d-Carvone

Base Information

• Chemical Name: d-Carvone
• CAS No.: 2244-16-8
• Deprecated CAS: 53763-73-8
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.221
• Hs Code.: 29142900
• European Community (EC) Number: 218-827-2
• UN Number: 2810
• UNII: 4RWC1CMS3X
• DSSTox Substance ID: DTXSID8020256
• Nikkaji Number: J9.490K
• Wikidata: Q27889969
• Metabolomics Workbench ID: 38529
• ChEMBL ID: CHEMBL501949
• Mol file: 2244-16-8.mol

Synonyms:d-Carvone;2244-16-8;(+)-Carvone;(S)-(+)-Carvone;(S)-Carvone;(S)-2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enone;D(+)-Carvone;(+)-(S)-Carvone;Carvone, (+)-;D-(+)-Carvone;(S)-(+)-p-Mentha-6,8-dien-2-one;S-(+)-carvone;Carvol;d-Carvone (natural);(+)-(4S)-carvone;(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one;p-Mentha-6,8-dien-2-one, (S)-(+)-;2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5S)-;CCRIS 2385;d-1-Methyl-4-isopropenyl-6-cyclohexen-2-one;Talent;CHEBI:15399;UNII-4RWC1CMS3X;2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (S)-;4RWC1CMS3X;(S)-d-p-Mentha-6,8,(9)-dien-2-one;(S)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-one;EINECS 218-827-2;d-p-Mentha-6,8,(9)-dien-2-one;(4S)-carvone;DTXSID8020256;AI3-39004;CARVONE D-;CARVONE, D-;DTXCID00256;(5S)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one;(5S)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one;(S)-2-methyl-5-(1-methylethenyl)-2-Cyclohexen-1-one;(S)-5-Isopropenyl-2-methyl-2-cyclohexenone;(S)-5-isopropenyl-2-methylcyclohex-2-en-1-one;d-p-Mentha-6,8(9)-dien-2-one;(4S)-p-mentha-1(6),8-dien-2-one;FEMA NO. 2249, (+)-;(5S)-2-methyl-5-(1-methylethenyl)cyclohex-2-en-1-one;MFCD00062997;CAS-2244-16-8;(S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one;dextro-carvone;s-carvone;d-carvon;(+)carvone;5-isopropenyl-2-methylcyclohex-2-en-1-one;S(+)-Carvone;carvone, (S)-isomer;D-CARVOL;CARVONE D-FORM;Epitope ID:141510;CARVONE D-FORM [MI];MLS002415723;SCHEMBL184022;(+)-CARVONE [FCC];D-Carvone, >=96%, FG;2-Methyl-4-(1 -methylethenyl)-2-cyclohexene-1 -one;CHEMBL501949;(5S)-2-methyl-5-(1-methylvinyl)cyclohex-2-en-1-one;(S)-(+)-Carvone, 96%;(+)-Carvone, analytical standard;HMS3039E10;LS-73;Tox21_201441;Tox21_302743;s6049;AKOS016843871;AM84798;CS-W014295;DS-4662;HY-W013579;6-allyl-4,5-dimethoxy-1,3-benzodioxol;NCGC00091882-01;NCGC00091882-02;NCGC00091882-03;NCGC00091882-04;NCGC00256315-01;NCGC00258992-01;(S)-(+)-p-mentha-6,8-dien- 2-one;SMR001370898;p-Mentha-6,8-dien-2-one, (S)-()-;EN300-393032;O10215;A816212;5-Isopropenyl-2-methyl-2-cyclohexen-1-one, (S)-;Q-200930;Q27889969;Z1255356261;(+)-Carvone, certified reference material, TraceCERT(R);D-Carvone 2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-one;(S) - 2 - methyl - 5 - (1 - methylvinyl)cyclohex - 2 - en - 1 - one;0WU

Chemical Property of d-Carvone

Chemical Property:

• Appearance/Colour: colourless or pale yellow liquid
• Vapor Pressure: 0.0656mmHg at 25°C
• Melting Point: 88.9°C
• Refractive Index: n20/D 1.499
• Boiling Point: 230.5 °C at 760 mmHg
• Flash Point: 88.9 °C
• PSA: 17.07000
• Density: 0.94 g/cm³
• LogP: 2.48790
• Water Solubility.: <0.1 g/100 mL at 25℃
• 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
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CCC(CC1=O)C(=C)C
• Isomeric SMILES: CC1=CC[C@@H](CC1=O)C(=C)C

Technology Process of d-Carvone

There total 114 articles about d-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

Rapid construction of [5-6-7] tricyclic ring skeleton of calyciphylline alkaloid daphnilongeranin B

10.1021/ol200312q

The research focuses on the rapid construction of the [5-6-7] tricyclic ring skeleton of Calyciphylline alkaloids, specifically targeting Daphnilongeranin B. The study employs a concise photochemical [2+2] cycloaddition-Grob fragmentation sequence to synthesize the common tricyclic ring skeletons found in Calyciphylline A-type alkaloids, including daphnilongeranins, daphniyunnines, and daphniglaucins. The experiments utilize key steps such as Overman rearrangement, Mannich reaction, [2+2] photochemical cycloaddition, and Grob fragmentation. Reactants include (S)-(+)-carvone as the starting material, which is converted through a series of reactions involving CCl3CN, MOMCl, TBSOTf, and other reagents to construct the tricyclic core. The analyses used to confirm the structures and stereochemistry of the synthesized compounds include single crystal X-ray analysis and NMR spectroscopy, with detailed experimental procedures and compound characterization data provided in the supporting information.

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