Sinapinic acid

Sinapinic acid
Identifiers
CAS number 530-59-6 Y
PubChem 637775
ChemSpider 553361 Y
DrugBank DB08587
ChEBI CHEBI:15714 Y
ChEMBL CHEMBL109341 Y
Jmol-3D images Image 1
Properties
Molecular formula C11H12O5
Molar mass 224.21 g/mol
Exact mass 224.068473 u
Melting point

203–205 °C (decomposes)

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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

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 sinapic acid.[4]

See also

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. 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. 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. ^ Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline. Alexander Tzagoloff, Plant Physiol. 1963 March; 38(2), pp. 202–206, PMC PMC549906