3188-00-9 Usage
Description
2-Methyltetrahydrofuran-3-one is an organic compound with a bread and buttery topnote and an odor reminiscent of wintergreen. It is a colorless to light yellow liquid that can be prepared by hydrolytic decarboxylation of 2-methyl-4-carbomethoxytetrahydrofuran-3-one or by acid-catalyzed ring closure of p-alkoxy-diazoketones.
Uses
Used in Flavor and Fragrance Industry:
2-Methyltetrahydrofuran-3-one is used as a flavoring agent for its nutty and astringent taste with a slight creamy, almond nuance. It is found as a constituent in various food items such as coffee aroma, roasted filbert nuts, guava, raisin, pineapple, onion, baked and fried potato, tomato, wheat bread, crispbread, smoked fish, cooked beef and pork, pork liver, rum, cocoa, peanuts, potato chips, passion fruit, beans, mushroom, tamarind, sweet potato, licorice, malt, dried bonito, cherimoya, okra, and maté.
Used in Quorum Sensing Inhibition:
2-Methyltetrahydrofuran-3-one is used as a quorum sensing inhibitor-molecule to investigate its effect on growth and biofilm formation in Hafnia alvei, which is a bacterium that can cause infections in humans and animals.
Preparation
By hydrolytic decarboxylation of 2-methyl-4-carbomethoxytetrahydrofuran-3-one; by acid-catalyzed ring closure of
β-alkoxy-diazoketones
Check Digit Verification of cas no
The CAS Registry Mumber 3188-00-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,8 and 8 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 3188-00:
(6*3)+(5*1)+(4*8)+(3*8)+(2*0)+(1*0)=79
79 % 10 = 9
So 3188-00-9 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3/t4-/m0/s1
3188-00-9Relevant articles and documents
A short and efficient synthesis of 2-methyltetrahydrofuran-3-one
Ragoussis, Valentine,Lagouvardos, Dimitrios J.,Ragoussis, Nikitas
, p. 4273 - 4278 (1998)
2-Methyltetrahydrofuran-3-one (3), a volatile constituent of the aroma complex of roasted coffee, is efficiently prepared in satisfactory yield (55,2%) by oxidative hydroxylation of the 2-acetylbutyrolactone (4).
Thermal decomposition of ascorbic acid
Vernin, Gaston,Chakib, Soundouss,Rogacheva, Sonia M.,Obretenov, Tzvetan D.,Parkanyi, Cyril
, p. 1 - 15 (2007/10/03)
Thermal degradation of L-ascorbic acid at 300 °C in the absence of a solvent yielded mostly furan derivatives and α,β-unsaturated cyclic ketones with a five-membered ring. Some of the furan derivatives are the same as those obtained in the Maillard reaction, with the reductones undergoing retroaldol reaction, decarboxylation, oxidation, and hydrolysis. In propylene glycol, under milder conditions (180 °C), the carbonyl and dicarbonyl derivatives resulting from the decomposition react with the solvent and give cyclic acetals and ketals (1,3-dioxolanes). The products were identified by GC-MS using the SPECMA data bank.
A CONDENSED SYNTHESIS OF DIHYDRO-3(2H)-FURANONE
Tarnchompoo, Bonkoch,Thebtaranonth, Yodhathai
, p. 5567 - 5570 (2007/10/02)
A straight forward synthesis of dihydro-3(2H)-furanone is described.An attempted preparation of the oxetan-3-one precursor 10 by this method gave, instead, the ring enlargement product 11.
