Sinapinic acid

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Sinapinic acid
Sinapic acid.png
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
PubChem CID
UNII
  • InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+ Yes check.svgY
    Key: PCMORTLOPMLEFB-ONEGZZNKSA-N Yes check.svgY
  • InChI=1/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+
    Key: PCMORTLOPMLEFB-ONEGZZNKBS
  • COc1cc(cc(c1O)OC)/C=C/C(=O)O
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.), is a small naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family. It is a commonly used matrix in MALDI mass spectrometry. [1] [2] 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 radiation and to also donate protons (H+) to the analyte of interest.

Contents

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. [3]

Sinapine is an alkaloidal amine found in black mustard seeds. It is considered a choline ester of sinapinic acid. [4]

Natural occurrences

Sinapinic acid can be found in wine [5] and vinegar. [6]

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.

Canolol is a phenolic compound found in crude canola oil. It is produced by decarboxylation of sinapic acid during canola seed roasting. [7]

See also

Related Research Articles

<span class="mw-page-title-main">Koichi Tanaka</span> Japanese electrical engineer (born 1959)

Koichi Tanaka is a Japanese electrical engineer who shared the Nobel Prize in Chemistry in 2002 for developing a novel method for mass spectrometric analyses of biological macromolecules with John Bennett Fenn and Kurt Wüthrich.

<span class="mw-page-title-main">Matrix-assisted laser desorption/ionization</span> Ionization technique

In mass spectrometry, matrix-assisted laser desorption/ionization (MALDI) is an ionization technique that uses a laser energy-absorbing matrix to create ions from large molecules with minimal fragmentation. It has been applied to the analysis of biomolecules and various organic molecules, which tend to be fragile and fragment when ionized by more conventional ionization methods. It is similar in character to electrospray ionization (ESI) in that both techniques are relatively soft ways of obtaining ions of large molecules in the gas phase, though MALDI typically produces far fewer multi-charged ions.

<span class="mw-page-title-main">Caffeic acid</span> Chemical compound

Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is an intermediate in the biosynthesis of lignin, one of the principal components of woody plant biomass and its residues.

<span class="mw-page-title-main">History of mass spectrometry</span>

The history of mass spectrometry has its roots in physical and chemical studies regarding the nature of matter. The study of gas discharges in the mid 19th century led to the discovery of anode and cathode rays, which turned out to be positive ions and electrons. Improved capabilities in the separation of these positive ions enabled the discovery of stable isotopes of the elements. The first such discovery was with the element neon, which was shown by mass spectrometry to have at least two stable isotopes: 20Ne and 22Ne. Mass spectrometers were used in the Manhattan Project for the separation of isotopes of uranium necessary to create the atomic bomb.

<span class="mw-page-title-main">Sinapyl alcohol</span> Chemical compound

Sinapyl alcohol is an organic compound structurally related to cinnamic acid. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. This phytochemical is one of the monolignols, which are precursor to lignin or lignans. It is also a biosynthetic precursor to various stilbenoids and coumarins.

Surface-enhanced laser desorption/ionization (SELDI) is a soft ionization method in mass spectrometry (MS) used for the analysis of protein mixtures. It is a variation of matrix-assisted laser desorption/ionization (MALDI). In MALDI, the sample is mixed with a matrix material and applied to a metal plate before irradiation by a laser, whereas in SELDI, proteins of interest in a sample become bound to a surface before MS analysis. The sample surface is a key component in the purification, desorption, and ionization of the sample. SELDI is typically used with time-of-flight (TOF) mass spectrometers and is used to detect proteins in tissue samples, blood, urine, or other clinical samples, however, SELDI technology can potentially be used in any application by simply modifying the sample surface.

<span class="mw-page-title-main">Gentisic acid</span> Chemical compound

Gentisic acid is a dihydroxybenzoic acid. It is a derivative of benzoic acid and a minor (1%) product of the metabolic break down of aspirin, excreted by the kidneys.

α-Cyano-4-hydroxycinnamic acid Chemical compound

α-Cyano-4-hydroxycinnamic acid, also written as alpha-cyano-4-hydroxycinnamic acid and abbreviated CHCA or HCCA, is a cinnamic acid derivative and is a member of the phenylpropanoid family. The carboxylate form is α-cyano-4-hydroxycinnamate.

<span class="mw-page-title-main">3-Hydroxypicolinic acid</span> Chemical compound

3-Hydroxy picolinic acid is a picolinic acid derivative and is a member of the pyridine family. It is used as a matrix for nucleotides in MALDI mass spectrometry analyses.

