Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H12O2 |
| Molecular Weight | 224.2546 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C(CC(=O)C1=CC=CC=C1)C2=CC=CC=C2
InChI
InChIKey=NZZIMKJIVMHWJC-UHFFFAOYSA-N
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
Dibenzoylmethane (DBM), a minor ingredient in licorice, is a calcium chelator that binds calcium through the β-diketone moiety, and it has been found to increase intracellular calcium concentrations in skeletal muscle cells. Intracellular calcium regulates the binding of Nrf2 to the HO-1 enhancer region. Both Nrf2 and HO-1 have been proposed as potential drug targets to prevent or treat liver disease. Thus was suggested DBM could be a lead/candidate for prevention or treatment of liver diseases. In addition, was found, that dibenzoylmethane inhibits mammary tumorigenesis, lymphomas, and leukemias in mice and it can prevent the formation of tumor-inducing DNA adducts.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Dimethoxycurcumin, a structural analogue of curcumin, induces apoptosis in human renal carcinoma caki cells through the production of reactive oxygen species, the release of cytochrome C, and the activation of caspase-3. | 2010-12 |
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| Cell death by the quinoxaline dioxide DCQ in human colon cancer cells is enhanced under hypoxia and is independent of p53 and p21. | 2010-11-15 |
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| Aggressive mammary carcinoma progression in Nrf2 knockout mice treated with 7,12-dimethylbenz[a]anthracene. | 2010-10-08 |
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| Ornithine decarboxylase prevents dibenzoylmethane-induced apoptosis through repressing reactive oxygen species generation. | 2010-09-15 |
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| A novel PVC-membrane optical sensor for highly sensitive and selective determination of UO2(2+) ion based on a recently synthesized benzo-substituted macrocyclic diamide and dibenzoylmethane. | 2010-09-15 |
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| Synthesis and characterization of calcium beta-diketonate complexes. X-ray crystal and molecular structures of: [{Ca(tmhd)2}2(18-crown-6)], [Ca(dpp)2(thf)2] and [Ca(dpp)2(triglyme)]. | 2010-09-14 |
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| CYP93G2 is a flavanone 2-hydroxylase required for C-glycosylflavone biosynthesis in rice. | 2010-09 |
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| New amino acid ligated yttrium hydroxy clusters. | 2010-08-07 |
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| Micelles as "fluorescence protector" for an europium complex in microcapsules. | 2010-07-20 |
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| Photophysical properties of a novel organic-inorganic hybrid material: Eu(III)-β-diketone complex covalently bonded to SiO(2) /ZnO composite matrix. | 2010-06-18 |
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| Bioavailability and delivery of nutraceuticals using nanotechnology. | 2010-05-25 |
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| Luminescence in colorless, transparent, thermally stable thin films of Eu3+ and Tb3+ beta-diketonates in hybrid inorganic-organic zinc-based sol-gel matrix. | 2010-05 |
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| Differential in vivo mechanism of chemoprevention of tumor formation in azoxymethane/dextran sodium sulfate mice by PEITC and DBM. | 2010-05 |
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| Anti-photoaging and photoprotective compounds derived from marine organisms. | 2010-04-08 |
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| Mouse models for unraveling the importance of diet in colon cancer prevention. | 2010-02 |
|
| UV absorption and keto-enol tautomerism equilibrium of methoxy and dimethoxy 1,3-diphenylpropane-1,3-diones. | 2010-02 |
|
| A new type of asymmetric tridentate pyrrolyl-linked pincer ligand and its aluminum dihydride complexes. | 2010-01-04 |
|
| Efficacy of dibenzoylmethane derivatives in protecting against endoplasmic reticulum stress and inhibiting nuclear factor kappa B on dextran sulfate sodium induced colitis in mice. | 2010 |
|
| Overexpression of the ATP binding cassette gene ABCA1 determines resistance to Curcumin in M14 melanoma cells. | 2009-12-23 |
|
| Optical and electron paramagnetic resonance studies of the excited states of 4-tert-butyl-4'-methoxydibenzoylmethane and 4-tert-butyl-4'-methoxydibenzoylpropane. | 2009-12-03 |
|
| Photodegradation of dibenzoylmethanes: potential cause of photocontact allergy to sunscreens. | 2009-11 |
|
