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Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Melting Point: | 162.00 to 165.00 °C. @ 760.00 mm Hg
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| Boiling Point: | 529.35 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 525.00 °F. TCC ( 273.90 °C. ) (est)
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| logP (o/w): | 0.837 (est) |
| Soluble in: |
| | water, 56.14 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
intraperitoneal-mouse LD50 145 mg/kg United States Patent Document. Vol. #4185119
intravenous-mouse LD50 90 mg/kg LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
CARDIAC: CHANGE IN RATE
VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Annales Pharmaceutiques Francaises. Vol. 38, Pg. 537, 1980.
oral-mouse LD50 450 mg/kg VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
CARDIAC: CHANGE IN RATE Annales Pharmaceutiques Francaises. Vol. 38, Pg. 537, 1980.
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | natural substances and extractives |
| Recommendation for (+)-boldine usage levels up to: | | | not for fragrance use.
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| Recommendation for (+)-boldine flavor usage levels up to: |
| | not for flavor use.
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Safety References:
| EPI System: | View |
| Cancer Citations: | Search |
| Toxicology Citations: | Search |
| EPA Substance Registry Services (TSCA): | 476-70-0 |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 10154 |
| National Institute of Allergy and Infectious Diseases: | Data |
| WGK Germany: | 3 |
| | (6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol |
| Chemidplus: | 0000476700 |
| RTECS: | CE0750000 for cas# 476-70-0 |
References:
| | (6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 10154 |
| Pubchem (sid): | 134973663 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | aprophine alkaloid | | (S)- | boldine | | | boldine-chloroform | | 4H- | 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-, (S)- | | 4H- | 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-, (S)- | | (9S)-4,16- | dimethoxy-10-methyl-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol | | (6aS)-1,10- | dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol | | (S)-1,10- | dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol |
Articles:
| PubMed: | [Behavioural impairments and hallucinations after consumption of boldo leaf infusions]. |
| PubMed: | A novel UPLC-MS/MS method for sensitive quantitation of boldine in plasma, a potential anti-inflammatory agent: application to a pharmacokinetic study in rats. |
| PubMed: | Surface enhanced Raman scattering study of the antioxidant alkaloid boldine using prismatic silver nanoparticles. |
| PubMed: | Immunomodulatory effect of an isolated fraction from Tinospora crispa on intracellular expression of INF-γ, IL-6 and IL-8. |
| PubMed: | Natural products as potential human ether-a-go-go-related gene channel inhibitors - screening of plant-derived alkaloids. |
| PubMed: | Evaluation of cytotoxic and chemotherapeutic properties of boldine in breast cancer using in vitro and in vivo models. |
| PubMed: | Antiplasmodial and antioxidant isoquinoline alkaloids from Dehaasia longipedicellata. |
| PubMed: | Natural compounds boldine and menthol are antagonists of human 5-HT3 receptors: implications for treating gastrointestinal disorders. |
| PubMed: | Boldine and related aporphines: from antioxidant to antiproliferative properties. |
| PubMed: | Boldine prevents renal alterations in diabetic rats. |
| PubMed: | Boldine induces cell cycle arrest and apoptosis in T24 human bladder cancer cell line via regulation of ERK, AKT, and GSK-3β. |
| PubMed: | Boldine improves endothelial function in diabetic db/db mice through inhibition of angiotensin II-mediated BMP4-oxidative stress cascade. |
| PubMed: | Development of an HPLC fluorescence method for determination of boldine in plasma, bile and urine of rats and identification of its major metabolites by LC-MS/MS. |
