| Identification | Back Directory | [Name]
heraclenin | [CAS]
2880-49-1 | [Synonyms]
heraclenin
HERACLENIN (P)
9-[[3,3-dimethyloxiran-2-yl]methoxy]furo[3,2-g]chromen-7-one
7H-Furo[3,2-g][1]benzopyran-7-one, 9-[[(2R)-3,3-dimethyl-2-oxiranyl]methoxy]- | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C16H14O5 | [MDL Number]
MFCD01725710 | [MOL File]
2880-49-1.mol | [Molecular Weight]
286.28 |
| Chemical Properties | Back Directory | [Melting point ]
111℃ | [Boiling point ]
471.4±45.0 °C(Predicted) | [density ]
1.320±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [color ]
White to off-white | [LogP]
1.680 (est) |
| Hazard Information | Back Directory | [Description]
Heraclenin is a member of the class of compounds known as psoralens. Psoralens 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. Heraclenin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Heraclenin can be found in carrot, lemon, and wild carrot, which makes heraclenin a potential biomarker for the consumption of these food products. | [Uses]
Heraclenin inhibits T cell-receptor-mediated proliferation in human primary T cells in a concentration-dependent manner. Heraclenin also induces apoptosis. While imperatorin induces DNA fragmentation at the G1/S phase of the cell cycle, heraclenin induces DNA fragmentation at the G2/M phases of the cell cycle, thus despite a close structural similarity they induce apoptosis in mechanistically different ways. | [Biological Functions]
Heraclenin has anticoagulant, and anti-inflammatory activities, it also has mutagenicity in Chlamydomonas reinhardii. Heraclenin can induce apoptosis in Jurkat leukemia cells, it has a strong clastogenic effect . (+)-Heraclenin displays significant levels of antiplasmodial and moderate levels of antimicrobial activities. | [Biological Activity]
Heraclenin, a natural furanocoumarin, significantly inhibits T cell receptor-mediated proliferation in human primary T cells in a concentration-dependent manner by targeting nuclear factor of activated T-cells (NFAT). | [in vitro]
Heraclenin, a furocoumarin with an epoxide group in its side chain, was analyzed to see if it induced structural chromosome aberrations and sister-chromatid exchanges (SCEs) in human lymphocytes in vitro. The results were compared directly with those of imperatorin, which differs from Heraclenin only in lacking an epoxide group. An equally strong clastogenic effect was found for both Heraclenin and imperatorin: the number of metaphases with breaks was increased in both cases by approximately a factor of 6. Heraclenin produced a considerable dose-dependent increase in the SCE rate, i.e., by about 60 induced SCEs/metaphase, whereas imperatorin induced only about 4 SCEs/metaphase. | [target]
Immunology & Inflammation related | Antifection |
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