(-)-Carvone

Base Information

• Chemical Name: (-)-Carvone
• CAS No.: 6485-40-1
• Molecular Formula: C10H14O
• Molecular Weight: 150.22
• Hs Code.: 29142900
• European Community (EC) Number: 229-352-5
• UNII: 5TO7X34D3D
• DSSTox Substance ID: DTXSID7041413
• Nikkaji Number: J15.688D
• Wikidata: Q27089417
• Metabolomics Workbench ID: 28097
• ChEMBL ID: CHEMBL2229268
• Mol file: 6485-40-1.mol

Synonyms:(-)-Carvone;6485-40-1;l-Carvone;(R)-(-)-Carvone;(R)-2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enone;L(-)-Carvone;(R)-Carvone;Levo-carvone;(4R)-Carvone;R-(-)-Carvone;(-)-(R)-Carvone;(-)-p-Mentha-6,8-dien-2-one;Carvone, (-)-;2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5R)-;l-Carvone (natural);laevo-carvone;CHEBI:15400;(5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one;(-)-(4R)-carvone;l-p-Mentha-1(6),8-dien-2-one;UNII-5TO7X34D3D;l-1-Methyl-4-isopropenyl-6-cyclohexen-2-one;5TO7X34D3D;(R)-(-)-p-Mentha-6,8-dien-2-one;l-6,8(9)-p-Menthadien-2-one;(R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one;CARVONE, L-;EINECS 229-352-5;(4R)-(-)-Carvone;p-Mentha-6,8-dien-2-one, (-)-;Carvol;AI3-36200;(R)-5-Isopropenyl-2-methyl-2-cyclohexenone;DTXSID7041413;EC 229-352-5;(R)-5-isopropenyl-2-methylcyclohex-2-en-1-one;(5R)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one;(5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one;(4R)-p-mentha-1(6),8-dien-2-one;FEMA NO. 2249, (-)-;MFCD00001578;p-Mentha-6,8-dien-2-one, (R)-(-)-;2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)-;(R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one;2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (theta)-;r-carvone;07V;5-isopropenyl-2-methylcyclohex-2-en-1-one;(+) Carvone;CARVONE L-FORM;CARVONE [FHFI];bmse000500;Epitope ID:141509;CARVONE L-FORM [MI];(5R)-5-isopropenyl-2-methyl-cyclohex-2-en-1-one;SCHEMBL230994;(-)-CARVONE [FCC];CHEMBL2229268;DTXCID5021413;(R)-(-)-Carvone, 98%;L-Carvone, natural, 99%, FG;(-)-Carvone, analytical standard;(R)-p-mentha-6,8-dien-2-one;L-Carvone, >=97%, FCC, FG;Tox21_300931;AKOS006343214;CS-W018139;HY-W017423;LMPR0102090007;NCGC00248214-01;NCGC00254833-01;AC-13342;CAS-6485-40-1;(R)-CARVONE (CONSTITUENT OF MYRRH);C01767;D70933;EN300-298834;(R)-(-)- P-MENTHA-6,8-DIEN-2-ONE;(R)-CARVONE (CONSTITUENT OF MYRRH) [DSC];A834902;l - p - mentha - 1(6),8 - dien - 2 - one;W-104816;(-)-Carvone, primary pharmaceutical reference standard;(R)-5-Isopropenyl-2-methyl-2-cyclohexenone, Carvol;Q27089417;2-Methyl-5-(1-methylethenyl)-(R)-2-Cyclohexen-1-one;Z1201618601;(R)-2-METHYL-5-(1- METHYLETHENYL)-2-CYCLOHEXEN-1-ONE

Chemical Property of (-)-Carvone

Chemical Property:

