308358-04-5

Basic information

• Product Name: (R)-Pulegone Oxide
• Synonyms: (R)-Pulegone Oxide;(6R)-2,2,6-TriMethyl-1-oxaspiro[2.5]octan-4-one
• CAS NO: 308358-04-5
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• Product Categories: Heterocycles;Intermediates
• Mol File: 308358-04-5.mol

Chemical Properties

• Melting Point: 44 °C(Solv: hexane (110-54-3))
• Boiling Point: 245.1±23.0 °C(Predicted)
• Appearance: /
• Density: 1.04±0.1 g/cm3(Predicted)
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: (R)-Pulegone Oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Pulegone Oxide(308358-04-5)
• EPA Substance Registry System: (R)-Pulegone Oxide(308358-04-5)

Safety Data

• Hazardous Substances Data: 308358-04-5(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
(R)-Pulegone Oxide is used as a flavoring agent for its strong minty aroma, adding a refreshing and cooling sensation to various food and beverage products. It is particularly popular in the production of chewing gum, toothpaste, and mouthwashes.
(R)-Pulegone Oxide is also used as a fragrance ingredient in the perfumery industry, where it contributes to the creation of complex and long-lasting scents. Its minty aroma can be used to enhance the overall scent profile of perfumes, colognes, and other fragrance products.
Used in Pharmaceutical Industry:
(R)-Pulegone Oxide has potential applications in the pharmaceutical industry due to its chemical properties and structural characteristics. It can be used as an intermediate in the synthesis of various drugs and active pharmaceutical ingredients (APIs), particularly those with analgesic, anti-inflammatory, or antispasmodic properties.
Used in Cosmetics Industry:
In the cosmetics industry, (R)-Pulegone Oxide can be used as an additive in the formulation of personal care products, such as creams, lotions, and shampoos. Its minty aroma can provide a cooling and refreshing sensation when applied to the skin or scalp, making it an attractive ingredient for products aimed at providing a soothing and invigorating experience.
Used in Research and Development:
(R)-Pulegone Oxide can be utilized in research and development for the study of its chemical properties, structural characteristics, and potential applications in various fields. It can serve as a model compound for understanding the behavior of other monoterpenes and their derivatives, as well as for exploring new methods of synthesis and modification.

Upstream product

• 89-82-7 pulegone 

Downstream Products

• 230636-58-5 2-hydroxy-2-isopropyl-5-methylcyclohexanone 
• 3304-24-3 2-(1-hydroxy-1-methylethyl)-5-methylcyclohexanone 
• 119980-52-8 (R)-2-Hydroxy-2-(1-hydroxy-1-methyl-ethyl)-5-methyl-cyclohexanone 
• 101693-93-0 (5R)-5-methyl-2-(phenylthio)cyclohexan-1-one 
• 89-82-7 pulegone 
• 90528-94-2 (-)-(R)-5-methyl-2-allyl-2-cyclohexenone 
• 15228-74-7 (+)-fawcettimine 
• 915122-92-8 (R)-5-methyl-2-iodo-2-cyclohexen-1-one 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 10275-88-4 (+/-)-1,4,4-trimethyl-2-oxo-cyclopentanecarbaldehyde 
• 90461-82-8 Sodium; (R)-5-methyl-2-phenylsulfanyl-cyclohex-1-enolate 
• 34399-44-5 des-N-methyl-α-obscurine 

Relevant articles and documents

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An efficient synthesis of two Lycopodium alkaloids, (-)-carinatine A and (+)-lycopladine A, is achieved in eight steps. The synthesis features an intramolecular aldol reaction for assembling the 6,5-fused ring system, a subsequent Tsuji-Trost allylation for generating a quarternary carbon center, and a 6π-electrocyclization to form the pyridine ring.

Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids

Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-β-obscurine. Key steps in the syntheses include oxidative C-C bond cleavage of a piperidine ring in the core structure of the obscurine intermediate and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.

Efforts toward the synthesis of (+)-Lyconadin A

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A concise asymmetric total synthesis of (+)-fawcettimine

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The first asymmetric total synthesis of lycoposerramine-R

The first asymmetric total synthesis of lycoposerramine-R, a Lycopodium alkaloid possessing a novel skeleton, was accomplished by a strategy featuring the stereoselective intramolecular aldol cyclization giving a cis-fused 5/6 bicyclic skeleton and a new method for the construction of the pyridone ring via the aza-Wittig reaction.

Syntheses of (+)-complanadine A and lycodine derivatives by regioselective [2 + 2 + 2] cycloadditions

The dimeric alkaloid complanadine A has shown promise in regenerative science, promoting neuronal growth by inducing the secretion of growth factors from glial cells. Through the use of tandem, cobalt-mediated [2 + 2 + 2] cycloaddition reactions, two synthetic routes have been developed with different sequences for the formation of the unsymmetric bipyridyl core. The regioselective formation of each of the pyridines was achieved based on the inherent selectivity of the molecules or by reversing the regioselectivity through the addition of Lewis bases. This strategy has been successfully employed to provide laboratory access to complanadine A as well as structurally related compounds possessing the lycodine core.

A new approach to the bicyclo[3.3.1]nonane framework of huperzine A-like molecules via palladium-catalyzed intramolecular γ-arylation

In our synthetic studies toward huperzine A, a diastereoselective α′-alkylation of the α-amido-γ-methyl hexenone 4 was realized through a dianion intermediate which significantly enhanced the reactivity. Under the attempted Heck reaction conditions, an unexpected and unprecedented palladium-catalyzed intramolecular γ-arylation of 3 was observed, which generated 18 with bicyclo[3.3.1]nonane framework in satisfactory yield.

Total synthesis of (+)-fawcettidine

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