d-coclaurine
sanjoinine K
Identification
| Name | d-coclaurine |
| CAS Number | 2196-60-3 |
| FDA UNII | Search |
| Molecular Formula | C17 H19 N O3 |
| Molecular Weight | 285.34303000 |
| Nikkaji Number | J36.682J |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 2657 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for d-coclaurine usage levels up to | not for fragrance use. |
| Recommendation for d-coclaurine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(1R)-1-[(4-
hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
sanjoinine K
PubMed:
Variation of the alkaloid content of Peumus boldus (boldo).
PubMed:
Determination of higenamine and coclaurine levels in human urine after the administration of a throat lozenge containing Nandina domestica fruit.
PubMed:
Computer-Aided
13
C NMR Chemical Profiling of Crude Natural Extracts without Fractionation.
PubMed:
Digital Gene Expression Analysis Provides Insight into the Transcript Profile of the Genes Involved in Aporphine Alkaloid Biosynthesis in Lotus (
Nelumbo nucifera
).
PubMed:
Cocculus hirsutus: Molecular Docking to Identify Suitable Targets for Hepatocellular Carcinoma by In silico Technique.
PubMed:
Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity.
PubMed:
Mining Enzyme Diversity of Transcriptome Libraries through DNA Synthesis for Benzylisoquinoline Alkaloid Pathway Optimization in Yeast.
PubMed:
Plant-like biosynthesis of isoquinoline alkaloids in Aspergillus fumigatus.
PubMed:
Cytochrome P450 2D6 and 3A4 enzyme inhibition by amine stimulants in dietary supplements.
PubMed:
Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum.
PubMed:
In vitro opioid receptor affinity and in vivo behavioral studies of Nelumbo nucifera flower.
PubMed:
Organocatalytic enantioselective Pictet-Spengler approach to biologically relevant 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloids.
PubMed:
[Chemical constituents of Cocculus orbiculatus var. mollis root].
PubMed:
[Cytotoxic alkaloids from stems of Nelumbo nucifera].
PubMed:
Ethnobotany, phytochemistry and pharmacology of Stephania rotunda Lour.
PubMed:
Antiplasmodial alkaloids from the bark of Cryptocarya nigra (Lauraceae).
PubMed:
Comparative transcriptome analysis using high papaverine mutant of Papaver somniferum reveals pathway and uncharacterized steps of papaverine biosynthesis.
PubMed:
Memory enhancement by traditional Chinese medicine?
PubMed:
Systematic silencing of benzylisoquinoline alkaloid biosynthetic genes reveals the major route to papaverine in opium poppy.
PubMed:
Heterologous protein production in Escherichia coli using the propionate-inducible pPro system by conventional and auto-induction methods.
PubMed:
Molecular cloning and characterization of CYP80G2, a cytochrome P450 that catalyzes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells.
PubMed:
Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy.
PubMed:
The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy.
PubMed:
Analysis of benzylisoquinoline-type alkaloids by electrospray tandem mass spectrometry and atmospheric pressure photoionization.
PubMed:
Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors.
PubMed:
Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids.
PubMed:
Evaluation of the mass spectrometric fragmentation of codeine and morphine after 13C-isotope biosynthetic labeling.
PubMed:
In vivo bioconversion of tetrahydroisoquinoline by recombinant coclaurine N-methyltransferase.
PubMed:
Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy.
PubMed:
Simplified tetrandrine congeners as possible antihypertensive agents with a dual mechanism of action.
PubMed:
Molecular cloning of columbamine O-methyltransferase from cultured Coptis japonica cells.
PubMed:
Molecular cloning and characterization of coclaurine N-methyltransferase from cultured cells of Coptis japonica.
PubMed:
Purification and characterization of coclaurine N-methyltransferase from cultured Coptis japonica cells.
PubMed:
Biosynthesis of Erythrina alkaloids in Erythrina crista-galli.
PubMed:
Antiplatelet of vasorelaxing actions of some benzylisoquinoline and phenanthrene alkaloids.
PubMed:
Structure-antioxidative activity relationships in benzylisoquinoline alkaloids.
PubMed:
Trypanocidal effect of boldine and related alkaloids upon several strains of Trypanosoma cruzi.
PubMed:
Bisbenzylisoquinoline alkaloids from Cyclea barbata.
PubMed:
Pharmacological studies on Aristolochia papillaris Mast. (Aristolochiaceae).
PubMed:
Antispasmodic activity of benzylisoquinoline alkaloids analogous to papaverine.
PubMed:
The purification and characterization of a unique cytochrome P-450 enzyme from Berberis stolonifera plant cell cultures.
PubMed:
Biosynthesis of bisbenzylisoquinoline alkaloids in cultured roots of Stephania cepharantha.
PubMed:
Inotropic effects of (+/-)-higenamine and its chemically related components, (+)-R-coclaurine and (+)-S-reticuline, contained in the traditional sino-Japanese medicines "bushi" and "shin-i" in isolated guinea pig papillary muscle.
PubMed:
Screening of isoquinoline alkaloids and their derivatives for antibacterial and antifungal activities.
PubMed:
Inhibition of metabolic response of polymorphonuclear leukocyte by biscoclaurine alkaloids.
PubMed:
Additional alkaloids of Pachygone ovata.
PubMed:
Effects of d-coclaurine and d-reticuline, benzyltetrahydroisoquinoline alkaloids, on levels of 3,4-dihydroxyphenylacetic acid and homovanillic acid in the mouse striatum.
PubMed:
[Effects of dl-demethyl coclaurine on beta-adrenergic receptors and adenylate cyclase in turkey erythrocyte membrane].
PubMed:
The neuromuscular blocking actions of coclaurine derivatives and of paeoniflorin derivatives.
PubMed:
Effects on central dopaminergic systems of d-coclaurine and d-reticuline, extracted from Magnolia salicifolia.
PubMed:
[Alkaloids of Annonaceae. XXIX. Alkaloids of Annona muricata].
PubMed:
Inhibition by biscoclaurine alkaloid of lipid peroxidation in biological membranes.
PubMed:
The isolation of stepharine and coclaurine from Sarcopetalum harveyanum.
PubMed:
Mass spectrometry of bisbenzylisoquinoline alkaloids. 3. Alkaloids derived from coclaurine units joined head-to-tail.
PubMed:
Mass spectrometry of bisbenzylisoquinoline alkaloids. II. Alkaloids derived from one coclaurine and one isococlaurine unit.
PubMed:
Mass spectrometry of bisbenzylisoquinoline alkaloids. I. Alkaloids derived from coclaurine units joined tail-to-tail.
PubMed:
The crystal structure of coclaurine hydrobromide monohydrate and the absolute configuration of coclaurine.
PubMed:
[Coclaurine and related compounds. II. Syntheses of 7-benzyloxy-1,2,3,4-tetrahydro-1-(p-hydroxyphenyl)-6-methoxy-2-methylisoquinoline and 7-benzyloxy-1,2,3,4-tetrahydro-1-(p-hydroxybenzyl)-6-methoxy-2-methyl-isoquinoline. (Studies on the syntheses of heterocyclic compounds. CLXXXV)].
PubMed:
[Coclaurine and related compounds. I. Syntheses of dl-coclaurine and dl-O-benzyl-N-methylcoclaurine. (Studies on the syntheses of heterocyclic compounds 103.)].
PubMed:
[Studies on the alkaloids of Formosan louraceous plants. II. Alkaloids of Machilus kusanoi Hayata. (2). The isolation of di-coclaurine].