| PubMed: | Batch and Continuous Ultrasound Assisted Extraction of Boldo Leaves (Peumus boldus Mol.). |
| PubMed: | Boldine protects endothelial function in hyperglycemia-induced oxidative stress through an antioxidant mechanism. |
| PubMed: | Applied biological and physicochemical activity of isoquinoline alkaloids: oxoisoaporphine and boldine. |
| PubMed: | Acetylcholinesterase inhibition, antioxidant activity and toxicity of Peumus boldus water extracts on HeLa and Caco-2 cell lines. |
| PubMed: | (-)-Kunstleramide, a new antioxidant and cytotoxic dienamide from the bark of Beilschmiedia kunstleri gamble. |
| PubMed: | The aporphine alkaloid boldine improves endothelial function in spontaneously hypertensive rats. |
| PubMed: | Anti-acetylcholinesterase, anti-α-glucosidase, anti-leishmanial and anti-fungal activities of chemical constituents of Beilschmiedia species. |
| PubMed: | Alkaloids from the Chinese vine Gnetum montanum. |
| PubMed: | Boldo prevents UV light and nitric oxide-mediated plasmid DNA damage and reduces the expression of Hsp70 protein in melanoma cancer cells. |
| PubMed: | (+)-Kunstlerone, a new antioxidant neolignan from the Leaves of Beilschmiedia kunstleri gamble. |
| PubMed: | Lancifoliaine, a new bisbenzylisoquinoline from the bark of Litsea lancifolia. |
| PubMed: | In vitro cytotoxic evaluation of a novel phosphinyl derivative of boldine. |
| PubMed: | New alkaloid antibiotics that target the DNA topoisomerase I of Streptococcus pneumoniae. |
| PubMed: | Cytotoxic thiocarbamate derivatives of boldine. |
| PubMed: | Quantitative analysis of boldine alkaloid in natural extracts by cyclic voltammetry at a liquid-liquid interface and validation of the method by comparison with high performance liquid chromatography. |
| PubMed: | Direct identification of phenolic constituents in Boldo Folium (Peumus boldus Mol.) infusions by high-performance liquid chromatography with diode array detection and electrospray ionization tandem mass spectrometry. |
| PubMed: | The aporphine alkaloid boldine induces adiponectin expression and regulation in 3T3-L1 cells. |
| PubMed: | (+)-N-(2-hydroxypropyl)lindcarpine: a new cytotoxic aporphine isolated from Actinodaphne pruinosa Nees. |
| PubMed: | [Simultaneous determination of four alkaloids in Lindera aggregate by high performance liquid chromatography]. |
| PubMed: | Alkaloids from Lindera aggregata. |
| PubMed: | Grandine A, a new proaporphine alkaloid from the bark of Phoebe grandis. |
| PubMed: | Effect of boldo (Peumus boldus Molina) infusion on lipoperoxidation induced by cisplatin in mice liver. |
| PubMed: | Boldine: a potential new antiproliferative drug against glioma cell lines. |
| PubMed: | Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography-tandem mass spectrometry. |
| PubMed: | 5-Hydroxytryptamine2A receptor binding activity of compounds from Litsea sessilis. |
| PubMed: | Antioxidant and pro-oxidant properties of boldine on hippocampal slices exposed to oxygen-glucose deprivation in vitro. |
| PubMed: | Aporphine metho salts as neuronal nicotinic acetylcholine receptor blockers. |
| PubMed: | Characterization of isoquinoline alkaloids from Neolitsea sericea var. aurata by HPLC-SPE-NMR. |
| PubMed: | Studies of Genetic Variation of Essential Oil and Alkaloid Content in Boldo (Peumus boldus). |
| PubMed: | Advances in development of dopaminergic aporphinoids. |
| PubMed: | Are extraction methods in quantitative assays of pharmacopoeia monographs exhaustive? A comparison with pressurized liquid extraction. |
| PubMed: | Antihyperglycemic effect of aporphines and their derivatives in normal and diabetic rats. |
| PubMed: | Sensitive quantification of apomorphine in human plasma using a LC-ESI-MS-MS method. |
| PubMed: | Antinociceptive and free radical scavenging activities of alkaloids isolated from Lindera angustifolia Chen. |
| PubMed: | [Alkaloids from the root of Lindera angustifolia]. |
| PubMed: | 8-NH2-boldine, an antagonist of alpha1A and alpha1B adrenoceptors without affinity for the alpha1D subtype: structural requirements for aporphines at alpha1-adrenoceptor subtypes. |
