| Identification | Back Directory | [Name]
(E)-1,7-BIS(4-HYDROXY-3-METHOXYPHENYL)HEPT-4-EN-3-ONE | [CAS]
128700-97-0 | [Synonyms]
GINGERENONE A
(E)-1,7-Bis(3-methoxy-4-hydroxyphenyl)-4-hepten-3-one
(E)-1,7-BIS(4-HYDROXY-3-METHOXYPHENYL)HEPT-4-EN-3-ONE
4-Hepten-3-one, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (4E)- | [Molecular Formula]
C21H24O5 | [MDL Number]
MFCD06656136 | [MOL File]
128700-97-0.mol | [Molecular Weight]
356.41 |
| Chemical Properties | Back Directory | [Boiling point ]
571.3±50.0 °C(Predicted) | [density ]
1.183±0.06 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
Chloroform (Slightly), Ethanol (Slightly) | [form ]
Oil | [pka]
10.01±0.20(Predicted) | [color ]
Light Yellow to Yellow | [InChI]
InChI=1S/C21H24O5/c1-25-20-13-15(8-11-18(20)23)5-3-4-6-17(22)10-7-16-9-12-19(24)21(14-16)26-2/h4,6,8-9,11-14,23-24H,3,5,7,10H2,1-2H3/b6-4+ | [InChIKey]
FWDXZNKYDTXGOT-GQCTYLIASA-N | [SMILES]
C(C1=CC=C(O)C(OC)=C1)CC(=O)/C=C/CCC1=CC=C(O)C(OC)=C1 |
| Hazard Information | Back Directory | [Uses]
Gingerenone A is an antifungal and antiparasitic diarylheptenone that is isolated from Zingiber officinale (more commonly known as ginger), a medicinal plant that is used to treat inflammation and musculoskeletal disorders. | [Definition]
ChEBI: Gingerenone A is a diarylheptanoid. | [Biological Activity]
Gingerenone A is a potent anticancer agent isolated from Ginger (Zingiber officinale) th at exhibits minimal toxicity toward normal cells. Gingerenone A potently inhibits JAK2 (Janus Kinase 2) and S6K1 (p70 ribosomal S6 kinase). Gingerenone A significantly suppressed tumor growth in vivo. Alsoit exhibits promising senolytic properties. Gingerenone A selectively eliminate senescent cells in WI-38 human fibroblasts rendered senescent by exposure to ionizing radiation. | [in vivo]
Gingerenone A (10-50 mg/kg, orally, once a day, 15 weeks) reduces the increase in fat mass induced by a high-fat diet in mice by decreasing the size of fat cells, thereby inhibiting obesity and inflammation in adipose tissue[2].
Gingerenone A (5-20 mg/kg, orally, once a day, 7 days) can alleviate ferroptosis in the SLI of DSS-induced colitis mice, and its protective effect is associated with the activation of the Nrf2-Gpx4 signaling pathway[4]. | Animal Model: | HFD mice[2] | | Dosage: | 10, 50 mg/kg; daily; 15 weeks | | Administration: | Oral | | Result: | Reduced fat gain without significantly affecting caloric intake, reduced visceral fat mass, and made fat cells smaller. |
| Animal Model: | Mice induced by DSS[6] | | Dosage: | 5, 20 mg/kg; daily; 7 days | | Administration: | Oral | | Result: | Alleviated DSS-induced liver pathological damage, liver parameters and cytokine levels, increased antioxidant enzyme activities, alleviated ferroptosis, upregulated GPX4 expression, and activated Nrf2. |
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