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Ortho-Vanillin

3-Methoxysalicylaldehyde eyes, and respiratory tract

ortho-Vanillin (2-hydroxy-3-methoxybenzaldehyde) is an organic solid present in the extracts and essential oils of many plants.{{cite journal

ortho-Vanillin is a fibrous, light-yellow, crystalline solid. Present in a variety of food products, it is not specifically sought after, and is therefore a less-commonly produced and encountered food additive.

History

ortho-Vanillin was first isolated, in 1876, by renowned German chemist Ferdinand Tiemann.{{cite journal

By 1920, the compound began to show use as a dye for hides.

Biological properties

ortho-Vanillin is harmful if ingested, irritating to eyes, skin and respiratory system, but has an unmistakable high of 1330 mg/kg in mice.

It is a weak inhibitor of tyrosinase, and displays both antimutagenic and comutagenic properties in Escherichia coli. However, its net effect makes it a “potent comutagen”.

ortho-Vanillin possesses moderate antifungal and antibacterial properties.

Uses

Today, most ortho-vanillin is used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals, for example, benafentrine and an antiandrogen compound called Pentomone.

Notes

References

  1. Noelting, Francis A. M.. (1910). "''o''-Hydroxy-''m''-methoxybenzaldehyde (Orthovanillin)". [[Annales de Chimie et de Physique]].
  2. Gerngross, Otto. (1920). "Dyeing hide with ''o''-vanillin and ''o''-protocatechualdehyde and aldehyde tanning". Angewandte Chemie.
  3. "Archived copy".
  4. (1999). "Tyrosinase inhibitory activity of the olive oil flavor compounds". Journal of Agricultural and Food Chemistry.
  5. (1989). "Enhancement and inhibition of mutation by ''o''-vanillin in ''Escherichia coli''". Mutation Research/DNA Repair.
  6. (1989). "A specific inhibition of induction of adaptive response by ''o''-vanillin, a potent comutagen". Biochemical and Biophysical Research Communications.
  7. (1975). "Antifungal and antibacterial effects of phenolic substances. A study of the relation between the biological activity and the constitution of the investigated compounds". Acta Universitatis Palackianae Olomucensis, Facultatis Medicae.
  8. (1986). "Synthesis of 5,6-dimethoxyquinazolin-2(1''H'')-ones". Journal of Heterocyclic Chemistry.
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This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

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