Benzylacetone

Names

[ Name ]:
Benzylacetone

[Synonym ]:
Phenethyl methyl ketone
4-Phenyl-2-butanone
Methyl phenylethyl ketone
Benzyl acetone
4-Penylbutan-2-one
Methyl 2-phenylethyl ketone
4-phenylbutan-2-one
2-Butanone,4-phenyl
β-Phenylethyl methyl ketone
EINECS 219-847-4
1-Phenyl-3-butanone
2-Butanone, 4-phenyl-
Methyl phenethyl ketone
Benzylacetone
MFCD00008790
UNII-UZM5QH16YW

Biological Activity

[Description]:

Benzylacetone is an aromatic compound from agarwood[1]. Benzylacetone exhibits potent and reversible antityrosinase (mushroom) activity， with IC50s of 2.8 mM and 0.6 mM for monophenolase and diphenolase, respectively[2]. Benzylacetone has appetite-enhancing and locomotor-reducing effects[3].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Tyrosinase

Research Areas >> Metabolic Disease

[Target]

IC50: 2.8 mM (monophenolase, tyrosinase mushroom), 0.6 mM (diphenolase, tyrosinase mushroom)[2]

[References]

[1]. Takamatsu S, et al. Agarotetrol: a source compound for low molecular weight aromatic compounds from agarwood heating. J Nat Med. 2018 Mar;72(2):537-541.

[2]. Liu X, et al. Inhibition effects of benzylideneacetone, benzylacetone, and 4-phenyl-2-butanol on the activity of mushroom tyrosinase. J Biosci Bioeng. 2015 Mar;119(3):275-9.

[3]. Ogawa K, et al. Appetite-Enhancing Effects: The Influence of Concentrations of Benzylacetone and trans-Cinnamaldehyde and Their Inhalation Time, as Well as the Effect of Aroma, on Body Weight in Mice. Biol Pharm Bull. 2016;39(5):794-8.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
233.5±0.0 °C at 760 mmHg

[ Melting Point ]:
-13ºC

[ Molecular Formula ]:
C₁₀H₁₂O

[ Molecular Weight ]:
148.202

[ Flash Point ]:
98.3±0.0 °C

[ Exact Mass ]:
148.088821

[ PSA ]:
17.07000

[ LogP ]:
1.67

[ Vapour Pressure ]:
0.1±0.4 mmHg at 25°C

[ Index of Refraction ]:
1.504

[ Water Solubility ]:
PRACTICALLY INSOLUBLE

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EL9600000

CHEMICAL NAME :: 2-Butanone, 4-phenyl-

CAS REGISTRY NUMBER :: 2550-26-7

BEILSTEIN REFERENCE NO. :: 1907123

LAST UPDATED :: 199701

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C10-H12-O

MOLECULAR WEIGHT :: 148.22

WISWESSER LINE NOTATION :: 1V2R

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 21,647,1983

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 21,647,1983 ** ACUTE TOXICITY DATA **

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 21,647,1983

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1590 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 15(5),7,1980

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 583 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 15(5),7,1980

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 21,647,1983

Safety Information

[ Personal Protective Equipment ]:
Faceshields;full-face respirator (US);Gloves;Goggles;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R38

[ Safety Phrases ]:
S37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
1

[ RTECS ]:
EL9600000

[ HS Code ]:
29143900

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914399090

[ Summary ]:
2914399090. other aromatic ketones without other oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

Articles

Online capillary solid-phase microextraction coupled liquid chromatography-mass spectrometry for analysis of chiral secondary alcohol products in yeast catalyzed stereoselective reduction cell culture.

J. Chromatogr. A. 1380 , 1-10, (2015)

An online solid-phase microextraction coupled liquid chromatography-electrospray ionization-ion trap mass spectrometry was developed for the analysis of trace R- and S-4-phenyl-2-butanol (R- and S-pbo...

Structure-activity relationship of cinnamaldehyde analogs as inhibitors of AI-2 based quorum sensing and their effect on virulence of Vibrio spp.

PLoS ONE 6(1) , e16084, (2011)

Many bacteria, including Vibrio spp., regulate virulence gene expression in a cell-density dependent way through a communication process termed quorum sensing (QS). Hence, interfering with QS could be...