Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.), is a small naturally occurring

hydroxycinnamic acid Hydroxycinnamic acids (hydroxycinnamates) are a class of aromatic acids or phenylpropanoids having a C6–C3 skeleton. These compounds are hydroxy derivatives of cinnamic acid. In the category of List of phytochemicals in food, phytochemicals tha ...

. It is a member of the

phenylpropanoid The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and ...

family. It is a commonly used matrix in MALDI

mass spectrometry Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is used ...

. It is a useful matrix for a wide variety of peptides and proteins. It serves well as a matrix for MALDI due to its ability to absorb

laser A laser is a device that emits light through a process of optical amplification based on the stimulated emission of electromagnetic radiation. The word ''laser'' originated as an acronym for light amplification by stimulated emission of radi ...

radiation and to also donate protons (H⁺) to the analyte of interest. 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. Sinapine is an alkaloidal amine found in black mustard seeds. It is considered a

choline Choline is a cation with the chemical formula . Choline forms various Salt (chemistry), salts, such as choline chloride and choline bitartrate. An essential nutrient for animals, it is a structural component of phospholipids and cell membrane ...

ester of sinapinic acid.

Natural occurrences

Sinapinic acid can be found in

wine Wine is an alcoholic drink made from Fermentation in winemaking, fermented fruit. Yeast in winemaking, Yeast consumes the sugar in the fruit and converts it to ethanol and carbon dioxide, releasing heat in the process. Wine is most often made f ...

vinegar Vinegar () is an aqueous solution of diluted acetic acid and trace compounds that may include flavorings. Vinegar typically contains from 5% to 18% acetic acid by volume. Usually, the acetic acid is produced by a double fermentation, converting ...

, and black plums.

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 Malic acid is an organic compound with the molecular formula . It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms ( ...

to produce D-

glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...

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,

References

{{Hydroxycinnamic acid O-methylated hydroxycinnamic acids Vinylogous carboxylic acids

Natural occurrences

Metabolism

Related compounds

See also

References