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,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 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.

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

Phenolic content in wine Syringaldehyde Syringol Syringic acid Acetosyringone Sinapyl alcohol Sinapaldehyde Sinapine Canolol

References