Sinapinic acid

Sinapinic acid
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
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+ 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 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 checkYX markN ?)

Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.) is an organic compound with the formula (CH3O)2(HO)C6H2CH=CHCO2H. It is naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family, which includes many natural products.

Natural occurrences

Sinapic acid is found widely in plants including those used for human nutrition. Some common sinapic acid conjugates include esters with malate and choline (sinapine). For example, it can be found in wine, vinegar, and black plums. Sinapine is found in black mustard seeds. It is considered a choline ester of sinapinic acid.

Sinapic acid has attracted much interest as an antioxidant

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.

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.

Research

Sinapic acid is a used in MALDI mass spectrometry. 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.

See also

References

  1. ↑ Clifford MN (1999). "Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden". Journal of the Science of Food and Agriculture. 79 (3): 362–372. Bibcode:1999JSFA...79..362C. doi:10.1002/(sici)1097-0010(19990301)79:3<362::aid-jsfa256>3.0.co;2-d.
  2. ↑ Nićiforović N, Abramovič H (2014). "Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity". Comprehensive Reviews in Food Science and Food Safety. 13 (1): 34–51. doi:10.1111/1541-4337.12041. PMID 33412688.
  3. ↑ 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
  4. ↑ 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.
  5. ↑ Jawad M, Ali M, Qasim S, Akbar A, Khan NA, Sadiq MB (2022-08-02). "Determination of Phenolic Compounds and Bioactive Potential of Plum (Prunus salicina) Peel Extract Obtained by Ultrasound-Assisted Extraction". BioMed Research International. 2022 7787958. doi:10.1155/2022/7787958. ISSN 2314-6133. PMC 9433295. PMID 36060132.
  6. ↑ 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.
  7. ↑ Humphreys JM, Chapple C (2002). "Rewriting the lignin roadmap". Current Opinion in Plant Biology. 5 (3): 224–229. Bibcode:2002COPB....5..224H. doi:10.1016/s1369-5266(02)00257-1. PMID 11960740.
  8. ↑ 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.
  9. ↑ 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
  10. ↑ 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.