Sinapinic acid
| Sinapinic acid | |
|---|---|
 | |
| IUPAC name 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid | |
| Other names Sinapinic acid | |
| Identifiers | |
| CAS number | 530-59-6  |
| PubChem | 637775 |
| ChemSpider | 553361 |
| DrugBank | DB08587 |
| ChEBI | CHEBI:15714 |
| ChEMBL | CHEMBL109341 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C11H12O5 |
| Molar mass | 224.21 g/mol |
| Melting point | 203–205 °C (decomposes) |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
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.
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 sinapic acid.[4]
Natural occurrences
Sinapinic acid can be found in wine[5] and vinegar.[6]
Metabolism
sinapate 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
Canolol is a phenolic compound found in crude canola oil. It is produced by decarboxylation of sinapic acid during canola seed roasting.[7]
See also
References
- ↑ Beavis RC, Chait BT (1989). "Matrix-assisted laser-desorption mass spectrometry using 355 nm radiation". Rapid Commun. Mass Spectrom. 3 (12): 436–9. 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. 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. 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
- ↑ Gávez, M. C.; Barroso, C. G. A.; Péez-Bustamante, J. A. (1994). "Analysis of polyphenolic compounds of different vinegar samples". Zeitschrift fur Lebensmittel-Untersuchung und -Forschung 199: 29. doi:10.1007/BF01192948.
- ↑ 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
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