(+)-Dihydrocarvone

Base Information

• Chemical Name: (+)-Dihydrocarvone
• CAS No.: 5524-05-0
• Molecular Formula: C10H16 O
• Molecular Weight: 152.236
• Hs Code.: 2914299000
• European Community (EC) Number: 226-872-4
• UNII: VTA43H364Z
• DSSTox Substance ID: DTXSID60895818,DTXSID80881218
• Nikkaji Number: J995.644A
• Wikidata: Q27105262
• Metabolomics Workbench ID: 28121
• ChEMBL ID: CHEMBL2268553
• Mol file: 5524-05-0.mol

Synonyms:5524-05-0;(+)-Dihydrocarvone;(1R,4R)-Dihydrocarvone;d-Dihydrocarvone;(E)-dihydrocarvone;(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexanone;CHEBI:154;(+)-trans-dihydrocarvone;UNII-VTA43H364Z;(2R,5R)-2-methyl-5-prop-1-en-2-ylcyclohexan-1-one;(2R-trans)-2-Methyl-5-(1-methylvinyl)cyclohexan-1-one;(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one;VTA43H364Z;(1R,4R)-(+)-Dihydrocarvone;(2R,5R)-5-Isopropenyl-2-methylcyclohexanone;EINECS 226-872-4;Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R,5R)-;Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R-trans)-;(2R,5R)-2-methyl-5-isopropenylcyclohexanone;5948-04-9;(+) dihydrocarvone;D-(+)-dihydrocarvone;(+/-)-dihydrocarvone;trans-(+)-dihydrocarvone;DIHYDROCARVONE, D-;Epitope ID:141511;Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, trans-;Dihydrocarvone, (+)-trans-;Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R,5R)-rel-;SCHEMBL437688;CHEMBL2268553;DTXSID60895818;DTXSID80881218;(1R,4R)-p-menth-8-en-2-one;DIHYDROCARVONE, TRANS-(+)-;LMPR0102090033;AS-63585;E85246;EN300-1608630;trans-2-Methyl-5-(1-methylethenyl)cyclohexanone;Q27105262;Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2theta-trans)-

Chemical Property of (+)-Dihydrocarvone

Chemical Property:

• Vapor Pressure: 0.107mmHg at 25°C
• Refractive Index: n20/D 1.471
• Boiling Point: 87-88oC/6mmHg
• Flash Point: 102oC
• PSA: 17.07000
• Density: 0.928 g/mL at 20oC(lit.)
• LogP: 2.56780
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

(+)-Dihydrocarvone mixture of isomers ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(CC1=O)C(=C)C
• Isomeric SMILES: C[C@@H]1CC[C@H](CC1=O)C(=C)C
• Uses: (+)-Dihydrocarvone may be used in the following processes:Synthesis of dispiro 1,2,4,5-tetraoxanes, which show potent anti-malarial activity.Synthesis of an epoxylactone by oxidation, which can undergo copolymerization with ε-caprolactone to form cross-linked copolymers with shape memory properties.Synthesis of α-Cyperone, a eudesmane type sesquiterpenoid compound with potent insecticidal activity.

Technology Process of (+)-Dihydrocarvone

There total 143 articles about (+)-Dihydrocarvone 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: 85.0%

9-isopropenyl-6-methyl-1,4-dioxa-spiro[4.5]decane (22344-27-0) → 2-methyl-5-(prop-1-en-2-yl)cyclohexanone (3792-53-8,4584-09-2,5524-05-0,5948-04-9,6909-25-7,7764-50-3,53796-79-5,69460-46-4,116499-64-0,619-02-3,619-01-2)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; at -20 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.10.037

Reference yield: 78.0%

(4R)‐1‐methyl‐4‐(prop‐1‐en‐2‐yl)‐7‐oxabicyclo[4.1.0]heptane → 2-methyl-5-(prop-1-en-2-yl)cyclohexanone (3792-53-8,4584-09-2,5524-05-0,5948-04-9,6909-25-7,7764-50-3,53796-79-5,69460-46-4,116499-64-0,619-02-3,619-01-2)

Guidance literature:

With acetylacetone; zinc dibromide; at 155 - 160 ℃; for 3h; Temperature; Reagent/catalyst;

Reference yield: 25.0%

Carvone (99-49-0,22327-39-5) → 2-methyl-5-(prop-1-en-2-yl)cyclohexanone (3792-53-8,4584-09-2,5524-05-0,5948-04-9,6909-25-7,7764-50-3,53796-79-5,69460-46-4,116499-64-0,619-02-3,619-01-2) + carvomenthone (499-70-7)

Guidance literature:

With LaNi₅ hydride; In tetrahydrofuran; methanol; at 0 ℃; for 3h;

DOI:10.1021/jo00235a009

upstream raw materials:

(S)-p-mentha-6,8-dien-2-one

(1S,2S,5S)-5-isopropenyl-2-methylcyclohexan-1-ol

(S)-p-mentha-6,8-dien-2-one-(Z)-oxime

Limonene oxide

Downstream raw materials:

p-menth-3-en-2-one

eudesma-4,11-dien-3-one

(-)-carvomenthone

caran-2-one

Refernces

• 1、 Hirata, Toshifumi,Tang, Yixiong,Okano, Kuniko,Suga, Takayuki. "STEREOCHEMISTRY OF REDUCTION OF THE ENDOCYCLIC DOUBLE BOND OF (-)-CARVONE WITH THE ENZYME PREPARATION FROM CULTURED CELLS OF NICOTIANA TABACUM". . p. 3331 - 3334. Retrieved 1989.
• 2、 M?hler, Christoph,Kratzl, Franziska,Vogel, Melina,Vinnenberg, Stefan,Weuster-Botz, Dirk,Castiglione, Kathrin. "Loop Swapping as a Potent Approach to Increase Ene Reductase Activity with Nicotinamide Adenine Dinucleotide (NADH)". . p. 2505 - 2513. Retrieved 2019.
• 3、 Nett, Nathalie,Duewel, Sabine,Schmermund, Luca,Benary, Gerrit E.,Ranaghan, Kara,Mulholland, Adrian,Opperman, Diederik J.,Hoebenreich, Sabrina. "A robust and stereocomplementary panel of ene-reductase variants for gram-scale asymmetric hydrogenation". . . Retrieved 2021/01/25.