Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-23 16:12:31 UTC |
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Update Date | 2021-09-23 16:12:31 UTC |
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HMDB ID | HMDB0302236 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | D-(+)-dihydrocarvone |
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Description | (1r,4r)-dihydrocarvone, also known as (2r,5r)-2-methyl-5-isopropenylcyclohexanone, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (1r,4r)-dihydrocarvone is considered to be an isoprenoid lipid molecule (1r,4r)-dihydrocarvone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (1r,4r)-dihydrocarvone is a herbal and minty tasting compound found in spearmint, which makes (1r,4r)-dihydrocarvone a potential biomarker for the consumption of this food product. |
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Structure | C[C@@H]1CC[C@H](CC1=O)C(C)=C InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3/t8-,9-/m1/s1 |
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Synonyms | Value | Source |
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(1R,4R)-Dihydrocarvone | ChEBI | (2R,5R)-2-Methyl-5-isopropenylcyclohexanone | ChEBI | (2R,5R)-5-Isopropenyl-2-methylcyclohexanone | ChEBI | (2R-trans)-2-Methyl-5-(1-methylvinyl)cyclohexan-1-one | ChEBI | D-Dihydrocarvone | ChEBI |
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Chemical Formula | C10H16O |
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Average Molecular Weight | 152.2334 |
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Monoisotopic Molecular Weight | 152.120115134 |
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IUPAC Name | (2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one |
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Traditional Name | (+)-dihydrocarvone |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1CC[C@H](CC1=O)C(C)=C |
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InChI Identifier | InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3/t8-,9-/m1/s1 |
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InChI Key | AZOCECCLWFDTAP-RKDXNWHRSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Menthane monoterpenoids |
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Alternative Parents | |
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Substituents | - P-menthane monoterpenoid
- Monocyclic monoterpenoid
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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D-(+)-dihydrocarvone,1TMS,isomer #1 | C=C(C)[C@@H]1CCC(C)=C(O[Si](C)(C)C)C1 | 1368.3 | Semi standard non polar | 33892256 | D-(+)-dihydrocarvone,1TMS,isomer #1 | C=C(C)[C@@H]1CCC(C)=C(O[Si](C)(C)C)C1 | 1353.2 | Standard non polar | 33892256 | D-(+)-dihydrocarvone,1TMS,isomer #1 | C=C(C)[C@@H]1CCC(C)=C(O[Si](C)(C)C)C1 | 1576.7 | Standard polar | 33892256 | D-(+)-dihydrocarvone,1TMS,isomer #2 | C=C(C)[C@H]1C=C(O[Si](C)(C)C)[C@H](C)CC1 | 1305.4 | Semi standard non polar | 33892256 | D-(+)-dihydrocarvone,1TMS,isomer #2 | C=C(C)[C@H]1C=C(O[Si](C)(C)C)[C@H](C)CC1 | 1353.4 | Standard non polar | 33892256 | D-(+)-dihydrocarvone,1TMS,isomer #2 | C=C(C)[C@H]1C=C(O[Si](C)(C)C)[C@H](C)CC1 | 1591.2 | Standard polar | 33892256 | D-(+)-dihydrocarvone,1TBDMS,isomer #1 | C=C(C)[C@@H]1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1 | 1603.3 | Semi standard non polar | 33892256 | D-(+)-dihydrocarvone,1TBDMS,isomer #1 | C=C(C)[C@@H]1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1 | 1528.8 | Standard non polar | 33892256 | D-(+)-dihydrocarvone,1TBDMS,isomer #1 | C=C(C)[C@@H]1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1 | 1741.4 | Standard polar | 33892256 | D-(+)-dihydrocarvone,1TBDMS,isomer #2 | C=C(C)[C@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)CC1 | 1540.5 | Semi standard non polar | 33892256 | D-(+)-dihydrocarvone,1TBDMS,isomer #2 | C=C(C)[C@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)CC1 | 1504.4 | Standard non polar | 33892256 | D-(+)-dihydrocarvone,1TBDMS,isomer #2 | C=C(C)[C@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)CC1 | 1747.7 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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MS | Mass Spectrum (Electron Ionization) | splash10-066r-9200000000-f04be1ac2888052faf10 | 2015-03-01 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 10V, Positive-QTOF | splash10-0udi-1900000000-8861ba576d835c24c4e2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 20V, Positive-QTOF | splash10-0zfr-9700000000-7b7dfb5b5671e2efed19 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 40V, Positive-QTOF | splash10-100r-9000000000-02b93dd813cef6744911 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 10V, Negative-QTOF | splash10-0udi-0900000000-3bdcde43911faafba8b7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 20V, Negative-QTOF | splash10-0udi-0900000000-66279fba8a75e05ec84b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 40V, Negative-QTOF | splash10-05n3-9500000000-02a124dc8509d82c4bb8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 10V, Positive-QTOF | splash10-0gws-7900000000-b08efab8959a09a26216 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 20V, Positive-QTOF | splash10-000x-9200000000-13ccbe770389182b9c06 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 40V, Positive-QTOF | splash10-0006-9000000000-4b6afc70d0efd7f97f15 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 10V, Negative-QTOF | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 20V, Negative-QTOF | splash10-0udi-1900000000-6d20364e296745592a69 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 40V, Negative-QTOF | splash10-00kn-6900000000-23186e60d8ffad674527 | 2021-10-21 | Wishart Lab | View Spectrum |
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