sinapine
ethanaminium, 2-[[3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl]oxy]-N,N,N-trimethyl-
Identification
| Name | sinapine |
| IUPAC | 2-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxyethyl-trimethylazanium |
| CAS Number | 18696-26-9 |
| FDA UNII | 09211A0HHL |
| Molecular Formula | C16 H24 N O5 |
| Molecular Weight | 310.37028000 |
| Beilstein | 4933491 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Flash Point | 32.00 °F. TCC ( 0.00 °C. ) (est) |
| logP (o/w) | -3.370 (est) |
| Soluble in | water, 6398 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 sinapine usage levels up to | not for fragrance use. |
| Recommendation for sinapine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
ethanaminium, 2-((3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)oxy)-N,N,N-trimethyl-
ethanaminium, 2-[[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl]oxy]-N,N,N-trimethyl-
ethanaminium, 2-[[3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl]oxy]-N,N,N-trimethyl-
4-
hydroxy-3,5-dimethoxycinnamate choline
2-(4-
hydroxy-3,5-dimethoxycinnamoyloxy)-N,N,N-trimethylethanaminium
2-((3-(4-
hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)oxy)-N,N,N-trimethyl ethanaminium
2-((3-(4-
hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)oxy)-N,N,N-trimethylethanaminium
2-[[3-(4-
hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl]oxy]-N,N,N-trimethylethanaminium
2-{[3-(4-
hydroxy-3,5-dimethoxyphenyl)acryloyl]oxy}-N,N,N-trimethylethanaminium
2-{[(2E)-3-(4-
hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-N,N,N-trimethylethanaminium
2-[(E)-3-(4-
hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxyethyl-trimethylazanium
2-[(2E)-3-(4-
hydroxy-3,5-dimethoxyphenyl)prop-2-enoyloxy]-N,N,N-trimethylethanaminium
sinapic acid choline ester
sinapine bisulphate
sinapoylcholine
O-
sinapoylcholine
PubMed:
Value-added potential of expeller-pressed canola oil refining: characterization of sinapic Acid derivatives and tocopherols from byproducts.
PubMed:
Sinapine as an active compound for inhibiting the proliferation of Caco-2 cells via downregulation of P-glycoprotein.
PubMed:
Influence of microwaves treatment of rapeseed on phenolic compounds and canolol content.
PubMed:
Evaluation of Camelina sativa (L.) Crantz meal as an alternative protein source in ruminant rations.
PubMed:
Skin penetration of topically applied white mustard extract and its effects on epidermal Langerhans cells and cytokines.
PubMed:
Genetic enhancement of Brassica napus seed quality.
PubMed:
Biophenols and antioxidant properties of Australian canola meal.
PubMed:
Antioxidant extraction from mustard (Brassica juncea) seed meal using high-intensity ultrasound.
PubMed:
Phenolic composition analysis and gene expression in developing seeds of yellow- and black-seeded Brassica napus.
PubMed:
Reprogramming the phenylpropanoid metabolism in seeds of oilseed rape by suppressing the orthologs of reduced epidermal fluorescence1.
PubMed:
Combined fibroblast growth factor receptor 4 cell membrane chromatography online with high performance liquid chromatography/mass spectrometry to screen active compounds in Brassica albla.
PubMed:
Tissue-specific distribution of secondary metabolites in rapeseed (Brassica napus L.).
PubMed:
Metabolic profiling of lignans and other secondary metabolites from rapeseed ( Brassica napus L.).
PubMed:
Factors that affect the nutritive value of canola meal for poultry.
PubMed:
Profile and distribution of soluble and insoluble phenolics in Chinese rapeseed (Brassica napus).
PubMed:
[Synthesis of seven sinapine analogs and their effects on the tension of smooth muscle of intestines isolated from rabbit].
PubMed:
A mutation screening platform for rapeseed (Brassica napus L.) and the detection of sinapine biosynthesis mutants.
PubMed:
Chemical composition, antioxidant and antimicrobial properties of Rapa Catozza Napoletana (Brassica rapa L. var. rapa DC.) seed meal, a promising protein source of Campania region (southern Italy) horticultural germplasm.
PubMed:
Effects of sinapic Acid of 4 vessel occlusion model-induced ischemia and cognitive impairments in the rat.
PubMed:
Sinapine detection in radish taproot using surface desorption atmospheric pressure chemical ionization mass spectrometry.
PubMed:
Overexpression of sinapine esterase BnSCE3 in oilseed rape seeds triggers global changes in seed metabolism.
PubMed:
Profiling of phenylpropanoids in transgenic low-sinapine oilseed rape (Brassica napus).
PubMed:
Sinapate esters in brassicaceous plants: biochemistry, molecular biology, evolution and metabolic engineering.
PubMed:
The effect of chemically and hydrothermally treated rapeseed on the performance and thyroid parameters of layers.
PubMed:
Determination of Sinapic Acid Derivatives in Canola Extracts Using High-Performance Liquid Chromatography.
PubMed:
Genomic microstructure and differential expression of the genes encoding UDP-glucose:sinapate glucosyltransferase (UGT84A9) in oilseed rape (Brassica napus).
