Ortho-Vanillin Explained

ortho-Vanillin (2-hydroxy-3-methoxybenzaldehyde) is an organic solid present in the extracts and essential oils of many plants.^{[1] [2] [3]} Its functional groups include aldehyde, ether and phenol. ortho-Vanillin, a compound of the formula C₈H₈O₃, is distinctly different from its more prevalent isomer, meta-vanillin. The "ortho-" prefix refers to the position of the compound’s hydroxyl moiety, which is found in the para-position in vanillin.

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.^[4] By 1910, methods for its purification had been developed by Francis Noelting, who similarly demonstrated its versatility as a general synthetic precursor for a diverse array of compounds, such as the coumarins.^[5]

By 1920, the compound began to show use as a dye for hides.^[6]

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.^[7]

It is a weak inhibitor of tyrosinase,^[8] and displays both antimutagenic and comutagenic properties in Escherichia coli.^[9] However, its net effect makes it a “potent comutagen”.^[10]

ortho-Vanillin possesses moderate antifungal and antibacterial properties.^[11]

Uses

Today, most ortho-vanillin is used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals, for example, benafentrine^[12] and an antiandrogen compound called Pentomone.

See also

• Vanillin
• 2-Hydroxy-5-methoxybenzaldehyde
• Isovanillin
• 2-Hydroxy-4-methoxybenzaldehyde

Notes and References

1. Abou Zeid, A. H. . Sleem, A. A. . Natural and stress constituents from Spinacia oleracea L. leaves and their biological activities. Bulletin of the Faculty of Pharmacy (Cairo University). 2002. 40. 2. 153–167.
2. Barbe, Jean-Christophe . Bertrand, Alain. . Quantitative analysis of volatile compounds stemming from oak wood. Application to the aging of wines in barrels. Journal des Sciences et Techniques de la Tonnellerie. 1996. 2. 77–88.
3. Brunke, E. J. . Hammerschmidt, F. J. . Schmaus, G. . Das etherische Öl von Santolina chamaecyparissus L. . The essential oil of Santolina chamaecyparissus L.. Parfümerie und Kosmetik. 1992. 73. 9. 617–637.
4. Tiemann, Ferdinand . Ueber die der Coniferyl- und Vanillinreihe angehörigen Verbindungen . On coniferyl and vanillin series-related compounds . . 1876. 9 . 409–423. 10.1002/cber.187600901133.
5. Noelting, Francis A. M. . o-Hydroxy-m-methoxybenzaldehyde (Orthovanillin) . . 1910 . 19 . 476–550.
6. Gerngross, Otto . Dyeing hide with o-vanillin and o-protocatechualdehyde and aldehyde tanning . Angewandte Chemie . 1920 . 33 . 44 . 136–138. 10.1002/ange.19200334403 .
7. http://msds.chem.ox.ac.uk/VA/o-vanillin.html
8. Kubo, Isao . Kinst-Hori, Ikuyo . Tyrosinase inhibitory activity of the olive oil flavor compounds . Journal of Agricultural and Food Chemistry . 1999 . 47 . 11 . 4574–4578 . 10.1021/jf990165v . 10552852 .
9. Watanabe, Kazuko . Ohta, Toshihiro . Shirasu, Yasuhiko . Enhancement and inhibition of mutation by o-vanillin in Escherichia coli . Mutation Research/DNA Repair . 1989 . 218 . 2 . 105–9 . 10.1016/0921-8777(89)90016-5 . 2671704 .
10. Takahashi, Kazuhiko . Sekiguchi, Mutsuo . Kawazoe, Yutaka . A specific inhibition of induction of adaptive response by o-vanillin, a potent comutagen . Biochemical and Biophysical Research Communications . 1989 . 162 . 3 . 1376–81 . 10.1016/0006-291X(89)90826-7 . 2669748 .
11. Leifertova, I. . Hejtmankova, N. . Hlava, H. . Kudrnacova, J. . Santavy, F. . 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 . 1975 . 74 . 83–101.
12. Press. Jeffery B.. Bandurco. Victor T.. Wong. Elizabeth M.. Hajos. Zoltan G.. Kanojia. Ramesh M.. Mallory. Robert A.. Deegan. Edward G.. Mcnally. James J.. Roberts. Jerry R.. Cotter. Mary Lou. Graden. David W.. Lloyd. John R.. Synthesis of 5,6-dimethoxyquinazolin-2(1H)-ones. Journal of Heterocyclic Chemistry. 23. 6. 1986. 1821–1828. 0022-152X. 10.1002/jhet.5570230643.