Description
Methylcyclopentenolone has a sweet flavor somewhat similar to
licorice.
Chemical Properties
Methylcyclopentenolone has a sweet flavor somewhat similar to licorice. This compound is also reported to have a nutty
odor, and a maple-licorice aroma in dilute solution
Chemical Properties
WHITE TO OFF-WHITE POWDER
Occurrence
Reported formed during the dry distillation of wood; found also in the corresponding tar oil; identified in fenugreek. Also reported found in black currants, onion, wheat bread, cured and cooked pork, beer, cocoa, coffee, barley, filbert, almond,
sukiyaki, licorice, dried bonito and roasted chicory root
Definition
ChEBI: 3-Methyl-1,2-cyclopentanedione is a cyclic ketone.
Preparation
Sublimes and distills at atmospheric pressure with decomposition.
Aroma threshold values
Detection: 300 ppb
Taste threshold values
Taste characteristics at 5 ppm: sweet, maple, bready, caramellic with nutty nuances.
General Description
3-Methyl-1,2-cyclopentanedione is present in coffee and is capable of scavenging peroxynitrite. It also has anti-inflammatory effects.
Synthesis
1-Hydroxy-2,5-hexanedione (130 mg) was used as starting material and dissolved in water at 80 °C. Sodium bicarbonate (8.4 mg) was added as a catalyst and the reaction lasted for 12 hours. Upon completion of the reaction, extraction was carried out using chloroform to isolate the product. Purification by silica gel column chromatography afforded 3-methylcyclopentane-1,2-dione (91 mg) in 81% yield. The final product was analyzed by GC-MS and confirmed by comparison with 3-methylcyclopentane-1,2-dione standard.
References
[1] Patent: CN108129278, 2018, A. Location in patent: Paragraph 0018-0025
