Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 00:50:50 UTC |
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Updated at | 2022-09-12 00:50:50 UTC |
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NP-MRD ID | NP0322205 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | {4'-[hydroxy(oxiran-2-yl)methyl]-2,2',6,6'-tetramethoxy-[1,1'-biphenyl]-4-yl}(oxiran-2-yl)methanol |
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Description | 2,6,2',6'-Tetramethoxy-4,4'-bis(2,3-epoxy-1-hydroxypropyl)biphenyl belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. {4'-[hydroxy(oxiran-2-yl)methyl]-2,2',6,6'-tetramethoxy-[1,1'-biphenyl]-4-yl}(oxiran-2-yl)methanol is found in Hypericum geminiflorum and Vincetoxicum atratum. 2,6,2',6'-Tetramethoxy-4,4'-bis(2,3-epoxy-1-hydroxypropyl)biphenyl is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | COC1=CC(=CC(OC)=C1C1=C(OC)C=C(C=C1OC)C(O)C1CO1)C(O)C1CO1 InChI=1S/C22H26O8/c1-25-13-5-11(21(23)17-9-29-17)6-14(26-2)19(13)20-15(27-3)7-12(8-16(20)28-4)22(24)18-10-30-18/h5-8,17-18,21-24H,9-10H2,1-4H3 |
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Synonyms | Not Available |
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Chemical Formula | C22H26O8 |
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Average Mass | 418.4420 Da |
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Monoisotopic Mass | 418.16277 Da |
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IUPAC Name | (4-{4-[hydroxy(oxiran-2-yl)methyl]-2,6-dimethoxyphenyl}-3,5-dimethoxyphenyl)(oxiran-2-yl)methanol |
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Traditional Name | (4-{4-[hydroxy(oxiran-2-yl)methyl]-2,6-dimethoxyphenyl}-3,5-dimethoxyphenyl)(oxiran-2-yl)methanol |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(=CC(OC)=C1C1=C(OC)C=C(C=C1OC)C(O)C1CO1)C(O)C1CO1 |
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InChI Identifier | InChI=1S/C22H26O8/c1-25-13-5-11(21(23)17-9-29-17)6-14(26-2)19(13)20-15(27-3)7-12(8-16(20)28-4)22(24)18-10-30-18/h5-8,17-18,21-24H,9-10H2,1-4H3 |
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InChI Key | FQTWUNWPYHHEKJ-UHFFFAOYSA-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 lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Not Available |
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Sub Class | Not Available |
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Direct Parent | Lignans, neolignans and related compounds |
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Alternative Parents | |
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Substituents | - Neolignan skeleton
- Biphenyl
- Dimethoxybenzene
- M-dimethoxybenzene
- Methoxybenzene
- Anisole
- Phenol ether
- Phenoxy compound
- Alkyl aryl ether
- Benzenoid
- Monocyclic benzene moiety
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Ether
- Oxirane
- Dialkyl ether
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Aromatic alcohol
- Alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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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