Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.), is a small naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family. It is a commonly used matrix in MALDImass spectrometry.[1][2] 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 laser radiation and to also donate protons (H+) to the analyte of interest.
Sinapic acid can form dimers with itself (one structure) and ferulic acid (three different structures) in cereal cell walls and therefore may have a similar influence on cell-wall structure to that of the diferulic acids.[3]
Sinapine is an alkaloidal amine found in black mustard seeds. It is considered a choline ester of sinapinic acid.[4]
^Beavis RC, Chait BT (1989). "Matrix-assisted laser-desorption mass spectrometry using 355 nm radiation". Rapid Commun. Mass Spectrom. 3 (12): 436–9. Bibcode:1989RCMS....3..436B. doi:10.1002/rcm.1290031208. PMID 2520224.
^Beavis RC, Chait BT (1989). "Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins". Rapid Commun. Mass Spectrom. 3 (12): 432–5. Bibcode:1989RCMS....3..432B. doi:10.1002/rcm.1290031207. PMID 2520223.
^Bunzel M, Ralph J, Kim H, Lu F, Ralph SA, Marita JM, Hatfield RD, Steinhart H (2003). "Sinapate dehydrodimers and sinapate-ferulate heterodimers in cereal dietary fibre". J. Agric. Food Chem. 51 (5): 1427–1434. doi:10.1021/jf020910v. PMID 12590493.
^Tzagoloff A (1963). "Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline". Plant Physiology. 38 (2): 202–206. doi:10.1104/pp.38.2.202. PMC549906. PMID 16655775.
^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
^Gávez MC, Barroso CG, Péez-Bustamante JA (1994). "Analysis of polyphenolic compounds of different vinegar samples". Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 199: 29–31. doi:10.1007/BF01192948. S2CID 91784893.
^Jawad M, Ali M, Qasim S, Akbar A, Khan NA, Sadiq MB (2022-08-02). "Determination of Phenolic Compounds and Bioactive Potential of Plum (Prunus salicina) Peel Extract Obtained by Ultrasound-Assisted Extraction". BioMed Research International. 2022: 7787958. doi:10.1155/2022/7787958. ISSN 2314-6133. PMC9433295. PMID 36060132.
^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
January 01, 1970
sinapinic, acid, sinapic, acid, sinapine, origin, sinapi, sinapis, mustard, sinapine, small, naturally, occurring, hydroxycinnamic, acid, member, phenylpropanoid, family, commonly, used, matrix, maldi, mass, spectrometry, useful, matrix, wide, variety, peptide. Sinapinic acid or sinapic acid Sinapine Origin L Sinapi sinapis mustard Gr cf F Sinapine is a small naturally occurring hydroxycinnamic acid It is a member of the phenylpropanoid family It is a commonly used matrix in MALDI mass spectrometry 1 2 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 laser radiation and to also donate protons H to the analyte of interest Sinapinic acid Names Preferred IUPAC name 2E 3 4 Hydroxy 3 5 dimethoxyphenyl prop 2 enoic acid Other names Sinapinic acidSinapic acid3 5 Dimethoxy 4 hydroxycinnamic acid4 Hydroxy 3 5 dimethoxycinnamic acid Identifiers CAS Number 530 59 6 Y 3D model JSmol Interactive image ChEBI CHEBI 15714 Y ChEMBL ChEMBL109341 Y ChemSpider 553361 Y DrugBank DB08587 Y PubChem CID 637775 UNII 68A28V6010 Y CompTox Dashboard EPA DTXSID40862129 InChI InChI 1S 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 YKey PCMORTLOPMLEFB ONEGZZNKSA N YInChI 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 Key PCMORTLOPMLEFB ONEGZZNKBS SMILES COc1cc cc c1O OC C C C O O Properties Chemical formula C11H12O5 Molar mass 224 21 g mol Melting point 203 to 205 C 397 to 401 F 476 to 478 K decomposes Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Sinapic acid can form dimers with itself one structure and ferulic acid three different structures in cereal cell walls and therefore may have a similar influence on cell wall structure to that of the diferulic acids 3 Sinapine is an alkaloidal amine found in black mustard seeds It is considered a choline ester of sinapinic acid 4 Contents 1 Natural occurrences 2 Metabolism 3 Related compounds 4 See also 5 ReferencesNatural occurrences editSinapinic acid can be found in wine 5 vinegar 6 and black plums 7 Metabolism editSinapate 1 glucosyltransferase is an enzyme that uses UDP glucose and sinapate to produce UDP and 1 sinapoyl D glucose Sinapoylglucose malate O sinapoyltransferase is an enzyme that uses 1 O sinapoyl beta D glucose and S malate to produce D glucose and sinapoyl S malate Related compounds editCanolol is a phenolic compound found in crude canola oil It is produced by decarboxylation of sinapic acid during canola seed roasting 8 See also editPhenolic content in wine Syringaldehyde Syringol Syringic acid Acetosyringone Sinapyl alcohol Sinapaldehyde Sinapine CanololReferences edit Beavis RC Chait BT 1989 Matrix assisted laser desorption mass spectrometry using 355 nm radiation Rapid Commun Mass Spectrom 3 12 436 9 Bibcode 1989RCMS 3 436B doi 10 1002 rcm 1290031208 PMID 2520224 Beavis RC Chait BT 1989 Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins Rapid Commun Mass Spectrom 3 12 432 5 Bibcode 1989RCMS 3 432B doi 10 1002 rcm 1290031207 PMID 2520223 Bunzel M Ralph J Kim H Lu F Ralph SA Marita JM Hatfield RD Steinhart H 2003 Sinapate dehydrodimers and sinapate ferulate heterodimers in cereal dietary fibre J Agric Food Chem 51 5 1427 1434 doi 10 1021 jf020910v PMID 12590493 Tzagoloff A 1963 Metabolism of Sinapine in Mustard Plants I Degradation of Sinapine into Sinapic Acid amp Choline Plant Physiology 38 2 202 206 doi 10 1104 pp 38 2 202 PMC 549906 PMID 16655775 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 Gavez MC Barroso CG Peez Bustamante JA 1994 Analysis of polyphenolic compounds of different vinegar samples Zeitschrift fur Lebensmittel Untersuchung und Forschung 199 29 31 doi 10 1007 BF01192948 S2CID 91784893 Jawad M Ali M Qasim S Akbar A Khan NA Sadiq MB 2022 08 02 Determination of Phenolic Compounds and Bioactive Potential of Plum Prunus salicina Peel Extract Obtained by Ultrasound Assisted Extraction BioMed Research International 2022 7787958 doi 10 1155 2022 7787958 ISSN 2314 6133 PMC 9433295 PMID 36060132 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 Retrieved from https en wikipedia org w index php title Sinapinic acid amp oldid 1214804009, wikipedia, wiki, book, books, library,
