22954-83-2

Usage

Uses

Used in Food and Beverage Industry:
3,6-Dihydro-4,6,6-trimethyl-2H-pyran-2-one is used as a flavoring agent for its sweet, caramel-like taste, enhancing the flavor profiles of various food and beverage products.
Used in Perfume and Fragrance Industry:
In the perfume and fragrance industry, 3,6-Dihydro-4,6,6-trimethyl-2H-pyran-2-one is utilized as a component to add a fruity and sweet note to scents, contributing to the overall aroma and appeal of perfumes and fragrances.
Used in Health and Wellness Research:
3,6-Dihydro-4,6,6-trimethyl-2H-pyran-2-one is studied for its potential health effects, including antioxidant and anti-cancer properties. While research is ongoing, it holds promise for future applications in health and wellness products.

InChI:InChI=1/C8H12O2/c1-6-4-7(9)10-8(2,3)5-6/h5H,4H2,1-3H3

Upstream product

• 463-51-4 Ketene 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 64-19-7 acetic acid 
• 3102-33-8 trans-3-penten-2-one 
• 97309-50-7 5-Chlor-4,6,6-trimethyl-5,6-dihydro-2H-pyran-2-on 
• 4478-63-1 3,4-epoxy-4-methyl-2-pentanone 
• 97309-18-7 (Z)-4,5-Epoxy-3,5-dimethyl-2-hexensaeure-ethylester 
• 97309-16-5 (Z)-4,5-Epoxy-3,5-dimethyl-2-hexensaeure-methylester 
• 97309-39-2 4,6,6-Trimethyl-5-trimethylsiloxy-5,6-dihydro-2H-pyran-2-on 
• 97332-46-2 5-Hydroxy-4,6,6-trimethyl-5,6-dihydro-2H-pyran-2-on 
• 97309-48-3 3-Chlor-4,6,6-trimethyl-3,6-dihydro-2H-pyran-2-on 

Downstream Products

• 20628-36-8 4,6,6-Trimethyl-3,4,5,6-tetrahydro-2H-pyran-2-on 

Relevant academic research and scientific papers

Trienediolates of hexadienoic acids in synthesis. Addition to unsaturated ketones. A convergent approach to the synthesis of retinoic acids

The regioselectivity of the addition of the lithium trienediolates generated from hexa-2,4-dienoic acids 1 and 2 or the dihydropyran-2-ones 4 and 5 to unsaturated ketones 6 is studied. Equilibration conditions favour reaction of the trienediolates through their ω carbon, and the ketones according to 1,2- and 1,4-additions. β-Ionone 6a and the aryl-butenone 6b lead to the 1,2-ω-adducts 8, which undergo a facile acid catalyzed dehydration to retinoic acids 11. On reaction with the unsaturated ketone 6b or with the aryl ketones 21, the trimethyldihydropyran-2-one 5 leads to γ'-adducts derived from deprotonation of the chain methyl substituent along with the 1,4-ω-adducts.

Trienediolates of hexadienoic acids in synthesis, synthesis of retinoic and nor-retinoic acids

Double deprotonation of either (E,E)-3-methyl-2,4-hexadienoic acid 2, or 4,6-dimethyldihydro-2-pyrone 3 generates apparently the same lithium trienediolate, which affords ω-hydroxy acids 9 on reaction with ketones 7. Hydroxy acids 9 are easily dehydrated to octatrienoic acids 5, which are structurally related to retinoic acid. Similarly, sorbic acid 1 leads to nor-retinoic acid analogs 6.

Formation and Reactivity of Hydroxy-substituted γ- and δ-Lactones

Hydrolysis of the esters (Z)-6-8 with H2SO4 in acetone leads to a mixture of γ- (17-19) and δ-Lactones (13-15) in various ratios.From (Z)-9 the rearrangement product 20 is obtained.By reaction of (Z)-6-9 with Et2O-BF3 the δ-lactones 13-16 are formed only.The saturated esters 10-12 hydrolyze to give a γ/δ-lactone mixture 24-26/21-23.Changing to BF3, favors the rearrangement 10 -> 30. - The δ-lactones 13-16 are not dehydrated with POCl3 in pyridine but chlorinated to afford 31-34.On heating in pyridine 33 and 34 are dehydrochlorinated to give the α-pyrones 38 and 39.Dechlorination with zinc in acetic acid leads to β,γ-unsaturated δ-lactones (31,35 -> 44; 32 -> 45; 33 -> 46).The mixture of saturated γ/δ-lactones 21b/24a/24b yields with POCl3 the elimination products 50 and 51, while a 23/26a/26b mixture furnishes the unsaturated γ-lactones 53a, b, and 54 as well as the chlorinated δ-lactones 55.Hydrogenation (44 -> 56; 45 -> 57; 46 -> 58; 51-> 59; 53/54 -> 60) gives the saturated parent compounds.