1,3-Diphenylpropane-1,3-dione

Names

[ CAS No. ]:
120-46-7

[ Name ]:
1,3-Diphenylpropane-1,3-dione

[Synonym ]:
1,3-Diphenyl-1,3-propanedione
1,3-diphenylpropane-1,3-dione
Dibenzoylmethane
MFCD00003085
phenacyl phenyl ketone
EINECS 204-398-9
1,3-Propanedione, 1,3-diphenyl-

Biological Activity

[Description]:

Dibenzoylmethane, a minor ingredient in licorice, activates Nrf2 and prevents various cancers and oxidative damage. Dibenzoylmethane, an analog of curcumin, results in dissociation from Keap1 and nuclear translocation of Nrf2[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> NF-κB >> Keap1-Nrf2

Research Areas >> Metabolic Disease

[In Vitro]

Dibenzoylmethane (10, 20, 30, 40, 50 μM; 6 hours) treatment concentration-dependently increases the mRNA level of HO-1 but has no effect on the mRNA level of Nrf2 in HepG2 cells. Dibenzoylmethane induces HO-1 and Nrf2 protein expression, and the induction diminishes after 12 h[1]. Dibenzoylmethane (10, 20, 30, 40, 50 μM; 2 hours) concentration-dependently increases the phosphorylated protein levels of Erk1/2, p38MAPK, JNK, AMPK, and Akt in HepG2 cells.Dibenzoylmethane does not show significant cytotoxicity[1].

[In Vivo]

Dibenzoylmethane (200, 500 mg/kg/day; ip; for three consecutive days) pretreatment significantly reduces both the area and the severity of necrosis, as well as the leukocyte infiltration, at a dose of 200 mg/kg in wild-type and Nrf2 knockout mice[1]. Dibenzoylmethane protectes against CCl4-induced (1:49,v/v, 10 ml/kg) liver damage in wild-type mice[1].

[References]

[1]. Mingnan Cao, et al. Dibenzoylmethane Protects Against CCl4-Induced Acute Liver Injury by Activating Nrf2 via JNK, AMPK, and Calcium Signaling. AAPS J. 2017 Nov;19(6):1703-1714.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
357.4±0.0 °C at 760 mmHg

[ Melting Point ]:
77-79 °C(lit.)

[ Molecular Formula ]:
C₁₅H₁₂O₂

[ Molecular Weight ]:
224.255

[ Flash Point ]:
146.9±20.2 °C

[ Exact Mass ]:
224.083725

[ PSA ]:
34.14000

[ LogP ]:
3.04

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.584

[ Storage condition ]:
Store at RT.

[ Stability ]:
Stable. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TZ1930000

CHEMICAL NAME :: 1,3-Propanedione, 1,3-diphenyl-

CAS REGISTRY NUMBER :: 120-46-7

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C15-H12-O2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >500 mg/kg

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

REFERENCE :: NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. (Washington, DC) Volume(issue)/page/year: 5,28,1953 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4833 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 28 (estimated)

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
TZ1930000

[ HS Code ]:
2914399090

Synthetic Route

Click to get detail synthetic route

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

Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases.

J. Med. Chem. 48 , 2906-15, (2005)

Carboxylesterases (CE) are ubiquitous enzymes responsible for the metabolism of xenobiotics. Because the structural and amino acid homology among esterases of different classes, the identification of ...

A glimpse of the inner workings of the templated site.

Chem. Commun. (Camb.) (2) , 165-7, (2009)

This is the first direct experimental probe, using EXAFS, of the active site within molecularly imprinted polymers and paves the way to a more detailed understanding of the inner workings of molecular...

Combining ligand-based pharmacophore modeling, quantitative structure-activity relationship analysis and in silico screening for the discovery of new potent hormone sensitive lipase inhibitors.

J. Med. Chem. 51 , 6478-94, (2008)

Hormone sensitive lipase (HSL) has been recently implicated in diabetes and obesity, prompting attempts to discover new HSL inhibitors. Toward this end, we explored the pharmacophoric space of HSL inh...