Boldine

Names

[ CAS No. ]:
476-70-0

[ Name ]:
Boldine

[Synonym ]:
Boldine chloroform
4H-Dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-
Boldin
2,6-dihydroxy-3,5-dimethoxyaporphine
5,6,6a,7-Tetrahydro-1,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,9-diol
EINECS 207-509-9
1,10-dimethoxy-2,9-dihydroxyaporphine
Uniboldina
MFCD00135040
2,9-Dihydroxy-1,10-dimethoxyaporphine
1,10-Dimethoxy-6aa-aporphine-2,9-diol
dl-Boldine
Boldine
1,10-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol

Biological Activity

[Description]:

Boldine is an aporphine isoquinoline alkaloid extracted from the root of Litsea cubeba and also possesses these properties, including antioxidant, anti-inflammatory and cytoprotective effects. Boldine suppresses osteoclastogenesis, improves bone destruction by down-regulating the OPG/RANKL/RANK signal pathway and may be a potential therapeutic agent for rheumatoid arthritis[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[Target]

OPG/RANKL/RANK[1]

[References]

[1]. Zhao H , et al. Boldine isolated from Litsea cubeba inhibits bone resorption by suppressing the osteoclast differentiation in collagen-induced arthritis. Int Immunopharmacol. 2017 Oct;51:114-123.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
529.3±50.0 °C at 760 mmHg

[ Melting Point ]:
162-164ºC

[ Molecular Formula ]:
C₁₉H₂₁NO₄

[ Molecular Weight ]:
327.374

[ Flash Point ]:
273.9±30.1 °C

[ Exact Mass ]:
327.147064

[ PSA ]:
62.16000

[ LogP ]:
2.32

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.639

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CE0750000

CHEMICAL NAME :: 6a-alpha-Aporphine-2,9-diol, 1,10-dimethoxy-

CAS REGISTRY NUMBER :: 476-70-0

BEILSTEIN REFERENCE NO. :: 0094036

LAST UPDATED :: 199703

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C19-H21-N-O4

MOLECULAR WEIGHT :: 327.41

WISWESSER LINE NOTATION :: T C6666 1A Q KN&TT&J EO1 FQ K1 PQ QO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 450 mg/kg

TOXIC EFFECTS :: Cardiac - change in rate Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 145 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 90 mg/kg

TOXIC EFFECTS :: Cardiac - change in rate Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - other changes

MUTATION DATA

TYPE OF TEST :: Gene conversion and mitotic recombination

TEST SYSTEM :: Yeast - Saccharomyces cerevisiae

DOSE/DURATION :: 100 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 260,145,1991

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
1-20-24/25-45-36-26

[ RIDADR ]:
UN 1544

[ WGK Germany ]:
3

[ RTECS ]:
CE0750000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Applied biological and physicochemical activity of isoquinoline alkaloids: oxoisoaporphine and boldine.

Molecules 17(9) , 10958-70, (2012)

The aim of this study was to determine the electronic influence of substituent groups and annelated rings such as oxazole-oxazinone on the physicochemical and photoprotection, antioxidant capacity, to...

Are extraction methods in quantitative assays of pharmacopoeia monographs exhaustive? A comparison with pressurized liquid extraction.

Planta Med. 72(12) , 1157-62, (2006)

The extraction methods in selected monographs of the European and the Swiss Pharmacopoeia were compared to pressurized liquid extraction (PLE) with respect to the yield of constituents to be dosed in ...

8-NH2-boldine, an antagonist of alpha1A and alpha1B adrenoceptors without affinity for the alpha1D subtype: structural requirements for aporphines at alpha1-adrenoceptor subtypes.

Planta Med. 71(10) , 897-903, (2005)

Structure-activity analysis of 21 aporphine derivatives was performed by examining their affinities for cloned human alpha (1A), alpha (1B) and alpha (1D) adrenoceptors (AR) using membranes prepared f...