# Sinapine

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> Markdown URL: https://mediated.wiki/source/Sinapine.md
> Source: https://en.wikipedia.org/wiki/Sinapine
> Source revision: 1356014274
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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 [alkaloid](/source/alkaloid)al amine found in some seeds, particularly [oil seeds](/source/oil_seeds) of plants in the [family](/source/Family_(taxonomy)) [Brassicaceae](/source/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](/source/choline) ester of [sinapic acid](/source/sinapic_acid).

Sinapine was discovered by [Étienne-Ossian Henry](/source/%C3%89tienne-Ossian_Henry) <!-- and [Garot](/source/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](/source/List_of_vegetable_oils) and is plentiful in some types of [press cake](/source/press_cake) leftover after [vegetable oil extraction](/source/Expeller_pressing).<ref name=CompRev /> Typical oil seed cake residues high in sinapine include ''[Brassica juncea](/source/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](/source/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](/source/Degreasing) the cake with [hexane](/source/hexane) via a [Soxhlet apparatus](/source/Soxhlet_apparatus) followed by extraction with 70% methanol held at 75&nbsp;°C.<ref name=Vuorela/>

== Biosynthesis and metabolism ==
The enzyme [sinapoylglucose—choline O-sinapoyltransferase](/source/sinapoylglucose%E2%80%94choline_O-sinapoyltransferase), characterised from [radish](/source/radish) and [white mustard](/source/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](/source/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](/source/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](/source/D-glucose)|upright=0.5 }}
}}

The enzyme [sinapine esterase](/source/sinapine_esterase) from radish can metabolise sinapine by [hydrolysis](/source/hydrolysis) to [sinapinic acid](/source/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](/source/Phenolic_content_in_wine)
*[Syringaldehyde](/source/Syringaldehyde)
*[Syringol](/source/Syringol)
*[Syringic acid](/source/Syringic_acid)
*[Acetosyringone](/source/Acetosyringone)
*[Sinapyl alcohol](/source/Sinapyl_alcohol)
*[Sinapaldehyde](/source/Sinapaldehyde)
*[Canolol](/source/Canolol)
{{Div col end}}

== References ==
{{reflist}}

Category:Alkaloids
Category:Quaternary ammonium compounds
Category:Hydroxycinnamic acid esters
Category:O-methylated hydroxycinnamic acids
Category:Resorcinol ethers

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Adapted from the Wikipedia article [Sinapine](https://en.wikipedia.org/wiki/Sinapine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Sinapine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.