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Revision as of 19:56, 29 August 2011 editNono64 (talk | contribs)Autopatrolled, Pending changes reviewers, Rollbackers96,246 editsm Matabolism section← Previous edit Latest revision as of 15:55, 23 January 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Added pmid. 
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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 447366952
| Name = Sinapine | Name = Sinapine
| ImageFile = Sinapine thiocyanate.PNG | ImageFile = Sinapine.svg
| ImageName = Chemical structure of sinapine
| ImageSize = 200px
| PIN = 2-{oxy}-''N'',''N'',''N''-trimethylethan-1-aminium
| ImageName = Chemical structure of sinapine thiocyanate
| OtherNames = Sinapoylcholine; Sinapic acid choline ester
| ImageAlt = Chemical structure of sinapine thiocyanate
|Section1={{Chembox Identifiers
| ImageCaption = Chemical structure of sinapine ]
| CASNo_Ref = {{cascite|correct|CAS}}
| IUPACName =
| CASNo = 18696-26-9
| OtherNames = Sinapoylcholine<!-- <br> -->
| UNII_Ref = {{fdacite|correct|FDA}}
|Section1= {{Chembox Identifiers
| CASNo = | UNII = 09211A0HHL
| CASNo_Ref = | CASNoOther =
| CASOther = | PubChem = 5280385
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| PubChem =
| SMILES = | ChemSpiderID = 80576
| SMILES = O=C(/C=C/C1=CC(OC)=C(C(OC)=C1)O)OCC(C)(C)C
| InChI =
| 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
| MeSHName = | MeSHName =
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=16 | H=24 | N=1 | O=5
| Formula = C<sub>16</sub>H<sub>24</sub>NO<sub>5</sub>
| MolarMass = 310.36 g/mol
| ExactMass = 310.165447 u
| Appearance = | Appearance =
| Density = | Density =
| MeltingPtC = 178
| MeltingPt = <!-- °C -->
| MeltingPt_ref = <ref>{{cite journal|last1=Gmelin|first1=R|last2=Bredenberg JB|first2=son|title=.|journal=Arzneimittel-Forschung|date=February 1966|volume=16|issue=2|pages=123–7|pmid=6014002|language=German}}</ref>
| BoilingPt = <!-- °C -->
| BoilingPt =
| Solubility = | Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| HPhrases =
| PPhrases =
| GHS_ref =
}} }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition =
| RPhrases = <!-- {{R10}}, {{R23}}, {{R34}}, {{R50}} etc. -->
| SPhrases = <!-- {{S1/2}}, {{S9}}, {{S16}}, {{S26}}, {{S36/37/39}}, {{S45}}, {{S61}} etc. -->
}} }}
}}
'''Sinapine''' is an alkaloidal amine found in ] seeds. It is considered a ] ester of ].


'''Sinapine''' is an ]al amine found in some seeds, particularly ] of plants in the ] ].<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 ] ester of ].
Sinapine was discovered by ] <!-- and ] -->in 1825.<ref>
Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline. Alexander Tzagoloff, Plant Physiol. 1963 March; 38(2), pp. 202–206, {{PMCID|PMC549906}}</ref>


Sinapine was discovered by ] <!-- and ] -->in 1825.<ref>{{Cite journal
==Metabolism==
| last1 = Tzagoloff | first1 = A.
] is an enzyme whose two substrates are sinapoylcholine (sinapine) and H<sub>2</sub>O and whose two products are sinapate (]) and ].
| 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==
] is an enzyme whose two substrates are ] and ], whereas its two products are ] and sinapoylcholine (sinapine).
Sinapine typically occurs in the outer seed coat of ] and is plentiful in some types of ] leftover after ].<ref name=CompRev /> Typical oil seed cake residues high in sinapine include '']'' (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 ] (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>


==References== ==Isolation==
The typical protocol for extracting Sinapine from seed cakes entails ] the cake with ] via a ] 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>
{{reflist}}


== Metabolism ==
]
] is an enzyme whose two substrates are sinapine and H<sub>2</sub>O and whose two products are ] and ].
]

] is an enzyme whose two substrates are ] and ], whereas its two products are ] and sinapine.

== See also ==
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== References ==
{{reflist}}


]
{{amine-stub}}
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