Formula C8H8O3 Appearance Yellow, fibrous solid | Molar mass 152.15 g/mol | |
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ortho-Vanillin (2-Hydroxy-3-methoxybenzaldehyde) is an organic solid present in the extracts and essential oils of many plants. Its functional groups include aldehyde, ether and phenol. ortho-Vanillin, a compound of the formula C8H8O3, is distinctly different from its more prevalent isomer, vanillin. The "ortho-" prefix refers to the position of the compound’s hydroxyl moiety, which is found in the para-position in vanillin.
Contents
ortho-Vanillin is a fibrous, light-yellow, crystalline solid. Unlike its better-known analogue, o-vanillin does not have the characteristic and intense odor of vanilla. 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. 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.
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 LD50 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.