Chemistry:Sinapinic acid
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| Names | |
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| Preferred IUPAC name
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid | |
| Other names
Sinapinic acid
Sinapic acid 3,5-Dimethoxy-4-hydroxycinnamic acid 4-Hydroxy-3,5-dimethoxycinnamic acid | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| 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). | |
 verify (what is   ?)
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| Infobox references | |
Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.) is an organic compound with the formula (CH
3O)
2(HO)C
6H
2CH=CHCO
2H.
It is naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family, which includes many natural products.[1]
Natural occurrences
Sinapic acid is found widely in plants including those used for human nutrition. Some common sinapic acid conjugates include esters with malate and choline (sinapine). [2] For example, it can be found in wine,[3] vinegar,[4] and black plums.[5] Sinapine id found in black mustard seeds. It is considered a choline ester of sinapinic acid.[6]
Sinapic acid has attracted much interest as an antioxidant[7]
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.[8]
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.[9]
Research
Sinapic acid is a used in MALDI mass spectrometry.[10] 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.
See also
References
- ↑ "Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden". Journal of the Science of Food and Agriculture 79 (3): 362–372. 1999. doi:10.1002/(sici)1097-0010(19990301)79:3<362::aid-jsfa256>3.0.co;2-d. Bibcode: 1999JSFA...79..362C.
- ↑ Nićiforović, Neda; Abramovič, Helena (2014). "Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity". Comprehensive Reviews in Food Science and Food Safety 13 (1): 34–51. doi:10.1111/1541-4337.12041. PMID 33412688.
- ↑ 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 für Lebensmittel-Untersuchung und -Forschung 199: 29–31. doi:10.1007/BF01192948.
- ↑ Jawad, Muhammad; Ali, Moazzam; Qasim, Sadia; Akbar, Ali; Khan, Nazir Ahmad; Sadiq, Muhammad Bilal (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. doi:10.1155/2022/7787958. ISSN 2314-6133. PMID 36060132.
- ↑ 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. PMID 16655775.
- ↑ Humphreys, John M.; Chapple, Clint (2002). "Rewriting the lignin roadmap". Current Opinion in Plant Biology 5 (3): 224–229. doi:10.1016/s1369-5266(02)00257-1. PMID 11960740. Bibcode: 2002COPB....5..224H.
- ↑ "Sinapate dehydrodimers and sinapate-ferulate heterodimers in cereal dietary fibre". J. Agric. Food Chem. 51 (5): 1427–1434. 2003. doi:10.1021/jf020910v. PMID 12590493.
- ↑ 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
- ↑ "Matrix-assisted laser-desorption mass spectrometry using 355 nm radiation". Rapid Commun. Mass Spectrom. 3 (12): 436–9. 1989. doi:10.1002/rcm.1290031208. PMID 2520224. Bibcode: 1989RCMS....3..436B.
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