105252-84-4

Usage

Uses

Used in Flavor and Fragrance Industry:
Dihydrocarvone is utilized as a flavoring agent in food and beverages, adding a refreshing minty taste to various products. In the perfumery and personal care sector, it serves as a fragrance, enhancing the scent profiles of numerous products with its distinctive carvone-like aroma.
Used in Pharmaceutical Industry:
(-)-(6S)-4,10-DIMETHYL-7-ISOPROPYL-1,5-DIOXASPIRO[5.5] UNDEC-3-EN-2-ON has potential applications in the pharmaceutical industry, where it has been studied for its therapeutic effects. Dihydrocarvone has shown promise as an analgesic, providing pain relief, and as an agent that can inhibit the growth of cancer cells, offering a natural alternative to synthetic treatments.
Used in Agricultural Industry:
Dihydrocarvone has been investigated for its potential as a natural alternative to synthetic pesticides. It has demonstrated antibacterial, antifungal, and insecticidal properties, making it a valuable component in the development of eco-friendly and sustainable pest control solutions for agriculture.

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 10458-14-7 (2R,5S)-menthone 
• 126797-63-5 (6S,7S,10R)-4-Bromomethyl-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-3-en-2-one 
• 105252-83-3 7-isopropyl-10-methyl-1,5-dioxaspiro[5.5]undecane-2,4-dione 
• 75-36-5 acetyl chloride 
• 1694-31-1 tert-butyl acetoacetate 

Downstream Products

• 10458-14-7 (2R,5S)-menthone 
• 6168-83-8 (S)-3-Hydroxybutanoic Acid 

Relevant academic research and scientific papers

(6S,7S,10R)- and (6R,7S,10R)-Isopropyl-10-methyl-4-oxo-1,5-dioxaspiroundec-2-enes having an Electron-withdrawing Substituent at the 2-Position: Synthesis and Use in Asymmetric Diels-Alder Reactions

Chiral spirocyclic dioxinones (S)-(6) and (S)-(7) have been synthesized from (-)-menthone and used in Diels-Alder reactions with cyclopentadiene; remarkable diastereofacial selectivity (isopropyl side) and endo preference observed in these reactions have offered a new methodology for asymmetric Diels-Alder reactions.

Cycloadditions, 53. New Spirocyclic Chiral Dienes - Synthesis and Diastereoselective Diels-Alder Reactions with N-Phenylmaleimide

Synthesis and diastereoselective Diels-Alder reactions of new spirocyclic chiral dienes are reported.Starting with diketene and (-)-menthone (1), we prepared the diastereomeric diketene-menthone adducts 2 and 3.Further derivatization and olefination afforded four chiral dienes 12-15.Diastereoselective Diels-Alder reactions of these dienes with N-phenylmaleimide (NPM) under high-pressure conditions yielded the corresponding cycloadducts 16-19.Olefination of 6-diethylphosphonomethyl-2,2-dimethyl-1,3-dioxin-4-one 8 with formaldehyde led to unexpected compounds 9-11 resulting from the originally formed olefination product. - Key Words: Dienes, chiral / 1,3-Dioxin-4-ones / (-)-Menthone / Diels-Alder reactions, diastereoselective / Cycloadditions, high-pressure

Note on Mono- and Bisadducts of Diketene to (-)-Menthone

Onium salt and acid catalyzed addition of diketene to (-)-menthone gives improved yields of 2 and 3.Excess of diketene leads to diastereomeric mixtures of compounds 4 and 6 from menthone and menthol, respectively. - Key words: 1,3-Dioxin-4-ones from Ketones