| PubMed: | Boldine and its antioxidant or health-promoting properties. |
| PubMed: | Photostability and photoprotection factor of boldine and glaucine. |
| PubMed: | Effect of boldine, secoboldine, and boldine methine on angiotensin II-induced neutrophil recruitment in vivo. |
| PubMed: | Structure-affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: halogenation and D1 receptor selectivity. |
| PubMed: | Cytotoxic and antitumor potentialities of aporphinoid alkaloids. |
| PubMed: | Photochemistry of phytoalexins containing phenalenone-like chromophores: photophysics and singlet oxygen photosensitizing properties of the plant oxoaporphine alkaloid oxoglaucine. |
| PubMed: | Reactive oxygen species (ROS) generation inhibited by aporphine and phenanthrene alkaloids semi-synthesized from natural boldine. |
| PubMed: | Alkaloids from Cassytha filiformis and related aporphines: antitrypanosomal activity, cytotoxicity, and interaction with DNA and topoisomerases. |
| PubMed: | A novel alkaloid antioxidant, Boldine and synthetic antioxidant, reduced form of RU486, inhibit the oxidation of LDL in-vitro and atherosclerosis in vivo in LDLR(-/-) mice. |
| PubMed: | Inhibitory action of conventional food-grade natural antioxidants and of natural antioxidants of new development on the thermal-induced oxidation of cholesterol. |
| PubMed: | Spectroscopic study of antileishmanial drug incubated in the promastigotes of Leishmania mexicana. |
| PubMed: | Sipaucins A-C, sesquiterpenoids from Siparuna pauciflora. |
| PubMed: | Free-radical scavengers and antioxidants from Peumus boldus Mol. ("Boldo"). |
| PubMed: | Effects of some antioxidative aporphine derivatives on striatal dopaminergic transmission and on MPTP-induced striatal dopamine depletion in B6CBA mice. |
| PubMed: | Protection against UVB irradiation by natural filters extracted from lichens. |
| PubMed: | Affinity profile at alpha(1)- and alpha(2)-adrenoceptor subtypes and in vitro cardiovascular actions of (+)-boldine. |
| PubMed: | Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity. |
| PubMed: | Protective effect of boldine on dopamine-induced membrane permeability transition in brain mitochondria and viability loss in PC12 cells. |
| PubMed: | Chemoprotective activity of boldine: modulation of drug-metabolizing enzymes. |
| PubMed: | Release of intermediate reactive hydrogen peroxide by macrophage cells activated by natural products. |
| PubMed: | Free-radical-induced inactivation of lysozyme and carbonyl residue generation in protein are not necessarily associated. |
| PubMed: | Protective effect of boldine on oxidative mitochondrial damage in streptozotocin-induced diabetic rats. |
| PubMed: | Protective effects of boldine against free radical-induced erythrocyte lysis. |
| PubMed: | Biological disposition of boldine: in vitro and in vivo studies. |
| PubMed: | Halogenated boldine derivatives with enhanced monoamine receptor selectivity. |
| PubMed: | Toxicological evaluation of the hydro-alcohol extract of the dry leaves of Peumus boldus and boldine in rats. |
| PubMed: | Boldine action against the stannous chloride effect. |
| PubMed: | Dry plant extracts loaded on fumed silica for direct compression: preparation and preformulation. |
| PubMed: | Halogenated derivatives of boldine with high selectivity for alpha1A-adrenoceptors in rat cerebral cortex. |
| PubMed: | Biochemical and behavioral effects of boldine and glaucine on dopamine systems. |
| PubMed: | Glaucine analogues as inhibitors of mouse splenocyte activity. |
| PubMed: | Antipoliovirus structure-activity relationships of some aporphine alkaloids. |
| PubMed: | Studies on neuromuscular blockade by boldine in the mouse phrenic nerve-diaphragm. |
| PubMed: | Effects of boldine on mouse diaphragm and sarcoplasmic reticulum vesicles isolated from skeletal muscle. |
| PubMed: | Inhibition of eukaryote protein kinases by isoquinoline and oxazine alkaloids. |
| PubMed: | Protective effect of boldine in experimental colitis. |
| PubMed: | Antiplatelet effects of some aporphine and phenanthrene alkaloids in rabbits and man. |
