d-coclaurine

sanjoinine K

CAS: 2196-60-3 C17 H19 N O3 MW: 285.34303000

Identification

Named-coclaurine
CAS Number2196-60-3
FDA UNIISearch
Molecular FormulaC17 H19 N O3
Molecular Weight285.34303000
Nikkaji NumberJ36.682J

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 ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for d-coclaurine usage levels up tonot for fragrance use.
Recommendation for d-coclaurine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

soursop plant

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].