Sinapinic acid

Last updated

Contents

Sinapinic acid
Sinapinic acid Sinapic acid.png
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
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 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 infludes many natural products. [1]

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). [2] For example, it can be found in wine, [3] vinegar, [4] and black plums. [5] Sinapine id found in black mustard seeds. It is considered a choline ester of sinapinic acid. [6]

Sinapic acid has attracted much interest as an antioxidant [7]

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. [8]

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. [9]

Research

Sinapic acid is a used in MALDI mass spectrometry. [10] 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.