Identifikatoren & physikalische Daten
| CAS No. | 482-46-2 |
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| Summenformel | C21H22O4 |
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| Durchschnittliche Molmasse | 338,4 g/mol |
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| Monoisotopische Masse | 338,15180918 g/mol |
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| SMILES | CC(C)=CCC/C(C)=C/COc1c2ccoc2cc2oc(=O)ccc12 |
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| InChIKey | DBMJZOMNXBSRED-OQLLNIDSSA-N |
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| PubChem CID | 5471349 |
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| ChEMBL | CHEMBL1078442 |
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| ChEBI | CHEBI:70476 |
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| EC No. | 639-137-1 |
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| DTXSID | DTXSID50897528 |
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Chemische & physikalische Eigenschaften
| XLogP | 5,6 |
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| Polarare Oberfläche (TPSA) | 48,7 |
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| H-Brücken-Donoren | 0 |
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| H-Brücken-Akzeptoren | 4 |
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| Frei drehbare Bindungen | 6 |
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| Schwere Atome | 25 |
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| Formalladung | 0 |
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| Komplexität | 570 |
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| Lipide | Polyketides [PK] -> Flavonoids [PK12] -> Other Flavonoids [PK1216] |
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| SpringerMaterials Properties | Chemical shift |
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Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 2.2% (2 of 92) of reports.WarningH317 (97.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 92 reports by companies from 2 notifications to the ECHA C&L Inventory.Not Classified |
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| Hazard Classes and Categories | Skin Sens. 1 (97.8%)Not Classified |
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| Gesundheitliche Auswirkungen | The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (L135). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (A15105). The SKLM regards the additional risk of skin cancer arising from the consumption of typical quantities of furocoumarin-containing foods, which remain significantly below the range of phototoxic doses, as insignificant. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions. (L2157) Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs. |
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| Toxizitätsübersicht | Bergamottin is a potent chemopreventive agent against aflatoxin B1-inducible cyotoxicity in H4IIE cells with a bifunctional effects on glutathione S-transferase and CYP1A. Potent inhibitor and inactivator of cytochrome P450 1A1-mediated monooxygenase in both murine hepatic microsomes and in a reconstituted system using purified human P450 1A1 (L579). The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. (L579) |
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