| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:04:31 UTC |
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| Update date | 2019-11-26 02:54:38 UTC |
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| Primary ID | FDB000328 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Cyclolariciresinol |
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| Description | Cyclolariciresinol is a member of the class of compounds known as 9,9p-dihydroxyaryltetralin lignans. 9,9p-dihydroxyaryltetralin lignans are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position. Cyclolariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cyclolariciresinol can be found in sesame, which makes cyclolariciresinol a potential biomarker for the consumption of this food product. |
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| CAS Number | Not Available |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C20H24O6 |
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| IUPAC name | (6R,7R,8S)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol |
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| InChI Identifier | InChI=1S/C20H24O6/c1-25-18-6-11(3-4-16(18)23)20-14-8-17(24)19(26-2)7-12(14)5-13(9-21)15(20)10-22/h3-4,6-8,13,15,20-24H,5,9-10H2,1-2H3/t13-,15-,20-/m0/s1 |
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| InChI Key | OGFXBIXJCWAUCH-KPHUOKFYSA-N |
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| Isomeric SMILES | COC1=CC2=C(C=C1O)[C@@H]([C@@H](CO)[C@H](CO)C2)C1=CC=C(O)C(OC)=C1 |
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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 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position. |
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| Kingdom | Organic compounds |
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| Super Class | Lignans, neolignans and related compounds |
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| Class | Aryltetralin lignans |
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| Sub Class | 9,9p-dihydroxyaryltetralin lignans |
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| Direct Parent | 9,9p-dihydroxyaryltetralin lignans |
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| Alternative Parents | |
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| Substituents | - 9,9p-dihydroxyaryltetralin lignan
- Methoxyphenol
- Tetralin
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Ether
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Primary alcohol
- Aromatic homopolycyclic compound
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| Molecular Framework | Aromatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | Not Available |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01ox-0009000000-c62347f7d23f139500b2 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01r6-0029000000-2e701260ff02204a6db4 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-046r-1296000000-2462184e5f2381cc8003 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0009000000-f73a7a954d179ba82441 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08i3-0019000000-549e39425b6f669403a0 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03di-0049000000-a00f15bc0e90788a9ef8 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0009000000-f2b72c239d8ad9f0868e | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08i1-0029000000-1fd70a6bd2e6aaef22c4 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0bvi-0039000000-fb105fedab647c96f590 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002f-0009000000-90ecf9cf4ec9788affbb | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004l-0019000000-9e373060a35df37cf5f1 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01r6-0149000000-0f7bca44b9b554426eb0 | 2021-10-21 | 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 | Not Available |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | 617 |
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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 | Not Available |
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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 | Not Available |
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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 | 617 |
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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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| 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 |
- Smeds AI, Hakala K, Hurmerinta TT, Kortela L, Saarinen NM, Makela SI: Determination of plant and enterolignans in human serum by high-performance liquid chromatography with tandem mass spectrometric detection. J Pharm Biomed Anal. 2006 Jun 7;41(3):898-905. Epub 2006 Feb 7. Pubmed [Structure]
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| Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
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