| Record Information |
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| Version | 2.0 |
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| Created at | 2021-06-20 21:25:14 UTC |
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| Updated at | 2021-06-30 00:11:49 UTC |
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| NP-MRD ID | NP0038831 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | trihydroxy-beta-ionone |
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| Provided By | JEOL Database |
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| Description | Dihydroxy-beta-ionone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. trihydroxy-beta-ionone is found in Rehmannia glutinosa and Rehmannia glutinosa var. hueichingensis.. trihydroxy-beta-ionone was first documented in 2011 (PMID: 22375391). Based on a literature review a small amount of articles have been published on Dihydroxy-beta-ionone (PMID: 25612439) (PMID: 25232801). |
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| Structure | [H]O[C@@]1(\C([H])=C(/[H])C(=O)C([H])([H])[H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] InChI=1S/C13H22O3/c1-10(14)6-9-13(16)11(2,3)7-5-8-12(13,4)15/h6,9,15-16H,5,7-8H2,1-4H3/b9-6+/t12-,13-/m1/s1 |
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| Synonyms | | Value | Source |
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| Dihydroxy-b-ionone | Generator | | Dihydroxy-β-ionone | Generator |
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| Chemical Formula | C13H22O3 |
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| Average Mass | 226.3160 Da |
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| Monoisotopic Mass | 226.15689 Da |
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| IUPAC Name | (3E)-4-[(1R,2R)-1,2-dihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-one |
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| Traditional Name | (3E)-4-[(1R,2R)-1,2-dihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-one |
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| CAS Registry Number | Not Available |
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| SMILES | [H]O[C@@]1(\C([H])=C(/[H])C(=O)C([H])([H])[H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] |
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| InChI Identifier | InChI=1S/C13H22O3/c1-10(14)6-9-13(16)11(2,3)7-5-8-12(13,4)15/h6,9,15-16H,5,7-8H2,1-4H3/b9-6+/t12-,13-/m1/s1 |
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| InChI Key | AYWGPQFATRWJMF-BHAGLWOSSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | | Species Name | Source | Reference |
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| Rehmannia glutinosa | LOTUS Database | | | Rehmannia glutinosa var. hueichingensis. | JEOL database | - Sasaki, H., et al, Phytochemistry 30, 1997 (1991)
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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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 | Sesquiterpenoids |
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| Direct Parent | Sesquiterpenoids |
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| Alternative Parents | |
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| Substituents | - Cyclofarsesane sesquiterpenoid
- Megastigmane sesquiterpenoid
- Sesquiterpenoid
- Ionone derivative
- Cyclohexanol
- Acryloyl-group
- Cyclic alcohol
- Alpha,beta-unsaturated ketone
- Tertiary alcohol
- Enone
- 1,2-diol
- Ketone
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Alcohol
- Organic oxide
- 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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| General References | - Lu Y, Li ZH, Ma L, Deng AJ, Wu F, Zhang ZH, Qin HL: [Study on chemical constituents from cultivated Gynura nepalensis]. Zhongguo Zhong Yao Za Zhi. 2014 Oct;39(19):3777-81. [PubMed:25612439 ]
- Feng WS, Li M, Zheng XK, Zhang N, Song K, Wang JC, Kuang HX: Two new ionone glycosides from the roots of Rehmannia glutinosa Libosch. Nat Prod Res. 2015;29(1):59-63. doi: 10.1080/14786419.2014.958735. Epub 2014 Sep 18. [PubMed:25232801 ]
- Li X, Zhou M, Shen P, Zhang J, Chu C, Ge Z, Yan J: [Chemical constituents from Rehmannia glutinosa]. Zhongguo Zhong Yao Za Zhi. 2011 Nov;36(22):3125-9. [PubMed:22375391 ]
- Sasaki, H., et al. (1991). Sasaki, H., et al, Phytochemistry 30, 1997 (1991). Phytochem..
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