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Names | |
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Preferred IUPAC name 1,3-Diphenylpropane-1,3-dione | |
Other names 2-Benzoylacetophenone | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.003.999 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C15H12O2 | |
Molar mass | 224.25 g/mol |
Appearance | white solid |
Density | 1.334 g/cm3 |
Melting point | 77 to 78 °C (171 to 172 °F; 350 to 351 K) [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Dibenzoylmethane (DBM) is an organic compound with the formula (C6H5C(O))2CH2. DBM is the name for a 1,3-diketone, but the compound exists primarily as one of two equivalent enol tautomers. [2] DBM (actually its enol) is a white solid. Due to their high photostability and UV-absorbing properties, derivatives of DBM such as avobenzone, have found applications as sunscreen products.
DBM is prepared by condensation of ethyl benzoate with acetophenone. [3]
Like other 1,3-diketones (or their enols), DBM condenses with a variety of bifunctional reagents to give heterocycles. Hydrazine gives diphenylpyrazole. Urea and thiourea also condense to give six-membered rings. With metal salts, the conjugate base of DBM forms complexes akin to the metal acetylacetonates.
Dibenzoylmethane (DBM) is a minor constituent in the root extract of Licorice (Glycyrrhiza glabra in the family Leguminosae). [4] It is also found in Curcumin. These occurrences have led to investigations into the medicinal properties of this class of compounds. [5] [6]
DBM (and Trazodone) slow disease progression by preventing the cessation of protein synthesis in neurons. [7]
In organic chemistry, a ketone is a functional group with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.
Purine is a heterocyclic aromatic organic compound that consists of two rings fused together. It is water-soluble. Purine also gives its name to the wider class of molecules, purines, which include substituted purines and their tautomers. They are the most widely occurring nitrogen-containing heterocycles in nature.
In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are common and are important in technology and biology.
Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is the first chemical step in photosynthesis, is called carboxylation, the addition of CO2 to a compound. Enzymes that catalyze decarboxylations are called decarboxylases or, the more formal term, carboxy-lyases (EC number 4.1.1).
Curcumin is a bright yellow chemical produced by plants of the Curcuma longa species. It is the principal curcuminoid of turmeric, a member of the ginger family, Zingiberaceae. It is sold as a herbal supplement, cosmetics ingredient, food flavoring, and food coloring.
Hydrazones are a class of organic compounds with the structure R1R2C=N−NH2. They are related to ketones and aldehydes by the replacement of the oxygen =O with the =N−NH2 functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.
In organic chemistry, a dicarbonyl is a molecule containing two carbonyl groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical or unsymmetrical.
An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates.
In organic chemistry, alkenols are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene (olefin) with a hydroxyl group attached to one end of the alkene double bond. The terms enol and alkenol are portmanteaus deriving from "-ene"/"alkene" and the "-ol" suffix indicating the hydroxyl group of alcohols, dropping the terminal "-e" of the first term. Generation of enols often involves removal of a hydrogen adjacent (α-) to the carbonyl group—i.e., deprotonation, its removal as a proton, H+. When this proton is not returned at the end of the stepwise process, the result is an anion termed an enolate. The enolate structures shown are schematic; a more modern representation considers the molecular orbitals that are formed and occupied by electrons in the enolate. Similarly, generation of the enol often is accompanied by "trapping" or masking of the hydroxy group as an ether, such as a silyl enol ether.
Tautomers are structural isomers of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism. Tautomerism is for example relevant to the behavior of amino acids and nucleic acids, two of the fundamental building blocks of life.
Acetylacetone is an organic compound with the chemical formula CH3COCH2COCH3. It is a colorless liquid, classified as a 1,3-diketone. It exists in equilibrium with a tautomer CH3C(O)CH=(OH)CH3. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications. It is a colorless liquid that is a precursor to acetylacetonate anion, a bidentate ligand. It is also a building block for the synthesis of heterocyclic compounds.
Aromatization is a chemical reaction in which an aromatic system is formed from a single nonaromatic precursor. Typically aromatization is achieved by dehydrogenation of existing cyclic compounds, illustrated by the conversion of cyclohexane into benzene. Aromatization includes the formation of heterocyclic systems.
Avobenzone is an oil-soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays.
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is a colorless liquid. It is widely used as a chemical intermediate in the production of a wide variety of compounds. It is used as a flavoring for food.
UV filters are compounds, mixtures, or materials that block or absorb ultraviolet (UV) light. One of the major applications of UV filters is their use as sunscreens to protect skin from sunburn and other sun/UV related damage. After the invention of digital cameras changed the field of photography, UV filters have been used to coat glass discs fitted to camera lenses to protect hardware that is sensitive to UV light.
Diallyl disulfide is an organosulfur compound derived from garlic and a few other genus Allium plants. Along with diallyl trisulfide and diallyl tetrasulfide, it is one of the principal components of the distilled oil of garlic. It is a yellowish liquid which is insoluble in water and has a strong garlic odor. It is produced during the decomposition of allicin, which is released upon crushing garlic and other plants of the family Alliaceae. Diallyl disulfide has many of the health benefits of garlic, but it is also an allergen causing garlic allergy. Highly diluted, it is used as a flavoring in food. It decomposes in the human body into other compounds such as allyl methyl sulfide.
A postzygotic mutation is a change in an organism's genome that is acquired during its lifespan, instead of being inherited from its parent(s) through fusion of two haploid gametes. Mutations that occur after the zygote has formed can be caused by a variety of sources that fall under two classes: spontaneous mutations and induced mutations. How detrimental a mutation is to an organism is dependent on what the mutation is, where it occurred in the genome and when it occurred.
Dimedone is an organic compound with the formula (CH3)2C(CH2)2(CO)2(CH2). Classified as a cyclic diketone, it is a derivative of 1,3-cyclohexanedione. It is a white solid that is soluble in water, as well as ethanol and methanol. It once was used as a reagent to test for the aldehyde functional group.
2-Hydroxy-3-methyl-2-cyclopenten-1-one is an organic compound related to 1,2-cyclopentanedione. It is the enol tautomer of the diketone 3-methylcyclopentane-1,2-dione. Being an enol, the compound is often called methylcyclopentenolone. It is a colorless solid.
In organic chemistry, the Conia-ene reaction is an intramolecular cyclization reaction between an enolizable carbonyl such as an ester or ketone and an alkyne or alkene, giving a cyclic product with a new carbon-carbon bond. As initially reported by J. M. Conia and P. Le Perchec, the Conia-ene reaction is a heteroatom analog of the ene reaction that uses an enol as the ene component. Like other pericyclic reactions, the original Conia-ene reaction required high temperatures to proceed, limiting its wider application. However, subsequent improvements, particularly in metal catalysis, have led to significant expansion of reaction scope. Consequently, various forms of the Conia-ene reaction have been employed in the synthesis of complex molecules and natural products.