CAS 6754-58-1 Xanthohumol - Analytical Products / Alfa Chemistry

CAT	APS6754581
CAS	6754-58-1
Structure
MDL Number	MFCD00210576
IUPAC Name	(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Molecular Weight	354.40
Molecular Formula	C21H22O5
Canonical SMILES	COc1cc(O)c(CC=C(C)C)c(O)c1C(=O)\C=C\c2ccc(O)cc2
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+
InChI Key	ORXQGKIUCDPEAJ-YRNVUSSQSA-N

Description	primary reference standard
Accurate Mass	354.1467
Format	Neat
Grade	primary reference standard
Size	10MG
Subcategory	Additional phytochemical reference materials

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Case Study

Development of Ammonia Sensors Based on Polylactic Acid Nanofibers Immobilized with Xanthohumol Extracts

Al-Senani, Ghadah M., and Salhah D. Al-Qahtani. Journal of Molecular Liquids 400 (2024): 124494.

Ammonia is an important industrial gaseous agent that is colorless. However, prolonged exposure to ammonia gas can lead to organ damage or even death. This study describes the use of environmentally friendly smart colorimetric polylactic acid nanofibers to prepare solid-state gas-phase colorimetric sensors for gaseous and aqueous ammonia.
Xanthohumol (XMOL) is a natural spectral probe found in the common hop (Humulus lupulus L.) plant. In the presence of a mordant (aluminum potassium sulfate), xanthohumol was directly fixed to polylactic acid nanofibers, synthesizing nanoparticles of the mordant/xanthohumol (M/XMOL) (M/XMOL) coordination complex. The small molecular size and high water solubility of xanthohumol (M/XMOL) make it a suitable sensor for gaseous and aqueous ammonia. The color change of the xanthohumol-modified polylactic acid nanofibers from yellow to colorless upon exposure to ammonia water was examined using CIE Lab color parameters and absorbance spectra. This change can be attributed to the intramolecular charge transfer caused by the switching of Xanthohumol molecules. Within fractions of a second, the polylactic acid nanofiber fabric displayed a colorimetric change, with a detection limit of 10-450 mg/L. The absorption spectrum of the xanthohumol probe exhibited a blue shift in the ammonia water solution, with the wavelength changing from 465 nm to 315 nm (with an isosbestic point at 370 nm).

Preparation of Xanthohumol and Chitosan-Oxidized Starch Composite Films

Yang, Fan, et al. Food Packaging and Shelf Life 45 (2024): 101326.

Foodborne pathogens remain a major culprit in food spoilage and illness, making the use of natural polymer biomaterials combined with natural bioactive compounds for food packaging research a new development trend. This study for the first time combines the xanthohumol (XN), a chalcone active compound with potential for inexpensive sourcing, with chitosan/oxidized starch films (CS/OS) to develop a novel multifunctional chitosan/oxidized starch/Xanthohumol (CS/OS/XN) packaging film.
Preparation of CS/OS/XN Films: Chitosan (CS) was dissolved in a 1% acetic acid solution (v/v), and after ultrasonic treatment, a 3% (w/v) CS solution was obtained. This CS solution was then mixed with a 6% (w/v) oxidized starch (OS) solution (completely gelatinized at 80 °C) in a mass ratio of 1:1. Xanthohumol (XN) was added at mass fractions of 0.05% (COXF-1), 0.1% (COXF-2), 0.25% (COXF-3), 0.5% (COXF-4), and 1% (COXF-5). Glycerol, accounting for 6% of the total mass of the mixed system, was then added. After thorough mixing, the solution was poured onto the surface of a polytetrafluoroethylene plate (100×100×5 mm) using the casting method, while a control OS/CS film (COF) was also prepared. After forming at room temperature, the films were placed in a constant temperature and humidity incubator and stored for 48 hours at 25 °C and 55% humidity before use.

Xanthohumol Inhibits Cell Proliferation and Induces Apoptosis in Human Thyroid Cells

Carvalho, Daniel O., et al. Food and Chemical Toxicology 121 (2018): 450-457.

This study reports on the cell growth inhibitory potential of xanthohumol (XN) against human papillary thyroid carcinoma cells. xanthohumol is a natural isoprenoid flavonoid found in hops and beer.
The research demonstrates that XN reduces the proliferation of TPC-1 cancer cells in a dose- and time-dependent manner. At low concentrations (10 μM), XN significantly inhibits carcinogenic effects by halting or slowing down cell division, thereby maintaining cell viability. At higher concentrations (100 μM), a decrease in cell viability was observed due to the induction of apoptosis. It was shown that XN induces DNA fragmentation in TPC-1 cells and promotes cell cycle arrest, resulting in a reduced percentage of cells in the G1 phase and an increased percentage of cells in the S phase after 72 hours of treatment.
Moreover, XN exposure triggered an increase in the activities of caspase-3 and caspase-7, supporting its role in the activation of apoptosis. Cell-free studies indicate that high concentrations of XN lead to an increase in free radicals generated by the Fenton system, which may mediate apoptosis through pro-oxidative pathways. In conclusion, the study data show that XN induces apoptosis in TPC-1 cancer cells in a concentration-dependent manner, suggesting that XN is a promising candidate for thyroid cancer treatment.