| Record Information |
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| Version | 2.0 |
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| Created at | 2022-03-17 20:54:39 UTC |
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| Updated at | 2026-02-12 00:01:47 UTC |
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| NP-MRD ID | NP0048324 |
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| Natural Product DOI | https://doi.org/10.57994/6375 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Matairesinol |
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| Description | Matairesinol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Matairesinol is found in Abies nephrolepis, Abies pinsapo, Anemone cernua, Arctium lappa, Berberis koreana, Beta vulgaris, Bupleurum salicifolium, Calocedrus formosana, Carthamus tinctorius, Cedrus deodara, Centaurea arenaria, Centaurea aspera, Centaurea calcitrapa, Centaurea melitensis, Centaurea nigra, Centaurea scabiosa, Centaurea scoparia, Centaurea solstitialis, Chiococca alba, Citrus sinensis, Crossosoma bigelovii, Cryptomeria japonica, Daphne feddei, Daphne oleoides, Tetradium glabrifolium, Forsythia intermedia, Forsythia koreana, Forsythia ovata, Forsythia suspensa, Forsythia viridissima, Hordeum vulgare, Ipomoea cairica, Juniperus phoenicea, Himalaiella heteromalla, Linum album, Linum flavum, Oenanthe aquatica, Persea americana, Phoenix dactylifera, Picea glauca, Picea obovata, Pinus armandii, Saussurea medusa, Saussurea salicifolia, Selaginella doederleinii , Stellera chamaejasme, Symplocos setchuensis, Taiwania cryptomerioides, Taxus cuspidata, Taxus mairei, Thuja occidentalis, Thujopsis dolabrata, Trachelospermum asiaticum, Trachelospermum axillare, Tsuga chinensis, Tsuga heterophylla, Vaccinium myrtillus, Vitis vinifera, Zanthoxylum ailanthoides, Zanthoxylum kellermanii and Zanthoxylum schinifolium. Matairesinol was first documented in 2008 (PMID: 18803219). Matairesinol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 41661373). |
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| Structure | COC1=CC(CC2C(CC3=CC(OC)=C(O)C=C3)COC2=O)=CC=C1O InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3 |
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| Synonyms | | Value | Source |
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| 4,4'-Dihydroxy-3,3'-dimethoxylignan-9,9'-olide | HMDB | | Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone, 9ci | HMDB | | Dihydro-3,4-divanillyl-2(3H)-furanone, 8ci | HMDB |
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| Chemical Formula | C20H22O6 |
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| Average Mass | 358.3851 Da |
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| Monoisotopic Mass | 358.14164 Da |
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| IUPAC Name | 3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one |
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| Traditional Name | 3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=CC(CC2C(CC3=CC(OC)=C(O)C=C3)COC2=O)=CC=C1O |
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| InChI Identifier | InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3 |
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| InChI Key | MATGKVZWFZHCLI-UHFFFAOYSA-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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| | 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 | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Lignans, neolignans and related compounds |
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| Class | Furanoid lignans |
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| Sub Class | Tetrahydrofuran lignans |
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| Direct Parent | Dibenzylbutyrolactone lignans |
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| Alternative Parents | |
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| Substituents | - Dibenzylbutyrolactone
- Lignan lactone
- Methoxyphenol
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Gamma butyrolactone
- Tetrahydrofuran
- Carboxylic acid ester
- Lactone
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Ether
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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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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