Specifications
- Purity
- ≥98% (NMR)
- Appearance
- Yellow powder
- Identity
- 1H-NMR
Properties
- Solvents
- DMSO (10 mg/ml), ethanol (10 mg/ml)
- Melting Point
- 158 - 163°C
- UV / Vis
- 348, 368 nm (lit.)
Category: Phytochemicals
Xanthohumol is a cell-permeable natural prenylated chalcone isolated from the hop plant, H. lupulus. Xanthohumol and its metabolites induce protective detoxification enzymes, at least in part via the nuclear factor erythroid-2-related factor 2 pathway. Xanthohumol can have anti-inflammatory, antioxidant, anticarcinogenic, antidiabetic and osteogenic effects. Xanthohumol binds to the N-terminal domain of p97 ATPase (VCP, valosin-containing protein), an essential protein for autophagosome maturation. Xanthohumol inhibits the function of p97 ATPase thereby impairing autophagosome maturation and resulting in accumulation of the microtubule-associated protein 1 light chain 3-II (LC3-II)1. Xanthohumol inhibits diacylglycerol acetyltransferase (DGAT) and human P450 enzymes. It also inhibits the expression of HIF-1α and VEGF under hypoxic conditions.
Synonyms | 2',4,4'-Trihydroxy-6'-methoxy-3'-prenylchalcone |
---|---|
Purity | ≥98% (NMR) |
Appearance | Yellow powder |
CAS-Number | 6754-58-1 |
Molecular Formula | C21H22O5 |
Molecular Weight | 354.40 |
Identity | 1H-NMR |
Solvents | DMSO (10 mg/ml), ethanol (10 mg/ml) |
Melting Point | 158 – 163°C |
UV / Vis | 348, 368 nm (lit.) |
Smiles | OC1=C(C(/C=C/C2=CC=C(O)C=C2)=O)C(OC)=CC(O)=C1C/C=C(C)/C |
InChi Key | ORXQGKIUCDPEAJ-YRNVUSSQSA-N |
Shipping | AMBIENT |
Short Term Storage | +4°C |
Long Term Storage | +4°C |
Handling Advice | Protect from light and moisture. |
Use / Stability | Stable for at least 2 years after receipt when stored at +4°C. |
Hazard statements | H317-H400 |
Precautionary statements | P273-P280 |
GHS Symbol | GHS07+GHS09 |
Signal word | Warning |
RIDADR | UN3077 |
Transportation | Packing Group III |
References | (1) N. Tabata, et al., Phytochemistry 46, 683 (1997), (2) J.F. Stevens & J.E. Page, Phytochemistry 65, 1317 (2004) (Review), (3) C. Gerhauser, Mol. Nutr. Food Res. 49, 827 (2005) (Review), (4) P.J. Magalhaes, et al., Nat. Prod. Commun. 4, 591 (2009) (Review), (5) J. Inokoshi, et al., J. Antibiot. 62, 51 (2009), (7) R. Vene, et al., Mol. Med. 18, 1292 (2012), (8) Y. Sasazawa, et al., ACS Chem. Biol. 7, 892 (2012), (9) V. Krajka-Kuzniak, et al., Toxicol. In Vitro 27, 149 (2013), (10) R. Costa, et al., J. Nat. Prod. 76, 2047 (2013), (11) T. Schilling, et al., J. Ster. Biochem. Mol. Biol. 139, 252 (2014), (12) M. Liu, et al., Molecules 20, 754 (2015) (Review), (13) C.H. Jiang, et al., Front. Pharmacol. 9, 530 (2018) (Review) |
InChi | InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+ |
Quantity | 25 mg, 50 mg, Bulk |