Tetrahydrocarvone

Base Information

• Chemical Name: Tetrahydrocarvone
• CAS No.: 5206-83-7
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.252
• UNII: N2VIB4RXFK,D5PYY1B83Q
• DSSTox Substance ID: DTXSID70200035
• Nikkaji Number: J247.016K
• Wikidata: Q83073064
• Mol file: 5206-83-7.mol

Synonyms:carvomenthone;p-menthan-2-one;tetrahydrocarvone

Chemical Property of Tetrahydrocarvone

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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

Technology Process of Tetrahydrocarvone

There total 45 articles about Tetrahydrocarvone 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: 53.0%

carvacrol (499-75-2) → methyl-2 isopropyl-5 cyclohexanone (499-70-7,3901-91-5,5206-83-7,7065-48-7,13163-73-0,13163-74-1,59471-80-6,116562-19-7,127911-15-3)

Guidance literature:

With C₃₃H₄₉ClNRh; hydrogen; In 2,2,2-trifluoroethanol; water; at 70 ℃; for 24h; under 60006 Torr; Autoclave;

DOI:10.1021/jacs.5b05868

Reference yield: 11.0%

(+)-neodihydrocarveol (20549-48-8,17699-09-1) → Menthane (99-82-1,1678-82-6,6069-98-3,129939-70-4,129939-71-5) + (1R,4R)-(+)-carvomenthone (5206-83-7) + (1R,2S,4R)-(+)-neocarvomenthol (3858-49-9) + (-)-(1S,2R,5S)-neoisocarvomenthol (1126-41-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In diethyl ether; at 20 ℃; under 760 Torr; Further byproducts given;

Reference yield:

(+/-)-cis-caran-trans-4-ol (4017-88-3,4017-89-4,4017-93-0,4089-03-6,13494-16-1,14727-72-1,16725-98-7,38748-96-8,52153-60-3,52194-69-1,52486-23-4,54750-08-2,54750-09-3,91422-61-6) → methyl-2 isopropyl-5 cyclohexanone (499-70-7,3901-91-5,5206-83-7,7065-48-7,13163-73-0,13163-74-1,59471-80-6,116562-19-7,127911-15-3) + cis-carane-4-one (4176-01-6,4176-04-9,13124-69-1,24278-58-8,43124-59-0,43124-60-3,52153-58-9,135559-92-1) + methyl-2 isopropyl-5 cyclohexanone (499-70-7,3901-91-5,5206-83-7,7065-48-7,13163-73-0,13163-74-1,59471-80-6,116562-19-7,127911-15-3) + 2,5,5-trimethylcycloheptanone (95242-32-3)

Guidance literature:

carbon-copper; at 320 ℃; Title compound not separated from byproducts;

upstream raw materials:

(1R,2R,4R)-(-)-carvomenthol

(R)-5-isopropyl-2-methylcyclohex-2-enone

(R)-Carvone

(1S,2S,4R)-4-isopropyl-1-methylcyclohexane-1,2-diol

Downstream raw materials:

3-<4-Isopropyl-1-methyl-2-oxo-cyclohexyl-(1)>-propionsaeure-methylester

hydroxymethylenecarvomenthone

[(2R,5R)-5-Isopropyl-2-methyl-cyclohex-(E)-ylidene]-acetic acid methyl ester

(4R,7R)-(-)-7-methyl-4-isopropyl-2-oxo-oxepanone