Ortho-vanillin
Encyclopedia
ortho-Vanillin 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 the to 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
. 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
.
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 coumarin
s.
By 1920, the compound began to show use as a dye
for hides.
It is a weak inhibitor
of tyrosinase
, and displays both antimutagenic
and comutagen
ic properties in Escherichia coli
. However, its net effect makes it a “potent comutagen.”
ortho-Vanillin possesses moderate antifungal
and antibacterial
properties.
and as a synthetic precursor for pharmaceuticals.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
solid present in the extracts and essential oils of many plants. Its functional groups include aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
, ether
Ether
Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...
and phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
. ortho-Vanillin, a compound of the formula C8H8O3, is distinctly different from its more prevalent isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
, vanillin
Vanillin
Vanillin is a phenolic aldehyde, an organic compound with the molecular formula C8H8O3. Its functional groups include aldehyde, ether, and phenol. It is the primary component of the extract of the vanilla bean. It is also found in Leptotes bicolor, roasted coffee and the Chinese red pine...
. The "ortho
Arene substitution patterns
Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon.- Ortho, meta, and para substitution :...
-" prefix refers the to position of the compound’s hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
moiety, which is found in the para
Arene substitution patterns
Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon.- Ortho, meta, and para substitution :...
-position in vanillin.
ortho-Vanillin is a fibrous, light-yellow, crystalline solid
Solid
Solid is one of the three classical states of matter . It is characterized by structural rigidity and resistance to changes of shape or volume. Unlike a liquid, a solid object does not flow to take on the shape of its container, nor does it expand to fill the entire volume available to it like a...
. Unlike its better-known analogue, o-vanillin does not have the characteristic and intense odor of vanilla
Vanilla
Vanilla is a flavoring derived from orchids of the genus Vanilla, primarily from the Mexican species, Flat-leaved Vanilla . The word vanilla derives from the Spanish word "", little pod...
. Present in a variety of food products, it is not specifically sought after, and is therefore a less-commonly produced and encountered food additive
Food additive
Food additives are substances added to food to preserve flavor or enhance its taste and appearance.Some additives have been used for centuries; for example, preserving food by pickling , salting, as with bacon, preserving sweets or using sulfur dioxide as in some wines...
.
History
ortho-Vanillin was first isolated, in 1876, by renowned GermanGermany
Germany , officially the Federal Republic of Germany , is a federal parliamentary republic in Europe. The country consists of 16 states while the capital and largest city is Berlin. Germany covers an area of 357,021 km2 and has a largely temperate seasonal climate...
chemist
Chemist
A chemist is a scientist trained in the study of chemistry. Chemists study the composition of matter and its properties such as density and acidity. Chemists carefully describe the properties they study in terms of quantities, with detail on the level of molecules and their component atoms...
Ferdinand Tiemann
Ferdinand Tiemann
Johann Karl Wilhelm Ferdinand Tiemann was a German chemist and together with Reimer discoverer of the Reimer-Tiemann reaction.Beginning in 1866, Tiemann studied pharmacy at the TU Braunschweig where he graduated in 1869...
. 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 coumarin
Coumarin
Coumarin is a fragrant chemical compound in the benzopyrone chemical class, found in many plants, notably in high concentration in the tonka bean , vanilla grass , sweet woodruff , mullein , sweet grass , cassia cinnamon and sweet clover...
s.
By 1920, the compound began to show use as a dye
Dye
A dye is a colored substance that has an affinity to the substrate to which it is being applied. The dye is generally applied in an aqueous solution, and requires a mordant to improve the fastness of the dye on the fiber....
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
Enzyme inhibitor
An enzyme inhibitor is a molecule that binds to enzymes and decreases their activity. Since blocking an enzyme's activity can kill a pathogen or correct a metabolic imbalance, many drugs are enzyme inhibitors. They are also used as herbicides and pesticides...
of tyrosinase
Tyrosinase
Tyrosinase also known as monophenol monooxygenase is an enzyme that catalyses the oxidation of phenols and is widespread in plants and animals...
, and displays both antimutagenic
Mutation
In molecular biology and genetics, mutations are changes in a genomic sequence: the DNA sequence of a cell's genome or the DNA or RNA sequence of a virus. They can be defined as sudden and spontaneous changes in the cell. Mutations are caused by radiation, viruses, transposons and mutagenic...
and comutagen
Comutagen
A comutagen is a substance that is not a mutagen by itself, but in the presence of a mutagen, enhances mutagenic activity....
ic properties in Escherichia coli
Escherichia coli
Escherichia coli is a Gram-negative, rod-shaped bacterium that is commonly found in the lower intestine of warm-blooded organisms . Most E. coli strains are harmless, but some serotypes can cause serious food poisoning in humans, and are occasionally responsible for product recalls...
. However, its net effect makes it a “potent comutagen.”
ortho-Vanillin possesses moderate antifungal
Fungus
A fungus is a member of a large group of eukaryotic organisms that includes microorganisms such as yeasts and molds , as well as the more familiar mushrooms. These organisms are classified as a kingdom, Fungi, which is separate from plants, animals, and bacteria...
and antibacterial
Bacteria
Bacteria are a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals...
properties.
Uses
Today, most ortho-vanillin is used in the study of mutagenesisMutagenesis
Mutagenesis is a process by which the genetic information of an organism is changed in a stable manner, resulting in a mutation. It may occur spontaneously in nature, or as a result of exposure to mutagens. It can also be achieved experimentally using laboratory procedures...
and as a synthetic precursor for pharmaceuticals.