| Identification | Back Directory | [Name]
xanthoangelol | [CAS]
62949-76-2 | [Synonyms]
xanthoangelol
(E)-1-[3-[(E)-3,7-Dimethyl-2,6-octadienyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
2-Propen-1-one, 1-[3-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)-, (2E)- | [Molecular Formula]
C25H28O4 | [MDL Number]
MFCD17167046 | [MOL File]
62949-76-2.mol | [Molecular Weight]
392.49 |
| Chemical Properties | Back Directory | [Melting point ]
141-143 °C | [Boiling point ]
605.8±55.0 °C(Predicted) | [density ]
1.165±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [form ]
Solid | [pka]
7.57±0.50(Predicted) | [color ]
Light yellow to yellow | [InChI]
InChI=1S/C25H28O4/c1-17(2)5-4-6-18(3)7-13-21-24(28)16-14-22(25(21)29)23(27)15-10-19-8-11-20(26)12-9-19/h5,7-12,14-16,26,28-29H,4,6,13H2,1-3H3/b15-10+,18-7+ | [InChIKey]
LRSMBOSQWGHYCW-MDGZPELGSA-N | [SMILES]
C(C1=CC=C(O)C(C/C=C(\C)/CC/C=C(/C)\C)=C1O)(=O)/C=C/C1=CC=C(O)C=C1 | [LogP]
7.240 (est) |
| Hazard Information | Back Directory | [Uses]
Xanthoangelol, extracted from Angelica keiskei, suppresses obesity-induced inflammatory responses. Xanthoangelol possesses antibacterial activity. Xanthoangelol inhibits monoamine oxidases. Xanthoangelol induces apoptosis in neuroblastoma and leukemia cells[1][2][3][4]. | [in vivo]
Xanthoangelol (0.1% or 0.15% w/w, mixed in a high-fat diet, daily for 14 weeks) suppresses inflammatory mediators in WAT of diet-induced obese mice[1].
| Animal Model: | High-fat diet-induced obese (DIO) mice[1] | | Dosage: | 0.1% or 0.15% w/w | | Administration: | mixed in a high-fat diet, daily for 14 weeks | | Result: | Showed fewer positively stained macrophages, suppressed the gene expression of inflammatory marker MCP-1 and TNF-a, increased oxygen consumption in DIO mice. |
| [storage]
Store at -20°C | [References]
[1] Li Y, et al. Xanthoangelol and 4-hydroxyderrcin suppress obesity-induced inflammatory responses. Obesity (Silver Spring). 2016 Nov;24(11):2351-2360. DOI:10.1002/oby.21611
[2] Inamori Y, et al. Antibacterial activity of two chalcones, xanthoangelol and 4-hydroxyderricin, isolated from the root of Angelica keiskei KOIDZUMI. Chem Pharm Bull (Tokyo). 1991 Jun;39(6):1604-5. DOI:10.1248/cpb.39.1604
[3] Kim JH, et al. Xanthoangelol and 4-Hydroxyderricin Are the Major Active Principles of the Inhibitory Activities against Monoamine Oxidases on Angelica keiskei K. Biomol Ther (Seoul). 2013 May 30;21(3):234-40. DOI:10.4062/biomolther.2012.100
[4] Keiichi TABATA, et al. Xanthoangelol, a Major Chalcone Constituent of Angelica keiskei, Induces Apoptosis in Neuroblastoma and Leukemia Cells. Biol. Pharm. Bull. 28(8) 1404-1407 (2005). |
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