Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Sinapinic acid: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 14:22, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 447513684 of page Sinapinic_acid for the Chem/Drugbox validation project (updated: '').  Latest revision as of 09:55, 19 May 2024 edit WikiCleanerBot (talk | contribs)Bots925,164 editsm v2.05b - Bot T20 CW#61 - Fix errors for CW project (Reference before punctuation)Tag: WPCleaner 
Line 1: Line 1:
{{cs1 config|name-list-style=vanc}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 444105125 | verifiedrevid = 464391904
| Name = Sinapinic acid | Name = Sinapinic acid
| ImageFile = sinapic acid.png | ImageFile = sinapic acid.png

<!-- | ImageSize = 200px -->
| ImageName = Sinapinic acid | ImageName = Sinapinic acid
| IUPACName = 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid | PIN = (2''E'')-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
| OtherNames = Sinapinic acid<br />Sinapic acid<br />3,5-Dimethoxy-4-hydroxycinnamic acid<br />4-Hydroxy-3,5-dimethoxycinnamic acid | OtherNames = Sinapinic acid<br />Sinapic acid<br />3,5-Dimethoxy-4-hydroxycinnamic acid<br />4-Hydroxy-3,5-dimethoxycinnamic acid
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 553361 | ChemSpiderID = 553361
| InChI = 1/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+ | InChI = 1/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+
Line 19: Line 19:
| StdInChIKey = PCMORTLOPMLEFB-ONEGZZNKSA-N | StdInChIKey = PCMORTLOPMLEFB-ONEGZZNKSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 530-59-6 | CASNo = 530-59-6
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 637775
| UNII = 68A28V6010
⚫ | PubChem = 637775
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 109341 | ChEMBL = 109341
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB08587 | DrugBank = DB08587
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
Line 29: Line 31:
| SMILES = COc1cc(cc(c1O)OC)/C=C/C(=O)O | SMILES = COc1cc(cc(c1O)OC)/C=C/C(=O)O
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>11</sub>H<sub>12</sub>O<sub>5</sub> | Formula = C<sub>11</sub>H<sub>12</sub>O<sub>5</sub>
| MolarMass = 224.21 g/mol | MolarMass = 224.21 g/mol
| MeltingPtC = 203 to 205
| ExactMass = 224.068473 u
| MeltingPt = 203-205 °C (decomposes) | MeltingPt_notes = (decomposes)
}} }}
}} }}
'''Sinapinic acid''', or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.), is a small naturally occurring ]. It is a member of the ] family. It is a commonly used matrix in ] ].<ref name="Beavis 1989">{{cite journal |vauthors=Beavis RC, Chait BT |title=Matrix-assisted laser-desorption mass spectrometry using 355 nm radiation |journal=Rapid Commun. Mass Spectrom. |volume=3 |issue=12 |pages=436–9 |year=1989 |pmid=2520224 |doi=10.1002/rcm.1290031208|bibcode=1989RCMS....3..436B }}</ref><ref name="Beavis 1989a">{{cite journal |vauthors=Beavis RC, Chait BT |title=Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins |journal=Rapid Commun. Mass Spectrom. |volume=3 |issue=12 |pages=432–5 |year=1989 |pmid=2520223 |doi=10.1002/rcm.1290031207|bibcode=1989RCMS....3..432B }}</ref> It is a useful matrix for a wide variety of peptides and proteins. It serves well as a matrix for MALDI due to its ability to absorb ] radiation and to also donate protons (H<sup>+</sup>) to the analyte of interest.

Sinapic acid can form dimers with itself (one structure) and ] (three different structures) in cereal cell walls and therefore may have a similar influence on cell-wall structure to that of the ].<ref name="Bunzel 2003">{{cite journal |vauthors=Bunzel M, Ralph J, Kim H, Lu F, Ralph SA, Marita JM, Hatfield RD, Steinhart H |title=Sinapate dehydrodimers and sinapate-ferulate heterodimers in cereal dietary fibre |journal=J. Agric. Food Chem. |volume=51 |pages=1427–1434 |year=2003 |doi=10.1021/jf020910v |pmid=12590493 |issue=5}}</ref>

] is an alkaloidal amine found in black mustard seeds. It is considered a ] ester of sinapinic acid.<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>

== Natural occurrences ==
Sinapinic acid can be found in ],<ref>Comparison of Phenolic Acids and Flavan-3-ols During Wine Fermentation of Grapes with Different Harvest Times. Rong-Rong Tian, Qiu-Hong Pan, Ji-Cheng Zhan, Jing-Ming Li, Si-Bao Wan, Qing-Hua Zhang and Wei-Dong Huang, Molecules, 2009, 14, pages 827-838, {{doi|10.3390/molecules14020827}}</ref> ],<ref>{{Cite journal | last1 = Gávez | first1 = M. C.| last2 = Barroso | first2 = C. G. A. | last3 = Péez-Bustamante | first3 = J. A. | title = Analysis of polyphenolic compounds of different vinegar samples | doi = 10.1007/BF01192948 | journal = Zeitschrift für Lebensmittel-Untersuchung und -Forschung | volume = 199 | pages = 29–31 | year = 1994 | s2cid = 91784893}}</ref> and black plums.<ref>{{Cite journal |last1=Jawad |first1=Muhammad |last2=Ali |first2=Moazzam |last3=Qasim |first3=Sadia |last4=Akbar |first4=Ali |last5=Khan |first5=Nazir Ahmad |last6=Sadiq |first6=Muhammad Bilal |date=2022-08-02 |title=Determination of Phenolic Compounds and Bioactive Potential of Plum (Prunus salicina) Peel Extract Obtained by Ultrasound-Assisted Extraction |journal=BioMed Research International |volume=2022 |pages=7787958 |doi=10.1155/2022/7787958 |doi-access=free |issn=2314-6133 |pmc=9433295 |pmid=36060132}}</ref>

== Metabolism ==
] is an enzyme that uses UDP-glucose and sinapate to produce UDP and ].

] is an enzyme that uses ] and (S)-] to produce D-] and ].

== Related compounds ==
] is a phenolic compound found in crude ]. It is produced by decarboxylation of sinapic acid during canola seed roasting.<ref>Antioxidant canolol production from a renewable feedstock via an engineered decarboxylase. Krista L. Morley, Stephan Grosse, Hannes Leischa and Peter C. K. Lau, Green Chem., 2013,n15, pages 3312-3317, {{doi|10.1039/C3GC40748A}}</ref>

== See also ==
{{Div col|colwidth=16em}}
*]
*]
*]
*]
*]
*]
*]
*]
*]
{{Div col end}}

== References ==
{{reflist}}

{{Hydroxycinnamic acid}}

]
]