Dihydrocarvone

Base Information

• Chemical Name: Dihydrocarvone
• CAS No.: 7764-50-3
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• Hs Code.: 2914299000
• European Community (EC) Number: 231-857-0,611-836-6
• DSSTox Substance ID: DTXSID00863556
• Nikkaji Number: J150.037F,J87.284I
• Wikidata: Q27109809
• Mol file: 7764-50-3.mol

Synonyms:2-methyl-5-(1-methylethenyl)cyclohexanone;3-isopropenyl-6-methylcyclohexanone;dihydrocarvone;p-menth-8-en-2-one

Chemical Property of Dihydrocarvone

Chemical Property:

• Appearance/Colour: almost colourless liquid with a herbaceous, spearmint-like odour
• Vapor Pressure: 0.06 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.472(lit.)
• Boiling Point: 87-88 °C6 mm Hg(lit.)
• Flash Point: 178 °F
• PSA: 17.07000
• Density: 0.929 g/mL at 25 °C(lit.)
• LogP: 2.56780
• Storage Temp.: 2-8°C
• 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:

98%,99%, ^*data from raw suppliers

D-Dihydrocarvone, mixture of isomers ≥97%, FCC, FG ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC(CC1=O)C(=C)C
• Uses: The dual, herbal-minty quality of this compound will add an interesting twist to mint flavors as well as to celery, caraway, dill and herbal flavors, especially intended for cough drops and oral care products. At very low levels, it will add depth to tropical flavors like lychee, guava, passion fruit and rambutan. The N-functionalization of dihydrocarvone forms imine derivatives, which are synthons for preparing N-heterocycles.

Technology Process of Dihydrocarvone

There total 76 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: 95.0%

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)

Guidance literature:

With tri-n-butyl-tin hydride; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)86751-9

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: 79.0%

limonene. (138-86-3,555-08-8,8022-90-0,9003-73-0,95327-98-3) → 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:

limonene.; With Acetoxyboran; In tetrahydrofuran; at 20 ℃; for 16h;

With pyridinium chlorochromate; In dichloromethane; for 1h; Heating;

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

(+)-neodihydrocarveol

dihydrocarveol

carvomenthone

Refernces

• 1、 Rüthi, Fabian,Schr?der, Fridtjof. "Total Synthesis of (?)-Rotundone and (?)-epi-Rotundone from Monoterpene Precursors". . . Retrieved 2020/10/30.
• 2、 Issa, Issa S.,Toogood, Helen S.,Johannissen, Linus O.,Raftery, James,Scrutton, Nigel S.,Gardiner, John M.. "C3 and C6 Modification-Specific OYE Biotransformations of Synthetic Carvones and Sequential BVMO Chemoenzymatic Synthesis of Chiral Caprolactones". supporting information. p. 2983 - 2988. Retrieved 2019/01/24.