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(R)-Pulegone Oxide, also known as the oxidized form of the monoterpene Pulegone, is a white solid compound that is commonly found in fragrant and flavoring agents. It is derived from Pulegone, which is a naturally occurring monoterpene that possesses a strong minty aroma and is widely used in the flavor and fragrance industry.

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  • 308358-04-5 Structure
  • Basic information

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

    1. Melting Point: 44 °C(Solv: hexane (110-54-3))
    2. Boiling Point: 245.1±23.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.04±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: Chloroform, Dichloromethane, Ethyl Acetate
    9. CAS DataBase Reference: (R)-Pulegone Oxide(CAS DataBase Reference)
    10. NIST Chemistry Reference: (R)-Pulegone Oxide(308358-04-5)
    11. EPA Substance Registry System: (R)-Pulegone Oxide(308358-04-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 308358-04-5(Hazardous Substances Data)

308358-04-5 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.

Check Digit Verification of cas no

The CAS Registry Mumber 308358-04-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,0,8,3,5 and 8 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 308358-04:
(8*3)+(7*0)+(6*8)+(5*3)+(4*5)+(3*8)+(2*0)+(1*4)=135
135 % 10 = 5
So 308358-04-5 is a valid CAS Registry Number.

308358-04-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name (1R)-pulegone oxide

1.2 Other means of identification

Product number -
Other names (R)-Pulegone Oxide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:308358-04-5 SDS

308358-04-5Upstream product

308358-04-5Relevant articles and documents

Total Synthesis of (-)-Carinatine A and (+)-Lycopladine A

Meng, Lingxing

, p. 7784 - 7789 (2016)

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

Haley, Hannah M. S.,Payer, Stefan E.,Papidocha, Sven M.,Clemens, Simon,Nyenhuis, Jonathan,Sarpong, Richmond

supporting information, p. 4732 - 4740 (2021/04/07)

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

Karella, Satish,Raghavan, Sadagopan

, (2020/08/10)

Abstract: Synthetic efforts toward the synthesis of (+)-lyconadin A are described. B-Alkyl Suzuki coupling is utilized for combining 2-iodo cyclohexenone with the piperidine subunit. The piperidine subunit is derived from 5-bromo-3-nicotinic acid, and iod

A concise asymmetric total synthesis of (+)-fawcettimine

Zeng, Xin,Jia, Zhuqing,Qiu, Fayang G.

supporting information, (2020/09/16)

A straightforward and stereocontrolled total synthesis of (+)-fawcettimine was accomplished from the known (R)-5-methyl-2-cyclohexen-one in 11 steps. The synthesis features a palladium mediated cycloalkenylation of a silyl enol ether for assembling the 6/

The first asymmetric total synthesis of lycoposerramine-R

Ishida, Hiroaki,Kimura, Shinya,Kogure, Noriyuki,Kitajima, Mariko,Takayama, Hiromitsu

, p. 7762 - 7771 (2015/07/15)

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

Yuan, Changxia,Chang, Chih-Tsung,Siegel, Dionicio

supporting information, p. 5647 - 5668 (2013/07/26)

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

Ding, Rui,Lu, Yunyu,Yao, Hequan,Sun, Bingfeng,Lin, Guoqiang

scheme or table, p. 1097 - 1100 (2012/08/28)

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

Kozak, Jennifer A.,Dake, Gregory R.

scheme or table, p. 4221 - 4223 (2009/03/11)

(Chemical Equation Presented) Alkaloids alchemy: A synthesis of the Lycopodium alkaloid (+)-fawcettidine (see structure) has been developed which requires 16 steps from (R)-(+)-pulegone as the chiral starting material. Key steps include a platinum(II)-cat

Synthesis of termini-differentiated 6-carbon stereotetrads: An alkylative oxidation strategy for preparation of the C21-C26 segment of apoptolidin

Chen, Yuzhong,Evarts Jr., Jerry B.,Torres, Eduardo,Fuchs, Philip L.

, p. 3571 - 3574 (2007/10/03)

(graph presented) Two methods have been developed for the synthesis of epoxide 36. The first uses (+)-pulegone 25 as an enantiopure starting material and introduces the requisite intricacy of target 22 in 12 operations. The second method employs an enanti

Epoxidation of α,β-Unsaturated Ketones Using Hydrogen Peroxide in the Presence of Basic Hydrotalcite Catalysts

Yamaguchi, Kazuya,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi

, p. 6897 - 6903 (2007/10/03)

The basic layered hydrotalcites have been used as catalysts for the epoxidation of α,β-unsaturated ketones in heterogeneous reaction media using hydrogen peroxide as an oxidant. A wide variety of α,β-unsaturated ketones were oxidized to the corresponding epoxyketones in excellent yields under mild reaction conditions. For example, 2-cyclohexen-1-one gave 2,3-epoxycyclohexanone in 91% yield at 40°C for 5 h with high efficiency in hydrogen peroxide. The catalytic activity of the hydrotalcites increased as the basicity of their surfaces increased. In the case of the epoxidation of less reactive substrates, adding a cationic surfactant such as n-dodecyltrimethylammonium bromide (DTMAB) to the above oxidation system accelerated the epoxidation reaction. These hydrotalcite catalysts were easily separated from the reaction mixture and were reusable.

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