• Appearance/Colour: clear colorless to pale yellow liquid
• Vapor Pressure: 0.4 mm Hg ( 20 °C)
• Melting Point: 25.2oC
• Refractive Index: n20/D 1.498
• Boiling Point: 230.5 °C at 760 mmHg
• Flash Point: 88.9 °C
• PSA: 17.07000
• Density: 0.94 g/cm³
• LogP: 2.48790
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 150.104465066
• Heavy Atom Count: 11
• Complexity: 223

Purity/Quality:

99% ^*data from raw suppliers

(R)-(-)-Carvone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(CC1=O)C(=C)C
• Isomeric SMILES: CC1=CC[C@H](CC1=O)C(=C)C
• Description: L-(-)-Carvone is the principal odor component of spearmint. It is with a refreshingly cool, minty odor and taste. It is used as flavor ingredient in a variety of foods and beverages, as well as in toothpaste and mouthwash. It is used as a fragrance in personal care products. It is intended for use in the manufacture of an area repellent for mosquitoes and biting flies. L-(-)-carvone is also used in agriculture as a sprout inhibitor of potatoes.
• Uses: (R)-(-)-Carvone is used in the flavor and food industry such as chewing gum additives. It is used in air freshening products such as in essential oils as well as in aromatherapy and alternative medicine. It is used to prepare carvomenthol, carvomenthone, dihydrocarvone, carveol and limonene. It reacts with lithium dimethylcuprate to place a methyl group trans to the isopropenyl group with good stereoselectivity. It is also used as a mosquito repellent and prevent premature sprouting of potatoes. Further, it is employed as an important starting material for the synthesis of enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1 and (4S,6R,7R)-trihydroxy-1-octyne derivatives. It is utilized as a vital raw material for the asymmetric total synthesis of natural products. In addition to this, it is used as a chiral starting material.

Technology Process of (-)-Carvone

There total 114 articles about (-)-Carvone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

(4R,6R)-carveol (99-48-9,1197-06-4,1197-07-5,2102-58-1,2102-59-2,5157-78-8,5503-11-7,7632-16-8,18383-51-2,22567-18-6,20307-86-2) → (R)-Carvone (6485-40-1,2244-16-8)

Guidance literature:

With oxygen; tris(triphenylphosphine)ruthenium(II) chloride; In 1,2-dichloro-ethane; under 760 Torr; Ambient temperature;

DOI:10.1039/c39810000907

Reference yield: 89.0%

(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one (36616-60-1) → (R)-Carvone (6485-40-1,2244-16-8)

Guidance literature:

With sodium hydroxide; thiourea dioxide; tetrabutylammomium bromide; In tetrahydrofuran; at 50 ℃; for 0.5h;

DOI:10.1016/S0040-4039(96)02451-3

Reference yield: 79.0%

2,3-epoxy-5-isopropenyl-2-methylcyclohexanone (677326-54-4) → (R)-Carvone (6485-40-1,2244-16-8)

Guidance literature:

With hydrogen; triethyl phosphite; In isopropyl alcohol; at 100 ℃; for 32h; under 6000.6 Torr; chemoselective reaction; Glovebox;

DOI:10.1039/d0cy01695k

upstream raw materials:

(2S,4S)-carveol

(+)-trans-carveol

oxime (4S)-4-isopropenyl-1-methylcyclohex-1-en-6-one

(1E,6R)-4,7,7-trimethylbicyclo[4.1.0]hept-4-en-3-one

Downstream raw materials:

carvacrol

(S)-8-methoxy-p-menth-6-en-2-one

(R)-5-isopropenyl-1,2-dimethyl-cyclohexa-1,3-diene

1-methyl-6-methylene-4-(prop-1-en-2-yl)cyclohex-1-ene

Refernces

Enantioselective synthesis of a key A-ring intermediate for the preparation of 1α,25-dihydroxyvitamin D₃

