Sinapine: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 447366952

| 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|changed|chemspider}}

| ChemSpiderID = 80576

| SMILES = O=C(/C=C/C1=CC(OC)=C(C(OC)=C1)O)OCC[N+](C)(C)C

| InChI = 1/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

| InChIKey = HUJXHFRXWWGYQH-IKLDFBCSAX

| StdInChI_Ref = {{stdinchicite|changed|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|changed|chemspider}}

| StdInChIKey = HUJXHFRXWWGYQH-UHFFFAOYSA-O

}}

|Section2={{Chembox Properties

| C=16 | H=24 | N=1 | O=5

| 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 =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

| HPhrases =

| PPhrases =

| GHS_ref =

'''Sinapine''' is an [[alkaloid]]al amine found in some seeds, particularly [[oil seeds]] of plants in the [[Family (biology)|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 [[Etienne 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 [[List of vegetable oils|oil crops]] and is plentiful in some types of [[press cake]] leftover after [[Expeller pressing|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>{{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 [[Degreasing|defatting]] the cake with [[hexane]] via a [[Soxhlet apparatus]] followed by extraction with 70% methanol held at 75&nbsp;°C.<ref>{{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>

== Metabolism ==

[[Sinapine esterase]] is an enzyme whose two substrates are sinapine and H₂O and whose two products are [[sinapic acid]] and [[choline]].

[[Sinapoylglucose—choline O-sinapoyltransferase]] is an enzyme whose two substrates are [[1-O-sinapoyl-beta-D-glucose|1-''O''-sinapoyl-β-<small>D</small>-glucose]] and [[choline]], whereas its two products are [[glucose|<small>D</small>-glucose]] and sinapine.

== See also ==

{{Div col|colwidth=16em}}

*[[Phenolic content in wine]]

*[[Syringaldehyde]]

*[[Syringol]]

*[[Syringic acid]]

*[[Acetosyringone]]

*[[Sinapyl alcohol]]

*[[Sinapinic acid]]

*[[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]]