(+)-Boldine
Basic information
- CAS
476-70-0- Standard SMILES
COc1cc2c(cc1O)C[C@H]1c3c(cc(O)c(OC)c3-2)CCN1C- InChIKey
LZJRNLRASBVRRX-ZDUSSCGKSA-N- Molecular formula
- C19H21NO4
- Average molar mass
- 327.4 g/mol
- Monoisotopic mass
- 327.14705815
Overview
Boldine is an aporphine alkaloid.
Names & identifiers
- Preferred name
- (+)-Boldine
- IUPAC
- (6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
- English name
- Boldine
- Molecular formula
- C19H21NO4
- Molecular weight
- 327.37
Names & synonyms
Boldine476-70-0(S)-Boldine(+)-Boldine1,10-Dimethoxy-2,9-dihydroxyaporphineDTXSID408833948I91GE27694H-Dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-4H-Dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-NSC-65689RefChem:30175DTXCID801022928
Show more names
(s)-ylBOLDINE(RG)(+)-(s)-boldine
207-509-9UniboldinaBoldinBoldine chloroformBoldine (Standard)ex Peumus boldusBoldine CRSAprophine alkaloid
Database identifiers
- CAS
476-70-0- PubChem CID
- 10154
- DTXSID
DTXSID40883394- ChEMBL
CHEMBL388342- ChEBI
CHEBI:3148- UNII
- 8I91GE2769
- EC Number
- 207-509-9
- Nikkaji
- J312.540H
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 62.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 461
Experimental & physicochemical properties
Collision Cross Section
177.08 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
179.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 162 · 162-164 °C
- Boiling point
- 465.27 °C · 465.27°C (rough estimate)
- Density
- 1.2223 · 1.2223 (rough estimate)
- refractive index
- 1.5 · 1.5000 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Acetonitrile (Slightly), Ethyl Acetate (Slightly, Heated), Methanol (Slightly)
- form
- Solid
- pka
- 9.75 · 9.75±0.20(Predicted)
- color
- Yellow to Dark Brown
- Merck
- 13 · 13,1316
- BRN
- 94036 · 94036
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- CE0750000
- ridadr
- 1544
- hs_code
- 29399990
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 1-20-24/25-45-36-26
- hazard_class
- 6.1(b)
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Drugs that interrupt transmission at the skeletal neuromuscular junction by causing sustained depolarization of the motor end plate. These agents are primarily used as adjuvants in surgical anesthesia to cause skeletal muscle relaxation.
Uses & manufacturing
General Manufacturing Information4H-Dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-: INACTIVE
Applications
Usesantineoplastic
Usesboldine is attributed with strong anti-oxidant properties. It has also demonstrated an ability to protect against uVB rays. Boldine is a constituent of the boldo plant (Peumus boldus Mol.) native to Chile, and is found in the plant’s leaves and bark.
Additional notes
DefinitionChEBI: Boldine is an aporphine alkaloid.
Related reactions
2 records
Compound notes
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