| PubMed: | A possible structural determinant of selectivity of boldine and derivatives for the alpha 1A-adrenoceptor subtype. |
| PubMed: | The effect of S-(+)-boldine on the alpha 1-adrenoceptor of the guinea-pig aorta. |
| PubMed: | Determination of lauraceous aporphine alkaloids by high-performance liquid chromatography. |
| PubMed: | Novel liquid chromatographic assay for the low-level determination of apomorphine in plasma. |
| PubMed: | Cytoprotective and antioxidant effects of boldine on tert-butyl hydroperoxide-induced damage to isolated hepatocytes. |
| PubMed: | Antiplatelet and vasorelaxing actions of some aporphinoids. |
| PubMed: | The inhibitory effects of boldine, glaucine, and probucol on TPA-induced down regulation of gap junction function. Relationships to intracellular peroxides, protein kinase C translocation, and connexin 43 phosphorylation. |
| PubMed: | Boldine prevents human liver microsomal lipid peroxidation and inactivation of cytochrome P4502E1. |
| PubMed: | Structure-antioxidative activity relationships in benzylisoquinoline alkaloids. |
| PubMed: | Anti-inflammatory and antipyretic effects of boldine. |
| PubMed: | Mechanisms of vasorelaxation induced by N-allylsecoboldine in rat thoracic aorta. |
| PubMed: | Effects of boldine on cellular immune functions in vitro. |
| PubMed: | Evaluation of the genotoxic potential of the alkaloid boldine in mammalian cell systems in vitro and in vivo. |
| PubMed: | Trypanocidal effect of boldine and related alkaloids upon several strains of Trypanosoma cruzi. |
| PubMed: | Determination of boldine in drug formulations by first-derivative synchronous spectrofluorimetry. |
| PubMed: | Boldo and boldine: an emerging case of natural drug development. |
| PubMed: | Iron-reducing and free-radical-scavenging properties of apomorphine and some related benzylisoquinolines. |
| PubMed: | Different mechanism of relaxation induced by aporphine alkaloids in rat uterus. |
| PubMed: | Determination of boldine in plasma by high-performance liquid chromatography. |
| PubMed: | Selective action of two aporphines at alpha 1-adrenoceptors and potential-operated Ca2+ channels. |
| PubMed: | Antioxidant action of benzylisoquinoline alkaloids. |
| PubMed: | Inhibition of rat liver microsomal lipid peroxidation by boldine. |
| PubMed: | Inhibition of nonenzymic lipid peroxidation by benzylisoquinoline alkaloids. |
| PubMed: | Activity of boldine on rat ileum. |
| PubMed: | Genotoxicity of the boldine aporphine alkaloid in prokaryotic and eukaryotic organisms. |
| PubMed: | Antioxidant properties of the alkaloid boldine in systems undergoing lipid peroxidation and enzyme inactivation. |
| PubMed: | Hepatoprotective and anti-inflammatory effects of a traditional medicinal plant of Chile, Peumus boldus. |
| PubMed: | Genotoxic effect of alkaloids. |
| PubMed: | A study of the adrenergic activity of the alkaloids boldine and glaucine. |
| PubMed: | Neuroleptic-like, anticonvulsant and antinociceptive effects of aporphine alkaloids: bulbocapnine, corytuberine, boldine and glaucine. |
| PubMed: | Alkaloids of Litsea wightiana1. |
| PubMed: | Voltammetric study of boldine on stationary platinum electrode. |
| PubMed: | Toxic alkaloids and their interaction with microsomal cytochrome P-450 in vitro. |
| PubMed: | [Determination of boldine by HPLC (high pressure liquid chromatography) in Boldus extracts]. |
| PubMed: | Biosynthesis of boldine (1,10-dimethoxy-6aalpha-aporphine-2,9-diol). |
| PubMed: | Fluorimetric analysis of alkaloids. Determination of serpentine, yohimbine, and boldine. |
| PubMed: | Stereochemical preferences for curarimimetic neuromuscular junction blockade I: enantiomeric monoquaternary amines as probes. |
| PubMed: | [Densitometric determination of boldine in boldo extracts]. |
| PubMed: | [Determination of boldine in Folium boldo and in the commercial preparation Boldiné Houdé]. |
| PubMed: | [A colored reaction of boldine]. |
| PubMed: | [Colorimetric determination of boldine]. |
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