-70-0

boldine

475-81-0

glaucine

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 16h;87%
75-30-9

2-iodo-propane

476-70-0

boldine

2,9-diisopropyloxy-1,10-dimethoxy-N-methylaporphine

Conditions
ConditionsYield
With potassium carbonate In ethanol at 70℃; for 9h;75%
476-70-0

boldine

20051-87-0, 517-65-7

(+)-Predicentrine

Conditions
ConditionsYield
In diethyl ether at 20℃; for 24h;65%
476-70-0

boldine

A

63955-80-6

3,8-Dibromoboldine

B

3-bromoboldine

Conditions
ConditionsYield
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%
476-70-0

boldine

352670-72-5

(S)-8-NO-boldine

Conditions
ConditionsYield
With sodium nitrite In acetic acid at 20℃; for 1h;64%
76-05-1

trifluoroacetic acid

476-70-0

boldine

74-88-4

methyl iodide

A

1346153-51-2

N-methylsecoboldine trifluoroacetate

B

1346153-52-3

N,N-dimethylsecoboldine trifluoroacetate

C

1346153-50-1

N-methylboldine trifluoroacetate

Conditions
ConditionsYield
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%
476-70-0

boldine

A

3-chloroboldine

B

(S)-3,8-Dichloroboldine

Conditions
ConditionsYield
With N-chloro-succinimide; trifluoroacetic acid In chloroform at 22℃; for 1h; Chlorination;A 48%
B 19%
476-70-0

boldine

3-iodoboldine

Conditions
ConditionsYield
With N-iodo-succinimide; trifluoroacetic acid In chloroform at 20℃; for 2h; Iodination;47%
Raw Materials
50-00-0
64-18-6
Downstream Products
475-81-0
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  • Boldine  CAS NO.476-70-0

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

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.