4-(4-Hydroxyphenyl)-2-butanone

Names

[ Name ]:
4-(4-Hydroxyphenyl)-2-butanone

[Synonym ]:
Oxyphenalon
4-hydroxy benzyl acetone
Raspberry keton
4-(4-Hydroxyphenyl)-2-butanone
Frambinone
Rheosmin
OXYPHENONE
OXYPHENYLON
Raspberry ketone
EINECS 226-806-4
RASBERRY KETONE
MFCD00002394
p-Hydroxy benzylacetone
FEMA 2588
OXANONE

Biological Activity

[Description]:

Raspberry ketone is a major aromatic compound of red raspberry, widely used as a fragrance in cosmetics and as a flavoring agent in foodstuff; also shows PPAR-α agonistic activity.

[Related Catalog]:

Research Areas >> Metabolic Disease

Natural Products >> Phenols

Research Areas >> Cardiovascular Disease

[Target]

PPAR-α

[In Vitro]

Raspberry ketone (1, 10, 20, and 50 μM) suppresses adipogenesis and lipid accumulation in 3T3-L1 pre-adipocytes. Raspberry ketone (10 µM) significantly blocks C/EBPα, PPARγ, and aP2 expression and increases the expression of ATGL and HSL, and CPT1B[1].

[In Vivo]

Raspberry ketone (0.5%, 1%, or 2%) increasses the levels of total cholesterol (TC), triglycerides (TG), low-density lipoprotein cholesterol contents (LDL-C), ISI (insulin-sensitivr index), PPAR-α and LDLR, decreases the serum levels of AST (aspartate aminotransferase), ALT (alanine aminotransferase), ALP (alkaline phosphatase), IRI (insulin resistance index), GLU (glucose), INS (insulin-sensitivr index), LEP (leptin), and TNF-α in rats compared with a high-fat diet-induced NASH model. Raspberry ketone also causes increased SOD activities[2]. Raspberry ketone shows cardioprotective action against isoproterenol-induced myocardial infarction in rats, and the effects may be due to its PPAR-α agonistic activity[3].

[Cell Assay]

For the cytotoxicity study, 3T3-L1 pre-adipocytes are cultured and differentiated. After Raspberry ketone treatment for 4 d in DMEM containing 10% fetal bovine serum, the lactate dehydrogenase (LDH) concentration in the medium is immediately detected with the CytoTox 96 nonradioactive cytotoxicity assay kit[1].

[Animal admin]

During the experimental period, the animal room holds four rats per cage, with free access to water and food, under conditions of temperature controlled at 20-26°C, humidity at 40-70%, and a 12/12-h day-night light cycle. Rats are fed with normal diet for 1 week and then randomly divided into five groups: normal control (NC) group (n=8) fed normal diet for 8 weeks, the model control (MC) group (n=8) fed high-fat diet (82% standard diet, 8.3% yolk powder, 9.0% lard, 0.5% cholesterol, and 0.2% sodium taurocholate), the Raspberry ketone low-dose (RKL) group (n=8), the Raspberry ketone middle-dose (RKM) group (n=8), and the Raspberry ketone high-dose (RKH) group (n=8). Rats are first fed with high-fat diet for 4 weeks, and then these rats are given intragastrically 0.5%, 1%, or 2% Raspberry ketone. The first two groups of rats are intragastrically administered salad oil at the same dose (2 mL/day per rat) once a day at 10:00 a.m., lasting for 4 weeks[2].

[References]

[1]. Park KS. Raspberry ketone, a naturally occurring phenolic compound, inhibits adipogenic and lipogenic gene expression in 3T3-L1 adipocytes. Pharm Biol. 2015 Jun;53(6):870-5.

[2]. Wang L, et al. Raspberry ketone protects rats fed high-fat diets against nonalcoholic steatohepatitis. J Med Food. 2012 May;15(5):495-503.

[3]. Khan V, et al. Raspberry ketone protects against isoproterenol-induced myocardial infarction in rats. Life Sci. 2018 Feb 1;194:205-212.

[Related Small Molecules]

GW9662 | Retinoic acid | Elafibranor | GW501516 | Troglitazone | T0070907 | Pemafibrate | CDDO-Im | Wy-14643 | GW0742 | GW1929 | FH535 | Icariin | Daidzein | Fisetin

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
292.2±15.0 °C at 760 mmHg

[ Melting Point ]:
81-85 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₂O₂

[ Molecular Weight ]:
164.201

[ Flash Point ]:
122.9±13.0 °C

[ Exact Mass ]:
164.083725

[ PSA ]:
37.30000

[ LogP ]:
0.94

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.535

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EL8925000

CHEMICAL NAME :: 2-Butanone, 4-(p-hydroxyphenyl)-

CAS REGISTRY NUMBER :: 5471-51-2

BEILSTEIN REFERENCE NO. :: 0776080

LAST UPDATED :: 199701

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C10-H12-O2

MOLECULAR WEIGHT :: 164.22

WISWESSER LINE NOTATION :: QR D2V1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1320 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - analgesia

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 8,349,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 350 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - analgesia

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 8,349,1970 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - M4912 No. of Facilities: 18 (estimated) No. of Industries: 1 No. of Occupations: 13 No. of Employees: 3245 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - M4912 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 1557 (estimated) No. of Female Employees: 276 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S26-S36/37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
EL8925000

[ HS Code ]:
2914501100

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914501100

[ Summary ]:
HS: 2914501100. 4-(4-hydroxyphenyl)butan-2-one. VAT:17.0%. tax rebate rate:9.0%. supervision conditions:None. MFN tarrif:5.5%. general tariff:30.0%

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