| Identification | More | [Name]
Dibenzoylmethane | [CAS]
120-46-7 | [Synonyms]
1,3-DIPHENYL-1,3-PROPANEDIONE
1,3-diphenylpropane-1,3-dione
DBM
DIBENZOYLMETHANE
,3-Diphenyl-propane-1,3-dione
1,3-Diphenyl-1,3-propanediamine
1,3-diphenyl-3-propanedione
1,3-Diphenylpropanedione
2-Benzoylacetophenone
3-Propanedione,1,3-diphenyl-1
arenzu dk 2
-Benzoylacetophenone
-Benzoylace-tophenone
Dibenzoylmethan
hodiastab 83
-Hydroxy-chalkone
karenzudk2
omega-Benzoylacetophenone
Phenyl phenacyl ketone
Phenyl-hydroxystyrylketone | [EINECS(EC#)]
204-398-9 | [Molecular Formula]
C15H12O2 | [MDL Number]
MFCD00003085 | [Molecular Weight]
224.25 | [MOL File]
120-46-7.mol |
| Chemical Properties | Back Directory | [Appearance]
yellowish-white powder | [Melting point ]
77-79 °C(lit.)
| [Boiling point ]
219-221 °C18 mm Hg(lit.)
| [density ]
0.800 g/cm3 | [vapor pressure ]
0.01Pa at 20℃ | [refractive index ]
1.6600 (estimate) | [Fp ]
219-221°C/18mm | [storage temp. ]
Store at RT. | [solubility ]
Chloroform (Slightly), Methanol (Slightly, Sonicated) | [form ]
Crystals | [pka]
8.95±0.10(Predicted) | [color ]
Light yellow to yellow | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Water Solubility ]
It is Soluble in ether, chloroform, and aqueous sodium hydroxide. Insoluble in water. | [Merck ]
14,3009 | [BRN ]
514910 | [Henry's Law Constant]
7.5×103 mol/(m3Pa) at 25℃, Zhang et al. (2010) | [InChI]
1S/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-10H,11H2 | [InChIKey]
NZZIMKJIVMHWJC-UHFFFAOYSA-N | [SMILES]
O=C(CC(=O)c1ccccc1)c2ccccc2 | [LogP]
4.59 at 25℃ | [CAS DataBase Reference]
120-46-7(CAS DataBase Reference) | [NIST Chemistry Reference]
1,3-Propanedione, 1,3-diphenyl-(120-46-7) | [EPA Substance Registry System]
120-46-7(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P271-P280 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
TZ1930000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29143900 | [Storage Class]
11 - Combustible Solids | [Safety Profile]
Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors | [Toxicity]
rat,LD,oral,> 500mg/kg (500mg/kg),National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 28, 1953. |
| Raw materials And Preparation Products | Back Directory | [Preparation Products]
3,5-DIPHENYLPYRAZOLE-->1,2,4,5-tetraphenylbenzene-->1,2-Bis(p-tolylsulfonyl)hydrazine, N,Nμ-Ditosylhydrazine, 4-Methylbenzenesulfonic acid 2-[(4-methylphenyl)sulfonyl]hydrazide-->3-Benzoyl-2-phenylnaphtho[2,3-b]furan-4,9-dione-->1-Butanone, 4-(4-nitrophenyl)-1-phenyl- |
| Hazard Information | Back Directory | [Chemical Properties]
yellowish-white powder | [Occurrence]
Dibenzoylmethane(DBM) is a 1,3-diketone derivative of acetylacetone that has both methyl groups replaced with phenyl groups.Although smaller in size and lacking hydroxyl and methoxy groups，DBM resembles the turmeric spice curcumin (CUR),a diferuloylmethane. Both molecules are metal-chelating agents，contain a B-diketone flanked by two aryl groups,and exhibit anti-proliferative and anticarcinogenic activity. In addition to sharing structural similarity with DBM,CUR,which is also a naturally occurring compound is found in the plant Curcuma longa and has numerous medicinal uses.
DBM and its many naturally occurring derivatives are minor constituentsof licorice. DBM has been isolated from licorice root extracts and otherspecies of Glycyrrhiza. | [Uses]
antineoplastic | [Uses]
dibenzoylmethane as a new PVC heat stabilizer, high transmittance, non-toxic and tasteless; can greatly improve the early PVC coloring, transparency, long-term stability, and processing during precipitation and "zinc burn" and so on; widely used in medical, food packaging and other non-toxic transparent PVC products. Dibenzoylmethane above can absorb 290nm ultraviolet light, while light having a stabilizing effect on PVC products can provide long-term stable performance. | [Definition]
ChEBI: A beta-diketone that is acetylacetone (acac) in which both methyl groups have been replaced by phenyl groups. It is a minor constituent of the root extract of licorice (Glycyrrhiza glabra) and exhibits antimutagenic and antica
cer effects. | [Preparation]
dibenzoylmethane is prepared by condensation of ethyl benzoate with acetophenone. | [Synthesis Reference(s)]
Tetrahedron Letters, 37, p. 3885, 1996 DOI: 10.1016/0040-4039(96)00689-2
Chemical and Pharmaceutical Bulletin, 29, p. 2762, 1981 DOI: 10.1248/cpb.29.2762 | [Flammability and Explosibility]
Nonflammable | [Biological Activity]
In a screen of 300 compounds for those that regulate ER stress, the DBM (Dibenzoylmethane) derivative 14-26 (2,2'-dimethoxydibenzoylmethane) was identified as a novel neuroprotective agent. Other DBM derivatives that have been successfully used in protection against ER stress are 4,4'-dibromodibenzoylmethane and 4,4'-dichlorodibenzoyl-methane. Both compounds showed their protective effect against ER stress in F9 homocysteine-induced ER protein (Herp)-null cells treated with Tm[1]. | [Purification Methods]
Dibenzoylmethane (1,3-diphenyl-1,3-propanedione) [120-46-7] M 224.3, m 8 0o. Crystallise dibenzoylmethane from pet ether or MeOH. [Beilstein 7 IV 2512.] | [References]
[1] HONORATA KRASKIEWICZ Una F. InterfERing with endoplasmic reticulum stress.[J]. Trends in pharmacological sciences, 2012, 33 2: 53-63. DOI:10.1016/j.tips.2011.10.002.
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