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 infludes 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,
[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, ] vinegar,
and black plums.
Sinapine id 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.
Related compounds
Canolol is a phenolic compound found in crude
canola oil. It is produced by decarboxylation of sinapic acid during canola seed roasting.
[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, ]
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.
See also
