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Sinapinic acid

Sinapic acid 3,5-Dimethoxy-4-hydroxycinnamic acid 4-Hydroxy-3,5-dimethoxycinnamic acid Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.) is an organic compound with the formula . It is naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family, which includes many natural products.

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). For example, it can be found in wine, vinegar, and black plums. Sinapine is found in black mustard seeds. It is considered a choline ester of sinapinic acid.

Sinapic acid has attracted much interest as an antioxidant

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.

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.

Research

Sinapic acid is a used in MALDI mass spectrometry. 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.

References

References

  1. (1999). "Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden". Journal of the Science of Food and Agriculture.
  2. (2014). "Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity". Comprehensive Reviews in Food Science and Food Safety.
  3. 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
  4. (1994). "Analysis of polyphenolic compounds of different vinegar samples". Zeitschrift für Lebensmittel-Untersuchung und -Forschung.
  5. (2022-08-02). "Determination of Phenolic Compounds and Bioactive Potential of Plum (Prunus salicina) Peel Extract Obtained by Ultrasound-Assisted Extraction". BioMed Research International.
  6. (1963). "Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline". Plant Physiology.
  7. (2002). "Rewriting the lignin roadmap". Current Opinion in Plant Biology.
  8. (2003). "Sinapate dehydrodimers and sinapate-ferulate heterodimers in cereal dietary fibre". J. Agric. Food Chem..
  9. 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
  10. (1989). "Matrix-assisted laser-desorption mass spectrometry using 355 nm radiation". Rapid Commun. Mass Spectrom..
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o-methylated-hydroxycinnamic-acids phenylogous-carboxylic-acids
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