4'-Hydroxyacetophenone | CAS:99-93-4 | Manufacturer ChemFaces

4'-Hydroxyacetophenone

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Description:

4'-Hydroxyacetophenone is a potent xanthine oxidase inhibitor, three 4′-hydroxyacetophenone-related phytoalexins from Polymnia sonchifolia have antifungal activity.

Targets:

Antifection | Xanthine oxidase

In vitro:

J Agric Food Chem. 2014 Apr 30;62(17):3742-9.

Inhibition of xanthine oxidase by Rhodiola crenulata extracts and their phytochemicals.[Pubmed: 24712453]

Using a fractionation technique, four phytochemicals were isolated from Rhodiola crenulata extracts. These compounds were identified as 4'-Hydroxyacetophenone (4-HAP), epicatechin-(4β,8)-epicatechin gallate (B2-3'-O-gallate), salidroside, and p-tyrosol using mass spectrometry and nuclear magnetic resonance spectroscopy.
METHODS AND RESULTS:
The inhibition of xanthine oxidase (XO) activity by these purified compounds was then evaluated and compared to that of a known XO inhibitor (allopurinol; IC50 = 12.21 ± 0.27 μM). Both 4'-Hydroxyacetophenone and B2-3'-O-gallate showed an XO inhibitory effect, for which the half maximal inhibitory concentration (IC50) values were 15.62 ± 1.19 and 24.24 ± 1.80 μM, respectively. However, salidroside and p-tyrosol did not show significant inhibitory effects on XO at 30 μM. Furthermore, an inhibition kinetics study indicated that 4'-Hydroxyacetophenone and B2-3'-O-gallate are mixed competitive inhibitors. The inhibition constants (Ki) of 4'-Hydroxyacetophenone and B2-3'-O-gallate were 8.41 ± 1.03 and 6.16 ± 1.56 μM, respectively.
CONCLUSIONS:
These results suggest that 4'-Hydroxyacetophenone and B2-3'-O-gallate are potent XO inhibitors.

4'-Hydroxyacetophenone Description

Source:	The herbs of Rhodiola crenulata
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

J Phys Chem A. 2014 Sep 18;118(37):8170-6.

Controlling dissociation of alkyl phenyl ketone radical cations in the strong-field regime through hydroxyl substitution position.[Pubmed: 24576102 ]

METHODS AND RESULTS:
The hydroxy-substituted alkyl phenyl ketones 2'-, 3'- and 4'- (ortho, meta, and para) hydroxyacetophenone were excited in the strong-field regime with wavelengths ranging from 1200-1500 nm to produce the respective radical cations. For 2'- and 3'-hydroxyacetophenone, the parent molecular ion dominated the mass spectrum, and the intensity of the fragment ions remained unchanged as a function of excitation wavelength. In contrast, 4'-Hydroxyacetophenone exhibited depletion of the parent molecular ion with corresponding enhanced formation of the benzoyl fragment ion upon excitation with 1370 nm as compared with other excitation wavelengths. Density functional (DFT) calculations suggest that dissociation occurs when the acetyl group in 4'-Hydroxyacetophenone radical cation twists out-of-plane with respect to the phenyl ring, enabling a one-photon transition between the ground cation state D0 and the excited cation state D2 to occur. The DFT calculations also suggest that the lack of dissociation in the wavelength-resolved strong-field excitation measurements for 2'- and 3'-hydroxyacetophenone arises because both isomers have a barrier to rotation about the carbon-carbon bond connecting the phenyl and acetyl groups.
CONCLUSIONS:
These results help elucidate the effects of substituents on the torsional motion of radical cations and illustrate the potential for controlling molecular dissociation through the addition of substituents.

Phytochemistry, 1996, 43(5):1019-21.

Three 4′-hydroxyacetophenone-related phytoalexins from Polymnia sonchifolia.[Reference: WebLink]

Inoculation of sliced yacon tubers with Pseudomonas cichorii resulted in the formation of antifungal compounds. Three major phytoalexins were isolated and identified by spectroscopic methods as 4′-hydroxy-3′-(3-methylbutanoyl)acetophenone, 4′-hydroxy-3′-(3-methyl-2-butenyl)acetophenone and 5-acetyl-2-(1-hydroxy-1-methylethyl)benzofuran.

Product Name	4'-Hydroxyacetophenone
Price:	$30 / 20mg
CAS No.:	99-93-4
Catalog No.:	CFN97575
Molecular Formula:	C₈H₈O₂
Molecular Weight:	136.2 g/mol
Purity:	>=98%
Type of Compound:	Phenols
Physical Desc.:	Powder
Source:	The herbs of Rhodiola crenulata
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Antifungal Compound Library Phytoalexin Compound Library Phenols Compound Library Antifection Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	7.3421 mL	36.7107 mL	73.4214 mL	146.8429 mL	183.5536 mL
5 mM	1.4684 mL	7.3421 mL	14.6843 mL	29.3686 mL	36.7107 mL
10 mM	0.7342 mL	3.6711 mL	7.3421 mL	14.6843 mL	18.3554 mL
50 mM	0.1468 mL	0.7342 mL	1.4684 mL	2.9369 mL	3.6711 mL
100 mM	0.0734 mL	0.3671 mL	0.7342 mL	1.4684 mL	1.8355 mL

CFN95530	Odontoside	20300-50-9	438.4	C₂₀H₂₂O₁₁
CFN95531	(3,4-Dihydroxyphenyl)methyl 3-(beta-D-glucopyranosyloxy)-4-hydroxybenzoate	877461-90-0	438.4	C₂₀H₂₂O₁₁
CFN95610	Protocatechuoylcalleryanin-3-O-beta-glucopyranoside	1263431-59-9	600.5	C₂₆H₃₂O₁₆
CFN95532	Caffeoylcalleryanin	20300-49-6	464.4	C₂₂H₂₄O₁₁
CFN98792	2-(4-Hydroxyphenyl)ethanol	501-94-0	138.2	C₈H₁₀O₂
CFN95623	4-(2-Hydroxyethyl)benzoic acid	46112-46-3	166.2	C₉H₁₀O₃
CFN99177	Salidroside	10338-51-9	300.30	C₁₄H₂₀O₇
CFN95367	Hydroxytyrosol 1-O-glucoside	76873-99-9	316.3	C₁₄H₂₀O₈
CFN95368	Cuneataside C	871720-16-0	448.4	C₁₉H₂₈O₁₂
CFN95775	4-Methoxy hydroxytyrosol 1-O-glucoside	N/A	330.3	C₁₅H₂₂O₈