Xanthohumol
| Code | Size | Price |
|---|
| CDX-X0005-M025 | 25 mg | £280.00 |
Quantity:
| CDX-X0005-M050 | 50 mg | £437.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Host Type: Plant
Regulatory Status: RUO
Shipping:
AMBIENT
Storage:
+4°C
Documents
Further Information
Alternate Names/Synonyms:
2',4,4'-Trihydroxy-6'-methoxy-3'-prenylchalcone
Appearance:
Yellow powder.
CAS:
6754-58-1
Class:
9
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07,GHS09
Handling Advice:
Protect from light and moisture.
Hazards:
H317-H400
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+
InChiKey:
ORXQGKIUCDPEAJ-YRNVUSSQSA-N
Long Description:
Chemical. CAS: 6754-58-1. Formula: C21H22O5. MW: 354.40. 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-1alpha and VEGF under hypoxic conditions.
MDL:
MFCD00210576
Molecular Formula:
C21H22O5
Molecular Weight:
354.4
Package Type:
Vial
PG:
III
Precautions:
P273-P280
Product Description:
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-1alpha and VEGF under hypoxic conditions.
Purity:
>98% (NMR)
Signal word:
Warning
SMILES:
OC1=C(C(/C=C/C2=CC=C(O)C=C2)=O)C(OC)=CC(O)=C1C/C=C(C)/C
Solubility Chemicals:
Soluble in DMSO (10mg/ml) or ethanol (10mg/ml).
Source / Host:
Plant
Transportation:
Non-hazardous
UN Nummer:
3077
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at +4°C.
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)