Boldine supplier | CasNO.476-70-0

Name
Boldine
EINECS 207-509-9
CAS No. 476-70-0
Density 1.29 g/cm³
Solubility
Melting Point 162-164 °C
Formula C₁₉H₂₁NO₄
Boiling Point 529.3 °C at 760 mmHg
Molecular Weight 327.38
Flash Point 273.9 °C
Transport Information
Appearance
Safety 1-20-24/25-45-36-26
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn
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;
PSA 62.16000
LogP 2.80500

Synthetic route

: 50-00-0
formaldehyd

: 64-18-6
formic acid

(+)-laurolitsine: (+)-laurolitsine

: 476-70-0
boldine

Conditions

Conditions	Yield
With water

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With potassium carbonate In ethanol at 70℃; for 9h;	75%

: 186581-53-3, 908094-01-9
diazomethane

: 476-70-0
boldine

: 20051-87-0, 517-65-7
(+)-Predicentrine

Conditions

Conditions	Yield
In diethyl ether at 20℃; for 24h;	65%

: 476-70-0
boldine

A: 63955-80-6
3,8-Dibromoboldine

B: 3-bromoboldine

Conditions

Conditions	Yield
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

Conditions	Yield
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

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%

...Expand

: 476-70-0
boldine

A: 3-chloroboldine

B: (S)-3,8-Dichloroboldine

Conditions

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

: 476-70-0
boldine

: 3-iodoboldine

Conditions

Conditions	Yield
With N-iodo-succinimide; trifluoroacetic acid In chloroform at 20℃; for 2h; Iodination;	47%

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 138-24-9
phenyltrimethylammonium chloride

: 476-70-0
boldine

A: (S)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-9-yl-trifluoro-methanesulfonate

B: predicentrine triflate

Conditions

Conditions	Yield
Stage #1: phenyltrimethylammonium chloride; boldine With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 12h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide With TEA; potassium carbonate In dichloromethane for 72h; Further stages.;	A 36% B 38%

...Expand

: 476-70-0
boldine

: 3-Bromoboldine

Conditions

Conditions	Yield
With N-Bromosuccinimide In trifluoroacetic acid at 20℃; for 3h;	35.9%

: 67-56-1
methanol

: 476-70-0
boldine

A: 20051-87-0, 517-65-7
(+)-Predicentrine

B: 2169-44-0
N-methyllaurotetanine

C: 475-81-0
glaucine

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	A n/a B n/a C 26%

...Expand

: 476-70-0
boldine

: 104385-34-4
(S)-1,10-Dimethoxy-6-methyl-6-oxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 2h; Heating;	20%

: 476-70-0
boldine

: (+)-<3,8-3H2>boldine

Conditions

Conditions	Yield
With tritium oxide; potassium tert-butylate at 100℃; for 110h; sealed tube;

: 3282-30-2
pivaloyl chloride

: 476-70-0
boldine

: 2,9-O,O'-dipivaloylboldine

: 186581-53-3, 908094-01-9
diazomethane

: 476-70-0
boldine

A: 20051-87-0, 517-65-7
(+)-Predicentrine

B: 475-81-0
glaucine

Conditions

Conditions	Yield
In methanol; diethyl ether

...Expand

: 98-04-4
phenyltrimethylammonium iodide

: 476-70-0
boldine

A: 20051-87-0, 517-65-7
(+)-Predicentrine

B: 475-81-0
glaucine

...Expand

: 106-95-6
allyl bromide

: 476-70-0
boldine

: N-allylsecoboldine

Conditions

Conditions	Yield
Heating;
In N,N-dimethyl-formamide at 100 - 110℃; for 2h;
In N,N-dimethyl-formamide at 100 - 110℃; for 2h;

: 138-24-9
phenyltrimethylammonium chloride

: 476-70-0
boldine

A: 20051-87-0, 517-65-7
(+)-Predicentrine

B: 2169-44-0
N-methyllaurotetanine

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 12h; Title compound not separated from byproducts.;

...Expand

: 476-70-0
boldine

: acetic acid 7-acetoxy-1-[2-(allyl-methyl-amino)-ethyl]-4,6-dimethoxy-phenanthren-3-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Heating 2: pyridine View Scheme

: 476-70-0
boldine

: 3-chloro-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; diethyl ether 2: 24 percent / N-chlorosuccinimide; trifluoroacetic acid / 2 h / 20 °C View Scheme

: 476-70-0
boldine

: 3-iodo-1,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; diethyl ether 2: 49 percent / N-iodosuccinimide; trifluoroacetic acid / 2 h / 20 °C View Scheme

: 476-70-0
boldine

: 3-iodo-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; diethyl ether 2: 26 percent / N-iodosuccinimide; trifluoroacetic acid / 2 h / 20 °C View Scheme

: 476-70-0
boldine

: (S)-3,8-Dichloroglaucine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; diethyl ether 2: 27 percent / N-chlorosuccinimide; trifluoroacetic acid / 2 h / 20 °C View Scheme

: 476-70-0
boldine

: 3,8-dibromo-1,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; diethyl ether 2: 24 percent / N-bromosuccinimide; trifluoroacetic acid / 2 h / 20 °C View Scheme

: 476-70-0
boldine

: 87167-04-2
3-bromopredicentrine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; diethyl ether 2: 55 percent / N-bromosuccinimide; trifluoroacetic acid / 2 h / 20 °C View Scheme

: 476-70-0
boldine

: 121387-31-3
3,8-dibromoglaucine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; diethyl ether 2: 47 percent / N-bromosuccinimide; trifluoroacetic acid / 2 h / 20 °C View Scheme

Boldine Consensus Reports

Reported in EPA TSCA Inventory.

Boldine 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.

Product Name

Boldine

Synthetic route

Boldine Consensus Reports

Boldine Specification

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