99-49-0 Usage
Chemical Description
Different sources of media describe the Chemical Description of 99-49-0 differently. You can refer to the following data:
1. Carvone, 2,4-dinitro-d-traps-Carveol, and trans-carveol are organic compounds with similar structures.
2. Carvone is a chiral compound used as a starting material for the synthesis of chiral building blocks.
Chemical Properties
Different sources of media describe the Chemical Properties of 99-49-0 differently. You can refer to the following data:
1. Pale-yellowish or colorless liquid with a
strong characteristic odor. Soluble in alcohol,
ether, chloroform, propylene glycol, and mineral
oils; insoluble in glycerol and water. Combustible.
2. Carvone occurs as (S)-(+)-
carvone ([α]18
D +64.3°,), (R)-(?)-carvone ([α]20
D ?62.5°),
or racemic carvone. The optical isomers differ considerably in their
sensory properties. They occur in high percentages in a number of essential oils.
(+)-Carvone is the main component of caraway oil (about 60%) and dill oil; (?)-
carvone occurs in spearmint oil at a concentration of 70–80%.Both (+)- and (?)-carvone are used to flavor a number of foods and beverages.
(?)-Carvone is produced in much larger quantities and is mainly used in
oral hygiene products.
Physical properties
The carvones are colorless to slightly yellow liquids.(+)-Carvone has
a herbaceous odor reminiscent of caraway and dill seeds, whereas (?)-carvone has a herbaceous odor reminiscent of spearmint. Depending on the reaction conditions,
hydrogenation of carvone yields either carveol or dihydrocarvone, which
are also used as flavor compounds. When treated with strong acids, carvone isomerizes to carvacrol.
Occurrence
The optically active and inactive forms have been reported among the constituents of about 70 essential oils.
The dextro form is present in carvi, Antheum graveolens, Antheum sowa, Lippia carviodora, Mentha arvensis, etc. The levo form is
present in Metha vifidis var. crispa, Mentha longifolia from South Africa, Eucalyptus globules and several mint species. The racemic
form is present in ginger grass, Litsea gutalemaleusis, lavender and Artemisia ferganensis. Reported found in citrus oil and juice
(lemon, lime, orange), celery seed, anise, clove, coriander seed, calamus, caraway herb and dill seed.
Uses
Different sources of media describe the Uses of 99-49-0 differently. You can refer to the following data:
1. Flavoring, liqueurs, perfumery, soaps.
2. Carvone is useful for the treatment of various metabolic disorders and GI related disorders.
Definition
A ketone derived from the terpene dipentene. It is
optically active, occurring naturally in both d- and
l-forms.
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 sustainable approach towards solventless organic oxidations catalyzed by polymer immobilized Nb(V)-peroxido compounds with H2O2 as oxidant
Ahmed, Kabirun,Gogoi, Sandhya Rani,Islam, Nashreen S.,Saikia, Gangutri,Sultana, Sazida Yasmin,Talukdar, Hiya
, (2021/11/16)
New heterogeneous catalysts comprising of peroxidoniobium(V) complexes immobilized on amino acid grafted cross-linked poly(styrene-divinylbenzene) resin has been developed. Results of FTIR, Raman, NMR, XPS, XRD, EDX, SEM, BET, TGA, and elemental analysis confirmed the successful anchoring of triperoxidoniobium(V), [Nb(O2)3]? species to the host polymer via the pendant amino acid groups. The supported catalysts exhibited excellent performance in epoxidation of styrene and a range of cyclic and terpenic compounds under environmentally acceptable solvent-free condition, with aqueous H2O2 as oxidant. The catalytic protocols provided excellent conversion to the desired epoxide (up to 100%) with selectivity > 99%, TON as high as 1000, and high H2O2 utilization efficiency (92–97%). Moreover, the catalysts efficiently facilitated chemoselective solvent-free oxidation of a variety of thioethers to sulfones at room temperature. Simple operational strategy, easy recyclability for multiple reaction cycles with the consistent activity-selectivity profile are the additional significant attributes of the developed catalytic processes.
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.