PubMed:
Metabolic and bioactivity insights into Brassica oleracea var. acephala.
PubMed:
Pleiotropic changes in Arabidopsis f5h and sct mutants revealed by large-scale gene expression and metabolite analysis.
PubMed:
Targeted modulation of sinapine biosynthesis pathway for seed quality improvement in Brassica napus.
PubMed:
[Inhibitory effects of sinapine on activity of acetylcholinesterase in cerebral homogenate and blood serum of rats].
PubMed:
The role of UDP-glucose:hydroxycinnamate glucosyltransferases in phenylpropanoid metabolism and the response to UV-B radiation in Arabidopsis thaliana.
PubMed:
Manipulation of sinapine, choline and betaine accumulation in Arabidopsis seed: towards improving the nutritional value of the meal and enhancing the seedling performance under environmental stresses in oilseed crops.
PubMed:
Nutritional and physiological effects of dietary sinapic acid (4-hydroxy-3,5-dimethoxy-cinnamic acid) in broiler chickens and its metabolism in the digestive tract.
PubMed:
QTL for phytosterol and sinapate ester content in Brassica napus L. collocate with the two erucic acid genes.
PubMed:
Role of a GDSL lipase-like protein as sinapine esterase in Brassicaceae.
PubMed:
The genes BnSCT1 and BnSCT2 from Brassica napus encoding the final enzyme of sinapine biosynthesis: molecular characterization and suppression.
PubMed:
[Study of distribution of sinapine in commonly used crude drugs from cruciferous plants].
PubMed:
Ontogenic profiling of glucosinolates, flavonoids, and other secondary metabolites in Eruca sativa (salad rocket), Diplotaxis erucoides (wall rocket), Diplotaxis tenuifolia (wild rocket), and Bunias orientalis (Turkish rocket).
PubMed:
Resveratrol glucoside (Piceid) synthesis in seeds of transgenic oilseed rape (Brassica napus L.).
PubMed:
The tu8 mutation of Arabidopsis thaliana encoding a heterochromatin protein 1 homolog causes defects in the induction of secondary metabolite biosynthesis.
PubMed:
Formation of a complex pattern of sinapate esters in Brassica napus seeds, catalyzed by enzymes of a serine carboxypeptidase-like acyltransferase family?
PubMed:
Electrochemistry of sinapine and its detection in medicinal plants.
PubMed:
Effect of dehulling of rapeseed on feed value and nutrient digestibility of rape products in pigs.
PubMed:
Molecular regulation of sinapate ester metabolism in Brassica napus: expression of genes, properties of the encoded proteins and correlation of enzyme activities with metabolite accumulation.
PubMed:
Screening crucifer seeds as sources of specific intact glucosinolates using ion-pair high-performance liquid chromatography negative ion electrospray mass spectrometry.
PubMed:
Arabidopsis CYP98A3 mediating aromatic 3-hydroxylation. Developmental regulation of the gene, and expression in yeast.
PubMed:
Antioxidant activity of extracts obtained from residues of different oilseeds.
PubMed:
High performance liquid chromatography of phenolic choline ester fragments derived by chemical and enzymatic fragmentation processes: analysis of sinapine in rape seed.
PubMed:
Phenolics and physico-chemical characteristics of persimmon during post-harvest storage.
PubMed:
Application and Evaluation of Ion-Exchange UV Spectrophotometric Method for Determination of Sinapine in Brassica Seeds and Meals.
PubMed:
Identification of a CYP84 family of cytochrome P450-dependent mono-oxygenase genes in Brassica napus and perturbation of their expression for engineering sinapine reduction in the seeds.
PubMed:
Transformation of 3,5-dimethoxy,4-hydroxy cinnamic acid by polyphenol oxidase from the fungus Trametes versicolor: product elucidation studies.
PubMed:
Comparison of 3 methods for the determination of sinapic acid ester content in enzymatically treated canola meals.
PubMed:
[Radiation protection effects of sinapine on Drosophila melanogaster in a sex-linked recessive lethal test system].
PubMed:
Purification and characterization of sinapine synthase from seeds of Brassica napus.
PubMed:
Sinapoylglucose: malate sinapoyltransferase activity in seeds and seedlings of rape.
PubMed:
Valorization of rapeseed meal. 5. Effects of sinapine and other phenolic compounds on food intake and nutrient utilization in growing rats.
PubMed:
The voluntary food intake by growing pigs of diets containing 'treated' rapeseed meals or extracts of rapeseed meal.
PubMed:
Voluntary food intake of growing pigs given diets containing rapeseed meal, from different types and varieties of rape, as the only protein supplement.
PubMed:
The assessment of a new protein source--rapeseed.
PubMed:
[Quantitative procedure for determination of sinapine (author's transl)].
PubMed:
Rapeseed meal and egg taint: the role of sinapine.
PubMed:
Influence of sinapine and p-hydroxybenzylglucosinolate on the nutritional value of rapeseed and white mustard meals.
PubMed:
Metabolism of Sinapine in Mustard Plants. II. Purification & Some Properties of Sinapine Esterase.
PubMed:
Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline.