{{chembox | Name = Sinapine | ImageFile = Sinapine.svg | ImageName = Chemical structure of sinapine | PIN = 2-{[(2''E'')-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-''N'',''N'',''N''-trimethylethan-1-aminium | OtherNames = Sinapoylcholine; Sinapic acid choline ester |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 18696-26-9 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 09211A0HHL | CASNoOther = | PubChem = 5280385 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 80576 | SMILES = O=C(/C=C/C1=CC(OC)=C(C(OC)=C1)O)OCC[N+](C)(C)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HUJXHFRXWWGYQH-UHFFFAOYSA-O | MeSHName = }} |Section2={{Chembox Properties | C=16 | H=24 | N=1 | O=5 | Appearance = | Density = | MeltingPtC = 178 | MeltingPt_ref = <ref>{{cite journal|last1=Gmelin|first1=R|last2=Bredenberg JB|first2=son|title=[Studies on the constituents of various Erysimum varieties: a) identification of the bitter substance erysimupicrone as strophanthidin; b) glucosinolates in the seeds of Erysimum perofskianum Fisch et Mey., E. Allionii hort., E. crepidifolium Rohb. and E. cheiranthoides L].|journal=Arzneimittel-Forschung|date=February 1966|volume=16|issue=2|pages=123–7|pmid=6014002|language=German}}</ref> | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | HPhrases = | PPhrases = | GHS_ref = }} }}
'''Sinapine''' is an alkaloidal amine found in some seeds, particularly oil seeds of plants in the family Brassicaceae.<ref name=CompRev>{{cite journal|last1=Niciforovic|first1=Neda|last2=Abramovi|first2=Helena|title=Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity|journal=Comprehensive Reviews in Food Science and Food Safety|date=2014|volume=13|issue=1|pages=34–51|doi=10.1111/1541-4337.12041|pmid=33412688 }}</ref> It is the choline ester of sinapic acid.
Sinapine was discovered by Étienne-Ossian Henry <!-- and Garot -->in 1825.<ref>{{Cite journal | last1 = Tzagoloff | first1 = A. | title = Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline | journal = Plant Physiology | volume = 38 | issue = 2 | pages = 202–206 | year = 1963 | pmid = 16655775 | pmc = 549906 | doi=10.1104/pp.38.2.202 }}</ref>
==Occurrence== Sinapine typically occurs in the outer seed coat of oil crops and is plentiful in some types of press cake leftover after vegetable oil extraction.<ref name=CompRev /> Typical oil seed cake residues high in sinapine include ''Brassica juncea'' (1.22% by mass),<ref>{{cite journal|last1=Matthäus|first1=B .|last2=Zubr|first2=J.|title=Variability of specific components in Camelina sativa oilseed cakes|journal=Industrial Crops and Products|date=2000|volume=12|issue=1|pages=9–18|doi=10.1016/S0926-6690(99)00040-0}}</ref> and rapeseed (0.39-1.06% by mass).<ref name=Vuorela>{{cite book|last1=Vuorela|first1=Satu|title=Analysis, isolation, and bioactivities of rapeseed phenolics|date=2005|publisher=University of Helsinki|location=Helsinki, Finland|isbn=9789521027215|pages=19–20|url=https://helda.helsinki.fi/bitstream/handle/10138/20877/analysis.pdf?sequence=1|accessdate=14 June 2014}}</ref>
==Isolation== The typical protocol for extracting sinapine from seed cakes entails defatting the cake with hexane via a Soxhlet apparatus followed by extraction with 70% methanol held at 75 °C.<ref name=Vuorela/>
== Biosynthesis and metabolism == The enzyme sinapoylglucose—choline O-sinapoyltransferase, characterised from radish and white mustard, converts 1-O-sinapoyl-beta-D-glucose and choline to sinapine.<ref>{{cite journal |last1=Gräwe |first1=Walter |last2=Strack |first2=Dieter |title=Partial Purification and Some Properties of 1-Sinapoylglucose: Choline Sinapoyltransferase ("Sinapine Synthase") from Seeds of ''Raphanus sativus'' L. and ''Sinapis alba'' L |journal=Zeitschrift für Naturforschung C |date=1986 |volume=41 |issue=1–2 |pages=28–33 |doi=10.1515/znc-1986-1-206 |doi-access=free }}</ref> The same transformation occurs in rapeseed.<ref>{{cite journal |last1=Vogt |first1=T. |last2=Aebershold |first2=R. |last3=Ellis |first3=B. |title=Purification and Characterization of Sinapine Synthase from Seeds of ''Brassica napus'' |journal=Archives of Biochemistry and Biophysics |date=1993 |volume=300 |issue=2 |pages=622–628 |doi=10.1006/abbi.1993.1086 |pmid=8382030 }}</ref>
{{chemrxn|width=70%| {{chemrxn/cpd|qid=Q27101966|caption=1-O-sinapoyl-beta-D-glucose }} {{chemrxn/txt|+ }} {{chemrxn/cpd|choline|upright=0.5 }} {{chemrxn/arw| }} {{chemrxn/cpd|sinapine }} {{chemrxn/txt|+ }} {{chemrxn/cpd|qid=Q23905964|caption=D-glucose|upright=0.5 }} }}
The enzyme sinapine esterase from radish can metabolise sinapine by hydrolysis to sinapinic acid and choline:<ref>{{cite journal |last1=Nurmann |first1=Gerhild |last2=Strack |first2=Dieter |title=Sinapine Esterase I. Characterization of Sinapine Esterase from Cotyledons of ''Raphanus sativus'' |journal=Zeitschrift für Naturforschung C |date=1979 |volume=34 |issue=9–10 |pages=715–720 |doi=10.1515/znc-1979-9-1011 |doi-access=free }}</ref>
{{chemrxn|width=70%| {{chemrxn/cpd|sinapine|upright=1.2 }} {{chemrxn/arw|fwd_in={{chem2|H2O}} }} {{chemrxn/cpd|sinapinic acid }} {{chemrxn/txt|+ }} {{chemrxn/cpd|choline|upright=0.5 }} }}
== See also == {{Div col|colwidth=16em}} *Phenolic content in wine *Syringaldehyde *Syringol *Syringic acid *Acetosyringone *Sinapyl alcohol *Sinapaldehyde *Canolol {{Div col end}}
== References == {{reflist}}
Category:Alkaloids Category:Quaternary ammonium compounds Category:Hydroxycinnamic acid esters Category:O-methylated hydroxycinnamic acids Category:Resorcinol ethers