| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-03 19:34:23 UTC |
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| Updated at | 2022-09-03 19:34:23 UTC |
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| NP-MRD ID | NP0181112 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1s,5r,6r)-5-hydroxy-3-(hydroxymethyl)-6-isopropyl-4-oxocyclohex-2-en-1-yl acetate |
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| Description | Acetic acid 3-(hydroxymethyl)-4-oxo-5alpha-hydroxy-6beta-isopropyl-2-cyclohexen-1beta-yl ester 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. (1s,5r,6r)-5-hydroxy-3-(hydroxymethyl)-6-isopropyl-4-oxocyclohex-2-en-1-yl acetate is found in Sphaeranthus suaveolens. Based on a literature review very few articles have been published on Acetic acid 3-(hydroxymethyl)-4-oxo-5alpha-hydroxy-6beta-isopropyl-2-cyclohexen-1beta-yl ester. |
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| Structure | CC(C)[C@H]1[C@@H](OC(C)=O)C=C(CO)C(=O)[C@@H]1O InChI=1S/C12H18O5/c1-6(2)10-9(17-7(3)14)4-8(5-13)11(15)12(10)16/h4,6,9-10,12-13,16H,5H2,1-3H3/t9-,10-,12+/m0/s1 |
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| Synonyms | | Value | Source |
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| Acetate 3-(hydroxymethyl)-4-oxo-5a-hydroxy-6b-isopropyl-2-cyclohexen-1b-yl ester | Generator | | Acetate 3-(hydroxymethyl)-4-oxo-5alpha-hydroxy-6beta-isopropyl-2-cyclohexen-1beta-yl ester | Generator | | Acetate 3-(hydroxymethyl)-4-oxo-5α-hydroxy-6β-isopropyl-2-cyclohexen-1β-yl ester | Generator | | Acetic acid 3-(hydroxymethyl)-4-oxo-5a-hydroxy-6b-isopropyl-2-cyclohexen-1b-yl ester | Generator | | Acetic acid 3-(hydroxymethyl)-4-oxo-5α-hydroxy-6β-isopropyl-2-cyclohexen-1β-yl ester | Generator |
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| Chemical Formula | C12H18O5 |
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| Average Mass | 242.2710 Da |
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| Monoisotopic Mass | 242.11542 Da |
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| IUPAC Name | (1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-4-oxo-6-(propan-2-yl)cyclohex-2-en-1-yl acetate |
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| Traditional Name | (1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-isopropyl-4-oxocyclohex-2-en-1-yl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)[C@H]1[C@@H](OC(C)=O)C=C(CO)C(=O)[C@@H]1O |
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| InChI Identifier | InChI=1S/C12H18O5/c1-6(2)10-9(17-7(3)14)4-8(5-13)11(15)12(10)16/h4,6,9-10,12-13,16H,5H2,1-3H3/t9-,10-,12+/m0/s1 |
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| InChI Key | QEKUAMYPTPQAPS-JBLDHEPKSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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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 | - Monocyclic monoterpenoid
- P-menthane monoterpenoid
- Cyclohexenone
- Carboxylic acid ester
- Ketone
- Secondary alcohol
- Cyclic ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Primary alcohol
- Organooxygen compound
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- Aliphatic homomonocyclic compound
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| Molecular Framework | Aliphatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental 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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| Predicted Properties | |
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