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Sinapinic acid information


Sinapinic acid
Sinapinic acid
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
CAS Number
  • 530-59-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15714 checkY
ChEMBL
  • ChEMBL109341 checkY
ChemSpider
  • 553361 checkY
DrugBank
  • DB08587 checkY
PubChem CID
  • 637775
UNII
  • 68A28V6010 checkY
CompTox Dashboard (EPA)
  • DTXSID201355800 DTXSID40862129, DTXSID201355800 Edit this at Wikidata
InChI
  • 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
SMILES
  • COc1cc(cc(c1O)OC)/C=C/C(=O)O
Properties
Chemical formula
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).
checkY verify (what is checkY☒N ?)
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 sinapinic acid.[4]

  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.

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