Eudesmic acid

Eudesmic acid is an O-methylated trihydroxybenzoic acid.

Eudesmic acid
Chemical structure of eudesmic acid
Names
Preferred IUPAC name
3,4,5-Trimethoxybenzoic acid
Other names
Gallic acid trimethyl ether
Tri-O-methylgallic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.863
UNII
  • InChI=1S/C10H12O5/c1-13-7-4-6(10(11)12)5-8(14-2)9(7)15-3/h4-5H,1-3H3,(H,11,12) ☒N
    Key: SJSOFNCYXJUNBT-UHFFFAOYSA-N ☒N
  • InChI=1/C10H12O5/c1-13-7-4-6(10(11)12)5-8(14-2)9(7)15-3/h4-5H,1-3H3,(H,11,12)
    Key: SJSOFNCYXJUNBT-UHFFFAOYAD
  • COC1=CC(=CC(=C1OC)OC)C(=O)O
Properties
C10H12O5
Molar mass 212.201 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Natural Occurrence

It can be found in Eucalyptus spp.[1]

Synthesis

Eudesmic acid is most directly synthesized by reaction of gallic acid with dimethyl sulfate.[2]

Derivatives
  1. Esterified with Deanol.[3]
  2. Trimebutine
  3. Amoproxan
  4. Bernzamide
  5. 3,4,5-trimethoxy-N-(pyridin-4-yl)benzamide [31638-97-8].[4]
  6. Butobendine
  7. Capobenic acid
  8. Dilazep
  9. Ecipramidil
  10. Fepromide
  11. Hexobendine
  12. Mepramidil (Diphenamilate)
  13. TMB-8 [57818-92-5]
  14. Tricetamide (Trimeglamide)
  15. Trimethobenzamide
  16. Trimetozine
  17. Tritiozine (ala trimetozine but thioamide).
  18. Trocimine [14368-24-2]
  19. Troxipide (Lefron)
  20. Troxonium
  21. Troxypyrrolium (Troxypyrrole, Trox)
  22. Trimetamide.
  23. Vinmegallate (RGH-4417)
  24. Leonuramine and Leonurine.
  25. Methoserpidine, Reserpine and Deserpidine.

References
  1. HPLC analysis of flavonoids and phenolic acids and aldehydes in Eucalyptus spp. E. Conde, E. Cadahía and M. C. Garcia-Vallejo, Chromatographia, Volume 41, Numbers 11-12, 657-660, doi:10.1007/BF02267800
  2. Ikan, Raphael (1991). Natural Products: A Laboratory Guide 2nd Ed. San Diego: Academic Press, Inc. pp. 232–235. ISBN 0123705517.
  3. Ex25 in GB 879259, "Acid addition salts of 2-dimethylaminoethanol and central nervous system stimulant compositions containing them", published 1961-10-11, assigned to Riker Laboratories Inc.
  4. ES 456989, Sanjosé, Miguel Izquierdo & Ulpiano Martín-Escudero, Pérez, "Procedimiento de obtencion de un derivado de 4-aminopiridina y sus sales [Procedure for obtaining a 4-aminopyridine derivative and its salts]", published 1978-07-16, assigned to Laboratorio Farmaceutico Quimico-Lafarquim SA
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