EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes

ethanaminium, 2-[[3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl]oxy]-N,N,N-trimethyl-

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CAS Number: 18696-26-9Picture of molecule3D/inchi
Beilstein Number:4933491
XlogP3-AA:1.80 (est)
Molecular Weight:310.37028000
Formula:C16 H24 N O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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US Patents:Search
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Pubchem Patents:Search
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)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
Alfa Biotechnology
For experimental / research use only.
Sinapine 99%
BOC Sciences
For experimental / research use only.
Ethanaminium,2-[[3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl]oxy]-N,N,N-trimethyl- 95%
Safety Information:
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
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.
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5280385
National Institute of Allergy and Infectious Diseases:Data
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5280385
Pubchem (sid):135066854
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C00933
HMDB (The Human Metabolome Database):HMDB29379
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 cress garden cress
Search Trop Picture
 mustard black mustard
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 mustard white mustard
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 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-((3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)oxy)-N,N,N-trimethyl ethanaminium
 sinapic acid choline ester
 sinapine bisulphate


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.
black mustard seeds, seeds of brassica nigra. Alkaloid from seeds of black mustard (Brassica nigra), white mustard (Sinapis alba) and many other spp. in the Cruciferae Storage protein isol. from the seeds of Brassica napus (rape)
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