10.1021/ol102586w

The research focuses on the enantioselective synthesis of a key A-ring intermediate, specifically the R,β-unsaturated aldehyde 1, which is crucial for the preparation of 1α,25-dihydroxyvitamin D3 (calcitriol). The purpose of this study is to develop a novel and efficient approach to synthesize this intermediate, starting from the inexpensive material (R)-carvone, with the potential to create vitamin D3 analogues with modifications at the C-2 position. The research concludes that a new strategy has been successfully developed, which involves 11 steps and yields the desired intermediate in 24% overall yield, with the ene reaction as the key step. This method could be applied to synthesize vitamin D3 analogues with modifications at the C-2 position, which may have increased binding affinity for the vitamin D receptor (VDR) and potent agonistic activity. Key chemicals used in the process include (R)-carvone, LAH, m-CPBA, nitrobenzoate, MOM group, Zn powder, NaI, and active forms of formaldehyde, among others.

A formal total synthesis of eleutherobin using the ring-closing metathesis (RCM) reaction of a densely functionalized diene as the key step: Investigation of the unusual kinetically controlled RCM stereochemistry

10.1002/chem.200500749

The research presents a formal total synthesis of eleutherobin, a natural product with antitumor activity. The key step of the strategy involves a ring-closing metathesis (RCM) reaction of a densely functionalized diene. The study investigates the unusual kinetically controlled RCM stereochemistry using computational methods. The synthesis begins with the preparation of aldehyde 6 from R-(–)-carvone through a series of reactions, which is then converted into diene 5 via stereoselective titanium-mediated Hafner–Duthaler oxyallylation reactions. The RCM reaction of diene 5 using Grubbs' second-generation catalyst leads to the formation of the ten-membered carbocycle (E)-14, which is less thermodynamically stable but formed under kinetic control. Further transformations including removal of protective groups and oxidation lead to the key intermediate 3, which is identical to the data reported by Danishefsky and co-workers. The research also explores the stereochemical outcome of the RCM reaction and the subsequent isomerization of the enedione using molecular mechanics, semiempirical PM3 calculations, and density functional theory (DFT) calculations. The study highlights the role of the p-methoxyphenyl (PMP) protective group in facilitating the RCM reaction and the formation of the kinetically controlled E isomer.

Synthesis of the enantiomers of sclerosporin and sclerosporal to determine the absolute configuration of the natural products

10.1016/S0040-4039(01)91234-1

The study focused on the synthesis of sclerostin and enantiomers of sclerostin to determine their absolute configurations. The researchers synthesized both enantiomers from (-)-carvone using intermolecular and intramolecular Diels-Alder reactions. The key chemicals involved included (-)-carvone as a starting material, PCC-NaOAc for oxidation to form the aldehyde, methylallylmagnesium bromide for allylation, and methacrylate for the Diels-Alder reaction. The study identified (4R, 9R, 10R)-(+)-sclerostin and (4R, 9R, 10R)-(-)-sclerostin as natural enantiomers by bioassay and CD spectral comparison. The spectral data of the synthesized sclerostin and sclerostin were exactly the same as those of the authentic samples, and the study found that (+)-sclerostin had strong sporulation activity, while (-)-sclerostin only showed weak activity.

SYNTHESIS OF COMPOUNDS RELATED TO SCLEROSPORAL

10.1246/cl.1982.1715

The research aimed at synthesizing compounds related to sclerosporal, a metabolite of Sclerotinia flucticola, to confirm its proposed guaianoid structure. The researchers synthesized two optically active aldehydes, 3 and 4, which were thought to possess the planar structure for sclerosporal. Starting from (-)-carvone, various chemicals were used in the process, including 1,3-dibromo-2-pentene for alkylation, Hg(OAc)2 and HCO2H for treatment to yield diones and formates, DDQ for dehydrogenation, and Li-NH3 for reduction. The study concluded that the proposed structures for sclerosporal and sclerosporin were erroneous, as the synthetic aldehydes 3 and 4 did not match the spectral data of natural sclerosporal, necessitating a revision of the structures. The research also highlighted the importance of further studies to confirm the suggested mechanisms of the reactions involved.