4-(4-Hydroxyphenyl)-2-butanone | CAS:5471-51-2

4-(4-Hydroxyphenyl)-2-butanone

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Description:

4-(4-Hydroxyphenyl)-2-butanone(Raspberry ketone,RK) is widely used as a fragrance in cosmetics and as a flavoring agent in foodstuff, it also shows PPAR-α agonistic activity. It is cytotoxic to melanocytes through the binding of RK-derived quinones to thiol proteins and the pro-oxidant activity of the RK-oligomer, the exposure of human skin to RK can cause chemical/occupational leukoderma.

Targets:

Tyrosinase

In vitro:

Chem Res Toxicol. 2017 Mar 20;30(3):859-868.

Tyrosinase-Catalyzed Oxidation of the Leukoderma-Inducing Agent Raspberry Ketone Produces (E)-4-(3-Oxo-1-butenyl)-1,2-benzoquinone: Implications for Melanocyte Toxicity.[Pubmed: 28219012]

The exposure of human skin to 4-(4-Hydroxyphenyl)-2-butanone (raspberry ketone, RK) is known to cause chemical/occupational leukoderma. RK has a structure closely related to 4-(4-hydroxyphenyl)-2-butanol (rhododendrol), a skin whitening agent that was found to cause leukoderma in the skin of consumers in 2013. Rhododendrol is a good substrate for tyrosinase and causes a tyrosinase-dependent cytotoxicity to melanocytes, cells that are responsible for skin pigmentation.
METHODS AND RESULTS:
Therefore, it is expected that RK exerts its cytotoxicity to melanocytes through the tyrosinase-catalyzed oxidation to cytotoxic o-quinones. The results of this study demonstrate that the oxidation of RK by mushroom tyrosinase rapidly produces 4-(3-oxobutyl)-1,2-benzoquinone (RK-quinone), which is converted within 10-20 min to (E)-4-(3-oxo-1-butenyl)-1,2-benzoquinone (DBL-quinone). These quinones were identified as their corresponding catechols after reduction by ascorbic acid. RK-quinone and DBL-quinone quantitatively bind to the small thiol N-acetyl-l-cysteine to form thiol adducts and can also bind to the thiol protein bovine serum albumin through its cysteinyl residue. DBL-quinone is more reactive than RK-quinone, as judged by their half-lives (6.2 min vs 10.5 min, respectively), and decays rapidly to form an oligomeric pigment (RK-oligomer). The RK-oligomer can oxidize GSH to GSSG with a concomitant production of hydrogen peroxide, indicating its pro-oxidant activity, similar to that of the RD-oligomer.
CONCLUSIONS:
These results suggest that RK is cytotoxic to melanocytes through the binding of RK-derived quinones to thiol proteins and the pro-oxidant activity of the RK-oligomer.

In vivo:

Regul Toxicol Pharmacol. 2015 Oct;73(1):196-200.

Raspberry ketone in food supplements--High intake, few toxicity data--A cause for safety concern?[Pubmed: 26160596]

Raspberry ketone (4-(4-Hydroxyphenyl)-2-butanone) is marketed on the Internet as a food supplement. The recommended intake is between 100 and 1400 mg per day. The substance is naturally occurring in raspberries (up to 4.3 mg/kg) and is used as a flavouring substance.
METHODS AND RESULTS:
Toxicological studies on raspberry ketone are limited to acute and subchronic studies in rats. When the lowest recommended daily dose of raspberry ketone (100 mg) as a food supplement is consumed, it is 56 times the established threshold of toxicological concern (TTC) of 1800 μg/day for Class 1 substances. The margin of safety (MOS) based on a NOAEL of 280 mg/kg bw/day for lower weight gain in rats is 165 at 100 mg and 12 at 1400 mg. The recommended doses are a concern taking into account the TTC and MOS.
CONCLUSIONS:
Investigations of raspberry ketone in quantitative structure-activity relationship (QSAR) models indicated potential cardiotoxic effects and potential effects on reproduction/development. Taking into account the high intake via supplements, the compound's toxic potential should be clarified with further experimental studies. In UK the pure compound is regarded as novel food requiring authorisation prior to marketing but raspberry ketone is not withdrawn from Internet sites from this country.

4-(4-Hydroxyphenyl)-2-butanone Description

Source:	The rhizomes of Zingber officinale Rosc.
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.

Product Name	4-(4-Hydroxyphenyl)-2-butanone
Price:	$30 / 20mg
CAS No.:	5471-51-2
Catalog No.:	CFN90894
Molecular Formula:	C₁₀H₁₂O₂
Molecular Weight:	164.2 g/mol
Purity:	>=98%
Type of Compound:	Phenols
Physical Desc.:	Powder
Source:	The rhizomes of Zingber officinale Rosc.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS
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	Toxicity Compound Library Dietary supplement Compound Library Pro-oxidants Compound Library Phenols Compound Library Tyrosinase Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	6.0901 mL	30.4507 mL	60.9013 mL	121.8027 mL	152.2533 mL
5 mM	1.218 mL	6.0901 mL	12.1803 mL	24.3605 mL	30.4507 mL
10 mM	0.609 mL	3.0451 mL	6.0901 mL	12.1803 mL	15.2253 mL
50 mM	0.1218 mL	0.609 mL	1.218 mL	2.4361 mL	3.0451 mL
100 mM	0.0609 mL	0.3045 mL	0.609 mL	1.218 mL	1.5225 mL

CFN99465	Cimidahurinine	142542-89-0	316.3	C₁₄H₂₀O₈
CFN98355	3,4-Dihydroxyphenylglycol	28822-73-3	170.2	C₈H₁₀O₄
CFN98979	4-(2-Hydroxy-1-methoxyethyl)-1,2-benzenediol	577976-26-2	184.2	C₉H₁₂O₄
CFN99763	Homovanillic acid	306-08-1	182.17	C₉H₁₀O₄
CFN93104	4-Phenylbutan-2-one	2550-26-7	148.2	C₁₀H₁₂O
CFN93101	trans-4-phenylbut-3-en-2-one	1896-62-4	146.2	C₁₀H₁₀O
CFN93103	1-Phenylbutane-1,3-dione	93-91-4	162.2	C₁₀H₁₀O₂
CFN95785	Plumbagic acid	75640-06-1	224.2	C₁₁H₁₂O₅
CFN90894	4-(4-Hydroxyphenyl)-2-butanone	5471-51-2	164.2	C₁₀H₁₂O₂
CFN99702	Zingerone	122-48-5	194.23	C₁₁H₁₄O₃