Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2012-09-11 20:42:38 UTC |
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Update Date | 2020-11-09 23:20:34 UTC |
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HMDB ID | HMDB0035698 |
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Secondary Accession Numbers | - HMDB0035789
- HMDB35698
- HMDB35789
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Metabolite 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, matairesinol is found, on average, in the highest concentration in a few different foods such as sesame, burdocks, and flaxseeds, and in a lower concentration in oats, asparagus, and poppies. Matairesinol has also been detected, but not quantified in, several different foods, such as silver lindens, tamarinds, cherry tomato, skunk currants, and fireweeds. This could make matairesinol a potential biomarker for the consumption of these foods. Matairesinol is composed of gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer). |
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Structure | |
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Synonyms | Value | Source |
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3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanone | ChEBI | Artigenin congener | ChEBI | Matairesinol | ChEBI | (3R,4R)-3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one | Kegg | (8R,8'r)-(-)-Matairesinol | HMDB | Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-furanone | HMDB | Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-furanone | HMDB | Matai-resinol | HMDB | (-)-Matairesinol | KEGG | (3R,4R)-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone | HMDB | (8R,8’R)-(-)-Matairesinol | HMDB | Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone | HMDB | Dihydro-3,4-divanillyl-2(3H)-furanone | PhytoBank |
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Chemical Formula | C20H22O6 |
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Average Molecular Weight | 358.3851 |
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Monoisotopic Molecular Weight | 358.141638436 |
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IUPAC Name | (3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one |
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Traditional Name | matairesinol |
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CAS Registry Number | 580-72-3 |
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SMILES | COC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C1 |
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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/t14-,15+/m0/s1 |
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InChI Key | MATGKVZWFZHCLI-LSDHHAIUSA-N |
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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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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 119 °C | 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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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-000i-0912000000-7b4af0e03073d528f059 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-052o-1050900000-0801cdc5bc6f2e25f382 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0229000000-da790a5b3ff80ab843dc | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06ri-0978000000-407d81dd6dfadba216c4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ims-1910000000-060bdfec7823f760bd09 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0009000000-25c656431001e8e5785f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bt9-0129000000-eefe04935cde889de64c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01ot-0986000000-2b1737e1ecb9a7ee39f9 | Spectrum |
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General References | - Muller U, Mrestani Y, Neubert R, Drager B: Chiral separation of the plant lignan matairesinol by capillary electrophoresis. Electrophoresis. 2008 Sep;29(17):3582-7. doi: 10.1002/elps.200700800. [PubMed:18803219 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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