Sinapinic acid
Chemical compound
From Wikipedia, the free encyclopedia
Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.) is an organic compound with the formula (CH3O)2(HO)C6H2CH=CHCO2H. It is naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family, which includes many natural products.[1]
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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 | |
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CompTox Dashboard (EPA) |
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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).
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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 is 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.