Sotolon

• 3-hydroxy- 4 ,5- dimethylfuran -2 (5H )-one ( IUPAC)
• 2-hydroxy -3-methyl -2 -penten- 4 -olide

1.049 g · cm -3

26-29 ° C

184 ° C

Template: Infobox chemical / molecular formula search available

Sotolon is a heterocyclic compound having the structure of an intramolecular carboxylic acid, ester ( lactone ). The liquid at room temperature the substance is a strong flavoring which in low concentration by maple syrup, caramel or burnt sugar, a high concentration of curry, lovage ( Levisticum officinale) or fenugreek (Trigonella foenum -graecum ) smells.

Material properties

Sotolon is a white to pale yellow solid or a colorless to slightly yellow liquid. The odor perception threshold of the substance is below a few micrograms / kg.

Occurrence

Sotolon is the principal odor component in the two plants lovage and fenugreek and has a significant share of the flavors of maple syrup. In roasted Virginian tobacco, matured in Madeira wines and decades-old Port wines, Sake and other rice wines sotolon is included and has a share in flavor. Also in citrus soft drinks sotolon has been found, but there is an off-flavor, which is formed non-enzymatically during storage of ethanol and ascorbic acid.

Biological Significance

The consumption of large quantities of sotolonhaltigen food and plants like fenugreek can lead to take the urine and sweat temporarily the smell of maple syrup, as sotolon is secreted relatively unchanged from the body. People suffering from the autosomal recessive Maple syrup urine disease, having only defective 2- keto - dehydrogenase complexes ( BCKAD complex), which leads to an impaired degradation of the amino acids leucine ( Leu), isoleucine (Ile ) and valine (Val). These accumulate in the blood, as well as sotolon derived from the leucine intermediary metabolism and is detectable in the smells of maple syrup urine of the patient.

Others

On the night of June 11, 2013 four kilograms sotolon were released in a chemical plant of the company Silesia in Neuss- All Saints on a 120 m high chimney. As part of a distillation process, it came to the exit of the flavor sotolon. By contact of the substance with a hot surface, it then came to an evaporation. This led to a pronounced smell of soup or " Maggi " was perceived in the morning in the Cologne and later in Dusseldorf from residents. The town fire department continued to cause study measuring six vehicles and two Messleitwagen one.