| Identification | Back Directory | [Name]
(+)-DIHYDROCARVONE MIXTURE OF ISOMERS | [CAS]
5524-05-0 | [Synonyms]
Carvone,dihydro-
8-p-Menthen-2-one
(+)-Dihydrocarvone
2R,5R-DIHYDROCARVONE
trans-Dihydrocarvone
p-Menth-8(9)-en-2-one
p-Menth-8-en-2-one,trans-
(1R,4R)-(+)-Dihydrocarvone
(2theta-trans)-cyclohexanon
(+)-dihydrocarvone,mixtureofisomers
(2R)-2α-Methyl-5β-isopropenylcyclohexanone
(2R,5R)-2-Methyl-5-isopropenylcyclohexanone
(2R,5R)-2-Methyl-5-(prop-1-en-2-yl)cyclohexanone
(2R)-2α-Methyl-5β-(1-methylethenyl)cyclohexanone
(2R,5R)-2-Methyl-5-(1-methylethenyl)cyclohexanone
Cyclohexanone,2-methyl-5-(1-methylethenyl)-,trans-
(2R-trans)-2-methyl-5-(1-methylvinyl)cyclohexan-1-one
2-methyl-5-(1-methylethenyl)-,(2R-trans)-Cyclohexanone
Cyclohexanone,2-methyl-5-(1-methylethenyl)-,(2R,5R)-rel-
DIHYDROCARVONE/2-METHYL-5-(1-METHYLETHENYL)-,(2R-TRANS)-CYCLOHEXANONE | [EINECS(EC#)]
226-872-4 | [Molecular Formula]
C10H16O | [MDL Number]
MFCD00001636 | [MOL File]
5524-05-0.mol | [Molecular Weight]
152.233 |
| Questions And Answer | Back Directory | [Synthesis]
A method for synthesizing (+)-Dihydrocarvone from limonene oxide includes the following steps: 
Step 1: Add 300g of limonene oxide to a 500 mL reactor, and add 3g of ZnBr2 while stirring. Then raise the temperature to 140-145℃ and react for about 3 hours. After GC analysis shows that the reaction is complete, add 30g of white oil to the reaction solution and perform vacuum distillation to obtain 200g of (+)-DIHYDROCARVONE MIXTURE OF ISOMERS product. The GC analysis shows that the content is 97.5%, and the product yield is 67%. Step 2: Add 50g of the distillate (containing white oil) obtained from the above distillation to a 500mL reactor, then add 300g of epoxidized limonene. React at 140-145℃ for approximately 4 hours. After GC analysis, perform vacuum distillation to obtain 195g of (+)-DIHYDROCARVONE MIXTURE OF ISOMERS product. The GC analysis showed a purity of 97%, and the product yield was 65%. Step 2 was repeated twice, with the reaction time extended by approximately one hour each time. The results showed an average purity of 97% and a yield of 64.5%. Step 2 was then repeated twice more, with the reaction time extended by approximately one hour each time. The results showed an average purity of 97% and a yield of 63.5%. The catalytic efficiency did not decrease significantly. |
| Chemical Properties | Back Directory | [Appearance]
clear liquid | [alpha ]
+17°(22℃,neat) | [Boiling point ]
87-88°C/6mmHg | [density ]
0.928 g/mL at 20 °C(lit.)
| [FEMA ]
3565 | P-MENTH-8-EN-2-ONE | [refractive index ]
n20/D 1.471
| [Fp ]
102 °C | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
Liquid | [color ]
Clear | [Specific Gravity]
0.929 | [Odor]
at 100.00 %. herbal minty mentholic | [Odor Type]
minty | [Optical Rotation]
[α]20/D +20±2°, neat | [JECFA Number]
377 | [BRN ]
2044615 | [LogP]
3.225 (est) | [EPA Substance Registry System]
Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R,5R)- (5524-05-0) |
| Hazard Information | Back Directory | [Chemical Properties]
clear liquid | [Definition]
ChEBI: A dihydrocarvone in (R,R) configuration. | [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.
| [General Description]
(+)-Dihydrocarvone, a monoterpenoid compound found in caraway oil, is a key building block to synthesize sesquiterpenes. It is generally produced either by the hydrogenation of carvone or oxidation of limonene. |
|
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