99-49-0 Usage
Chemical Description
Carvone, 2,4-dinitro-d-traps-Carveol, and trans-carveol are organic compounds with similar structures.
Chemical Description
Carvone is a chiral compound used as a starting material for the synthesis of chiral building blocks.
Description
Carvone is a ketone derived from the terpene dipentene, which is optically active and occurs naturally in both dand l-forms. It is a pale-yellowish or colorless liquid with a strong characteristic odor. Carvone is soluble in alcohol, ether, chloroform, propylene glycol, and mineral oils but insoluble in glycerol and water. The optical isomers, (+)-carvone and (-)-carvone, differ considerably in their sensory properties and are found in various essential oils.
Uses
Used in Flavoring Industry:
Carvone is used as a flavoring agent for various foods and beverages due to its strong characteristic odor. (+)-Carvone is the main component of caraway oil (about 60%) and dill oil, while (-)-carvone occurs in spearmint oil at a concentration of 70-80%.
Used in Liqueurs:
Carvone is used in the production of liqueurs to impart a unique flavor and aroma.
Used in Perfumery:
Due to its strong and characteristic odor, carvone is used in the perfumery industry to create various fragrances.
Used in Soaps:
Carvone is used in the production of soaps to provide a pleasant scent and enhance the sensory experience of using the product.
Used in Oral Hygiene Products:
(-)-Carvone, which is produced in much larger quantities, is mainly used in oral hygiene products such as mouthwashes and toothpastes for its refreshing and minty flavor.
Used in Treatment of Metabolic and GI Disorders:
Carvone is useful for the treatment of various metabolic disorders and gastrointestinal-related disorders, although the specific applications and reasons are not detailed in the provided materials.
Preparation
In the past, (+)- and (?)-carvones were isolated by fractional distillation
of caraway oil and spearmint oil, respectively. However, these carvones are
now prepared synthetically, the preferred starting materials being (+)- and (?)-
limonenes, which are converted into the corresponding optically active carvones.
Since optical rotation is reversed in the process, (+)-limonene is the startingmaterial
for (?)-carvone.
Thepreferred industrialmethod of carvone synthesis utilizes the selective addition
of nitrosyl chloride to the endocyclic double bond of limonene. If a lower
aliphatic alcohol is used as solvent, limonene nitrosochloride is obtained in high
yield. It is converted into carvone oxime by elimination of hydrogen chloride in
the presence of a weak base. Acid hydrolysis in the presence of a hydroxylamine
acceptor, such as acetone, yields carvone.
An alternative process for the production of (?)-carvone has recently been commercialized.
Starting from (+)-limonene 1,2-epoxide, a regioselective rearrangement
of the epoxide leads to (?)-carveol (trans- :[2102-58-1]; cis- :[2102-59-2]).
Thereaction is effected by the use of a catalyst consisting of a combination of metal
salts and phenolic compounds.
(?)-Carveol is subsequently oxidized to (?)-carvone by anOppenauer oxidation
or by dehydrogenation in the presence of special catalysts.The reaction may also
be performed as a one-pot reaction.
Synthesis Reference(s)
The Journal of Organic Chemistry, 49, p. 3435, 1984 DOI: 10.1021/jo00192a054Synthesis, p. 223, 1980 DOI: 10.1055/s-1980-28975
Check Digit Verification of cas no
The CAS Registry Mumber 99-49-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 9 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 99-49:
(4*9)+(3*9)+(2*4)+(1*9)=80
80 % 10 = 0
So 99-49-0 is a valid CAS Registry Number.
99-49-0Relevant articles and documents
An aerobic oxidation of alcohols into carbonyl synthons using bipyridyl-cinchona based palladium catalyst
Cheedarala, Ravi Kumar,Chidambaram, Ramasamy R.,Siva, Ayyanar,Song, Jung Il
, p. 32942 - 32954 (2021/12/02)
We have reported an aerobic oxidation of primary and secondary alcohols to respective aldehydes and ketones using a bipyridyl-cinchona alkaloid based palladium catalytic system (PdAc-5) using oxygen at moderate pressure. ThePdAc-5catalyst was analysed using SEM, EDAX, and XPS analysis. The above catalytic system is used in experiments for different oxidation systems which include different solvents, additives, and bases which are cheap, robust, non-toxic, and commercially available on the industrial bench. The obtained products are quite appreciable in both yield and selectivity (70-85%). In addition, numerous important studies, such as comparisons with various commercial catalysts, solvent systems, mixture of solvents, and catalyst mole%, were conducted usingPdAc-5. The synthetic strategy of oxidation of alcohol into carbonyl compounds was well established and all the products were analysed using1H NMR,13CNMR and GC-mass analyses.
A silicododecamolybdate/pyridinium-tetrazole hybrid molecular salt as a catalyst for the epoxidation of bio-derived olefins
Nunes, Martinique S.,Neves, Patrícia,Gomes, Ana C.,Cunha-Silva, Luís,Lopes, André D.,Valente, Anabela A.,Pillinger, Martyn,Gon?alves, Isabel S.
, (2020/11/27)
The hybrid polyoxometalate (POM) salt (Hptz)4[SiMo12O40]?nH2O (1) (ptz = 5-(2-pyridyl)tetrazole) has been prepared, characterized by X-ray crystallography, and examined as a catalyst for the epoxidation of cis-cyclooctene (Cy) and bio-derived olefins, namely dl-limonene (Lim; a naturally occurring monoterpene found in the rinds of citrus fruits), methyl oleate and methyl linoleate (fatty acid methyl esters (FAMEs) obtained by transesterification of vegetable oils). The crystal structure of 1 consists of α-Keggin-type heteropolyanions, [SiMo12O40]4-, surrounded by space-filling and charge-balancing 2-(tetrazol-5-yl)pyridinium (Hptz+) cations, as well as by a large number of water molecules of crystallization (n = 9). The water molecules mediate an extensive three-dimensional (3D) hydrogen-bonding network involving the inorganic anions and organic cations. For the epoxidation of the model substrate Cy in a nonaqueous system (tert-butylhydroperoxide as oxidant), the catalytic performance of 1 (100% epoxide yield at 24 h, 70 °C) was superior to that of the tetrabutylammonium salt (Bu4N)4[SiMo12O40] (2) (63% epoxide yield at 24 h), illustrating the role of the counterion Hptz+ in enhancing catalytic activity. The hybrid salt 1 was effective for the epoxidation of Lim (69%/85% conversion at 6 h/24 h) and the FAMEs (87–88%/100% conversion at 6 h/24 h), leading to useful bio-based products (epoxides, diepoxides and diol products).
Selective Allylic Oxidation of Terpenic Olefins Using Co-Ag Supported on SiO2 as a Novel, Efficient, and Recyclable Catalyst
Aberkouks, Abderrazak,Mekkaoui, Ayoub Abdelkader,Ait Ali, Mustapha,El Firdoussi, Larbi,El Houssame, Soufiane
, (2020/02/15)
Co-Ag supported on the SiO2 catalyst was synthesized by the sol-gel method and characterized using XRD, FT-IR, TG-DTG, BET, CV, and SEM/EDX analysis. The catalytic performance of the resulting catalyst was examined by the oxidation of mono and sesquiterpenic olefins using hydrogen peroxide and tert-butyl peroxide as oxidant agents. Various parameters such as catalyst amount, temperature, and solvents have been studied. The Co-Ag supported on the SiO2 catalyst showed a high activity, selectivity, and recyclability for the selected oxidation reaction.
