Sinapinic acid: Difference between revisions

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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]].<ref name="Bunzel 2003">{{cite journal |author=Bunzel M, Ralph J, Kim H, Lu F, Ralph SA, Marita JM, Hatfield RD, Steinhart H |title=Sinapate dehydrodimers and sinapate-ferulate heterodimers in cereal dietary fibre |journal=J. Agric. Food Chem. |volume=51 |pages=1427–1434 |year=2003 |doi=10.1021/jf020910v |pmid=12590493 |issue=5}}</ref>
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]].<ref name="Bunzel 2003">{{cite journal |author=Bunzel M, Ralph J, Kim H, Lu F, Ralph SA, Marita JM, Hatfield RD, Steinhart H |title=Sinapate dehydrodimers and sinapate-ferulate heterodimers in cereal dietary fibre |journal=J. Agric. Food Chem. |volume=51 |pages=1427–1434 |year=2003 |doi=10.1021/jf020910v |pmid=12590493 |issue=5}}</ref>


[[Sinapine]] is an alkaloidal amine found in black mustard seeds. It is considered a [[choline]] ester of [[sinapic acid]].<ref>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, {{PMCID|549906}}</ref>
[[Sinapine]] is an alkaloidal amine found in black mustard seeds. It is considered a [[choline]] ester of [[sinapic acid]].<ref>{{cite pmid|16655775}}</ref>


== Natural occurrences ==
== Natural occurrences ==
Sinapinic acid can be found in [[vinegar]].<ref>Analysis of polyphenolic compounds of different vinegar samples. Miguel Carrero Gálvez, Carmelo García Barroso and Juan Antonio Pérez-Bustamante, Zeitschrift für Lebensmitteluntersuhung und -Forschung A, Volume 199, Number 1, pages 29-31, {{doi|10.1007/BF01192948}}</ref>
Sinapinic acid can be found in [[vinegar]].<ref>{{cite doi|10.1007/BF01192948}}</ref>


== See also ==
== See also ==

Revision as of 22:50, 15 April 2012

Sinapinic acid
Sinapinic acid
Names
IUPAC name
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
  • 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+ checkY
    Key: PCMORTLOPMLEFB-ONEGZZNKSA-N checkY
  • 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 203–205 °C (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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]

Natural occurrences

Sinapinic acid can be found in vinegar.[5]

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 16655775, please use {{cite journal}} with |pmid=16655775 instead.
  5. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1007/BF01192948, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1007/BF01192948 instead.
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