| Dietary feeding of dibenzoylmethane inhibits prostate cancer in transgenic adenocarcinoma of the mouse prostate model. | 2009-09-01 |
|
| The radiosensitizer 2-benzoyl-3-phenyl-6,7-dichloroquinoxaline 1,4-dioxide induces DNA damage in EMT-6 mammary carcinoma cells. | 2009-07-14 |
|
| The C-glycosylation of flavonoids in cereals. | 2009-07-03 |
|
| Mechanisms of apoptotic effects induced by resveratrol, dibenzoylmethane, and their analogues on human lung carcinoma cells. | 2009-06-24 |
|
| Optical properties and spectroscope parameters of Sm(DBM)(3)Phen-doped poly(methyl methacrylate). | 2009-04 |
|
| Self-assembled SiO2 photonic crystal infiltrated by Ormosil:Eu(DBM)(3)phen phosphor and its enhanced photoluminescence. | 2009-03-02 |
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| A glimpse of the inner workings of the templated site. | 2009-01-08 |
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| Reversible modulation in luminescence intensity of a single vesicle composed of diblock azo-copolymer and tris(dibenzoylmethanate)(phenanthroline)europium(III). | 2009-01 |
|
| Carcinogenic effects in a phenylketonuria mouse model. | 2009 |
|
| Structural diversity in neodymium bipyrimidine compounds with near infrared luminescence: from mono- and binuclear complexes to metal-organic frameworks. | 2008-11-17 |
|
| Synthesis, spectroscopic characterization and biological activity of the metal complexes of the Schiff base derived from phenylaminoacetohydrazide and dibenzoylmethane. | 2008-11-01 |
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| High-throughput cell-based screening reveals a role for ZNF131 as a repressor of ERalpha signaling. | 2008-10-11 |
|
| A radical-anion chain mechanism following dissociative electron transfer reduction of the model prostaglandin endoperoxide, 1,4-diphenyl-2,3-dioxabicyclo[2.2.1]heptane. | 2008-09-21 |
|
| Dibenzoylmethane activates Nrf2-dependent detoxification pathway and inhibits benzo(a)pyrene induced DNA adducts in lungs. | 2008-09 |
|
| Cancer is a preventable disease that requires major lifestyle changes. | 2008-09 |
|
| Synthesis and spectroscopic examination of various substituted 1,3-dibenzoylmethane, active agents for UVA/UVB photoprotection. | 2008-08-21 |
|
| Simultaneous preconcentration and determination of U(VI), Th(IV), Zr(IV) and Hf(IV) ions in aqueous samples using micelle-mediated extraction coupled to inductively coupled plasma-optical emission spectrometry. | 2008-08-15 |
|
| Pentanuclear dysprosium hydroxy cluster showing single-molecule-magnet behavior. | 2008-08-04 |
|
| Synthesis and antimicrobial activity of some new pyrazole, fused pyrazolo[3,4-d]-pyrimidine and pyrazolo[4,3-e][1,2,4]-triazolo[1,5-c]pyrimidine derivatives. | 2008-07-29 |
|
| (Z)-3-Anilino-1,3-diphenylprop-2-en-1-one. | 2008-06-21 |
|
| Novel multicomponent reactions involving isoquinoline or phenanthridine and activated acetylenic ester in the presence of heterocyclic NH or 1,3-dicarbonyl compounds. | 2008-05 |
|
| Development of formaldehyde sensing element using porous glass impregnated with beta-diketone. | 2008-02-15 |
|
| Enantiomorphs of a carbene-ruthenium(II)-porphyrin complex with four 'chiral pillars'. | 2008-02 |
|
| Tetra- and dinuclear nickel(II)-vanadium(IV/V) heterometal complexes of a phenol-based N2O2 ligand: synthesis, structures, and magnetic and redox properties. | 2008-01-21 |
|
| Templated assembly of a mu6-CO3 2- dodecanuclear lanthanum dibenzoylmethanide hydroxido cluster with concomitant formation of phenylglyoxylate. | 2007-12-28 |
|
| Bis(2-benzoyl-1-phenyl-ethenolato-κO,O')(ethanol-κO)dioxidouranium(VI). | 2007-12-18 |
|
| Chemoprevention of familial adenomatous polyposis by natural dietary compounds sulforaphane and dibenzoylmethane alone and in combination in ApcMin/+ mouse. | 2007-10-15 |
|
| Intramolecular hydrogen bonding (proton transfer) of 1-phenyl-1,3-butanedione. | 2007 |
|
| Solvent extraction of metals with potassium-dihydro-bispyrazolyl-borate. | 2002-06-10 |
Patents
Sample Use Guides
Feeding 1% dibenzoylmethane (DBM) diet to Sencar mice inhibited formation of 7,12-dimethylbenz[a]anthracene (DMBA)-DNA adducts in mammary glands and lowered the proliferation rate of the mammary gland in vivo
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: Dibenzoylmethane (DBM) increases HIF-1 alpha protein levels in a dose- and time-dependent manner. This induction was accompanied with activation of HIF-1, measured by reporter gene assay and increased production of its downstream target, the vascular endothelial growth factor. Mechanistically, HIF-1 alpha was stabilized by DBM at a step prior to ubiquitination.
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SUBSTANCE RECORD
