ortho-Vanillin

• 2 -hydroxy-3 -methoxybenzaldehyde
• O- vanillin
• 3- methoxysalicylaldehyde

Light yellow crystalline needles

Fixed

43-45 ° C

265-266 ° C

THF: 5.37 M, ethanol: 3.04 M, methanol: 2.27 M

Attention

1330 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Ortho- vanillin (2- hydroxy-3- methoxybenzaldehyde ) is an organic chemical compound with the molecular formula C8H8O3. It is a derivative of benzaldehyde having an additional hydroxyl and a methoxy group. The prefix ortho identifies here the position of the hydroxyl group with respect to the aldehyde group.

History and habitat

Ortho- vanillin was first discovered in 1876 by ​​Ferdinand Tiemann. It is present in extracts and essential oils of many plants. In 1910, Francis Nölting developed methods for the preparation of pure, also he could demonstrate the versatility of this compound as a synthetic precursor for a large number of compounds, such as coumarins. In 1920, the compound was used for the dyeing of animal skins. In foods, it is not in high demand and is therefore a less frequently produced and to be more appropriate additive.

Properties

Physical Properties

Ortho- vanillin has light yellow crystalline needles. It melts at 43-45 ° C and boils at 265-266 ° C. It is soluble in THF, ethanol and methanol. It crystallizes in the orthorhombic crystal system, space group P21 / a with lattice parameters a = 2509.9 pm, b = 2452.2 pm, c = 479.1 pm and 16 formula units per unit cell.

Chemical Properties

It differs significantly from its isomer, vanillin, because in contrast, it does not have the characteristic and intense scent of vanilla. The prefix ortho identifies here the position of the hydroxyl group with respect to the aldehyde group; vanillin in these two groups are in the para position.

Ortho- vanillin can be converted by fusion with potassium hydroxide in ortho- vanillin. This in turn may react with hydrogen bromide 2,3- dihydroxybenzoic acid.

Biological Properties

Ortho- vanillin is a weak inhibitor of tyrosinase, showing both antimutagenic and comutagene properties in Escherichia coli. It has a moderate anti-fungal and anti-bacterial properties.