Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:44 UTC |
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Update date | 2019-11-26 03:05:09 UTC |
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Primary ID | FDB011629 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (-)-Lariciresinol |
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Description | (-)-lariciresinol is a member of the class of compounds known as 7,9'-epoxylignans. 7,9'-epoxylignans are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (-)-lariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-lariciresinol can be found in a number of food items such as cassava, acorn, celeriac, and banana, which makes (-)-lariciresinol a potential biomarker for the consumption of these food products. |
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CAS Number | 83327-19-9 |
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Structure | |
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Synonyms | Synonym | Source |
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Not Available | Not Available |
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Predicted Properties | |
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Chemical Formula | C20H24O6 |
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IUPAC name | 4-{4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl}-2-methoxyphenol |
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InChI Identifier | InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3 |
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InChI Key | MHXCIKYXNYCMHY-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=CC(CC2COC(C2CO)C2=CC=C(O)C(OC)=C2)=CC=C1O |
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Average Molecular Weight | 360.401 |
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Monoisotopic Molecular Weight | 360.1572885 |
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Classification |
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Description | Belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. |
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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 | 7,9'-epoxylignans |
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Alternative Parents | |
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Substituents | - 7,9p-epoxylignan
- Methoxyphenol
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Tetrahydrofuran
- Oxacycle
- Dialkyl ether
- Ether
- Organoheterocyclic compound
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Primary 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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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 66.65%; H 6.71%; O 26.64% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D -17.8 (Me2CO) | DFC |
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Spectroscopic UV Data | 283 (e 10500) (MeOH) (Berdy) | DFC |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | (-)-Lariciresinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001r-1927000000-001aebbbc4190b3cd4d6 | Spectrum | Predicted GC-MS | (-)-Lariciresinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (-)-Lariciresinol, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0609000000-f7b88f3b846a43fa7e5d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Negative | splash10-004i-0609000000-497ccc5bdc45a10d3516 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0009000000-a75389de6f0f97063fff | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-03di-0900000000-dd554fba6f34415f2aad | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-03fr-0900000000-718d40dc06914aa1fc69 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-08fr-0900000000-faa89b1aa0b3f4c77d4e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0709000000-a6fb001327c41202d60b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-08fr-0900000000-494abb3f4b6c4c4e00b1 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0bt9-0900000000-91baad059be3220ac9d7 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-03fr-0900000000-ccb216f23e4ecfd6f5f2 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0009000000-a8f1982bd91bba2f61ea | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0609000000-6b93e74aba9c3378e7bd | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0009000000-fb84486be61c014aa09f | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03dl-0119000000-64f05aa45bb6e77829b3 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03du-0779000000-a8301760f53bcf9f1203 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01p9-1901000000-65f618ede698063b43d2 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03dl-0119000000-64f05aa45bb6e77829b3 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03du-0779000000-a8301760f53bcf9f1203 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01p9-1901000000-65f618ede698063b43d2 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0009000000-3ffeb6c4aaa793d3af6b | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bvl-0019000000-c2cca8faa0927f1ba6ee | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03dl-1925000000-204c3f64a4b6834c4b0e | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0009000000-3ffeb6c4aaa793d3af6b | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bvl-0019000000-c2cca8faa0927f1ba6ee | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03dl-1925000000-204c3f64a4b6834c4b0e | 2015-05-27 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 134203 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 544854 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | LKK06-K:GVY27-F |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000603 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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