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MALDI mass spectrometry imaging (MALDI-MSI) is the use of matrix-assisted laser desorption ionization as a mass spectrometry imaging technique in which the sample, often a thin tissue section, is moved in two dimensions while the mass spectrum is recorded. Advantages, like measuring the distribution of a large amount of analytes at one time without destroying the sample, make it a useful method in tissue-based study.

Sample preparation for mass spectrometry is used for the optimization of a sample for analysis in a mass spectrometer (MS). Each ionization method has certain factors that must be considered for that method to be successful, such as volume, concentration, sample phase, and composition of the analyte solution. Quite possibly the most important consideration in sample preparation is knowing what phase the sample must be in for analysis to be successful. In some cases the analyte itself must be purified before entering the ion source. In other situations, the matrix, or everything in the solution surrounding the analyte, is the most important factor to consider and adjust. Often, sample preparation itself for mass spectrometry can be avoided by coupling mass spectrometry to a chromatography method, or some other form of separation before entering the mass spectrometer. In some cases, the analyte itself must be adjusted so that analysis is possible, such as in protein mass spectrometry, where usually the protein of interest is cleaved into peptides before analysis, either by in-gel digestion or by proteolysis in solution.

<span class="mw-page-title-main">Matrix-assisted laser desorption electrospray ionization</span>

Matrix-assisted laser desorption electrospray ionization (MALDESI) was first introduced in 2006 as a novel ambient ionization technique which combines the benefits of electrospray ionization (ESI) and matrix-assisted laser desorption/ionization (MALDI). An infrared (IR) or ultraviolet (UV) laser can be utilized in MALDESI to resonantly excite an endogenous or exogenous matrix. The term 'matrix' refers to any molecule that is present in large excess and absorbs the energy of the laser, thus facilitating desorption of analyte molecules. The original MALDESI design was implemented using common organic matrices, similar to those used in MALDI, along with a UV laser. The current MALDESI source employs endogenous water or a thin layer of exogenously deposited ice as the energy-absorbing matrix where O-H symmetric and asymmetric stretching bonds are resonantly excited by a mid-IR laser.

<span class="mw-page-title-main">Sinapine</span> Chemical compound

Sinapine is an alkaloidal amine found in some seeds, particularly oil seeds of plants in the family Brassicaceae. It is the choline ester of sinapic acid.

The biosynthesis of phenylpropanoids involves a number of enzymes.

<span class="mw-page-title-main">Robert J. Cotter</span>

Robert J. Cotter was an American chemist and mass spectrometrist. His research contributed to many early advances in the field of time-of-flight mass spectrometry. From 1998 to 2000 he was president of the American Society for Mass Spectrometry. Cotter was also a co-investigator on the Mars Organic Molecule Analyzer (MOMA) project, developing a miniaturized, low power consumption ion trap/time-of-flight mass spectrometer that was to be deployed with the ExoMars rover, now the Rosalind Franklin rover.

<span class="mw-page-title-main">Canolol</span> Chemical compound

Canolol is a phenolic compound found in crude canola oil. It is produced by decarboxylation of sinapic acid during canola seed roasting.

<span class="mw-page-title-main">Desorption/ionization on silicon</span> Soft laser desorption method

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References

  1. Beavis RC, Chait BT (1989). "Matrix-assisted laser-desorption mass spectrometry using 355 nm radiation". Rapid Commun. Mass Spectrom. 3 (12): 436–9. Bibcode:1989RCMS....3..436B. doi:10.1002/rcm.1290031208. PMID   2520224.
  2. Beavis RC, Chait BT (1989). "Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins". Rapid Commun. Mass Spectrom. 3 (12): 432–5. Bibcode:1989RCMS....3..432B. doi:10.1002/rcm.1290031207. PMID   2520223.
  3. Bunzel M, Ralph J, Kim H, Lu F, Ralph SA, Marita JM, Hatfield RD, Steinhart H (2003). "Sinapate dehydrodimers and sinapate-ferulate heterodimers in cereal dietary fibre". J. Agric. Food Chem. 51 (5): 1427–1434. doi:10.1021/jf020910v. PMID   12590493.
  4. Tzagoloff A (1963). "Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline". Plant Physiology. 38 (2): 202–206. doi:10.1104/pp.38.2.202. PMC   549906 . PMID   16655775.
  5. 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
  6. Gávez MC, Barroso CG, Péez-Bustamante JA (1994). "Analysis of polyphenolic compounds of different vinegar samples". Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 199: 29–31. doi:10.1007/BF01192948. S2CID   91784893.
  7. 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