Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:13:47 UTC |
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Update date | 2019-11-26 03:16:20 UTC |
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Primary ID | FDB018565 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 4-[(6,7-Dihydroxy-3,7-dimethyl-2-octenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one |
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Description | 6',7'-Dihydroxybergamottin, also known as lepiochlorin, belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. 6',7'-Dihydroxybergamottin is an extremely weak basic (essentially neutral) compound (based on its pKa). 6',7'-Dihydroxybergamottin has been detected, but not quantified in, citrus. This could make 6',7'-dihydroxybergamottin a potential biomarker for the consumption of these foods. |
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CAS Number | 71339-34-9 |
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Structure | |
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Synonyms | Synonym | Source |
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4-[(6,7-Dihydroxy-3,7-dimethyl-2-octenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one | HMDB | Lepiochlorin | HMDB | 6,7-DHB | MeSH | 6',7'-Dihydroxybergamottin | MeSH | 6',7'-Dihydroxybergamottin (incorr.) | db_source |
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Predicted Properties | |
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Chemical Formula | C21H24O6 |
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IUPAC name | 4-{[(2Z)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one |
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InChI Identifier | InChI=1S/C21H24O6/c1-13(4-6-18(22)21(2,3)24)8-10-26-20-14-5-7-19(23)27-17(14)12-16-15(20)9-11-25-16/h5,7-9,11-12,18,22,24H,4,6,10H2,1-3H3/b13-8- |
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InChI Key | IXZUPBUEKFXTSD-JYRVWZFOSA-N |
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Isomeric SMILES | C\C(CCC(O)C(C)(C)O)=C\COC1=C2C=COC2=CC2=C1C=CC(=O)O2 |
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Average Molecular Weight | 372.417 |
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Monoisotopic Molecular Weight | 372.157288493 |
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Classification |
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Description | Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Coumarins and derivatives |
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Sub Class | Furanocoumarins |
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Direct Parent | Psoralens |
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Alternative Parents | |
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Substituents | - Psoralen
- Benzopyran
- 1-benzopyran
- Benzofuran
- Fatty alcohol
- Alkyl aryl ether
- Pyranone
- Fatty acyl
- Benzenoid
- Pyran
- Heteroaromatic compound
- Tertiary alcohol
- Furan
- 1,2-diol
- Secondary alcohol
- Lactone
- Oxacycle
- Ether
- Organoheterocyclic compound
- Organic oxygen compound
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Role | Biological role: |
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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 67.73%; H 6.50%; O 25.78% | DFC |
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Melting Point | Mp 104-106° | DFC |
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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 +12.7 (CHCl3) | DFC |
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Spectroscopic UV Data | Not Available | |
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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 | 4-[(6,7-Dihydroxy-3,7-dimethyl-2-octenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-9044000000-941ed62632b71a13305d | Spectrum | Predicted GC-MS | 4-[(6,7-Dihydroxy-3,7-dimethyl-2-octenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0kji-8894750000-911d6c503b24adefc3d3 | Spectrum |
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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 | splash10-05fr-0219000000-60828bda7a2eb1b2b838 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0zni-6898000000-9b3d898ebda6aef35d94 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ktr-9230000000-58a1d646ec73e9fb6806 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0fk9-0029000000-739b06d1a0a3b5242e1b | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0395000000-0b1e14b4c9f49fd15767 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-2920000000-580ae694ecab81deb640 | 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 | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB39066 |
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CRC / DFC (Dictionary of Food Compounds) ID | HBX86-S:LLQ09-Y |
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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 | 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 | |
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