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Chalcone information


Chalcone[1]
Skeletal formula of chalcone
Ball-and-stick model of the chalcone molecule
Names
Preferred IUPAC name
Chalcone[2]
Systematic IUPAC name
(2E)-1,3-Diphenylprop-2-en-1-one
Other names
Chalkone
Benzylideneacetophenone
Phenyl styryl ketone
benzalacetophenone
β-phenylacrylophenone
γ-oxo-α,γ-diphenyl-α-propylene
α-phenyl-β-benzoylethylene.
Identifiers
CAS Number
  • 94-41-7
  • 614-47-1 ((E)-Chalcone) checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:27618 checkY
ChemSpider
  • 6921 checkY
ECHA InfoCard 100.002.119 Edit this at Wikidata
PubChem CID
  • 637760
UNII
  • 5S5A2Q39HX checkY
CompTox Dashboard (EPA)
  • DTXSID20873536 Edit this at Wikidata
InChI
  • InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H checkY
    Key: DQFBYFPFKXHELB-UHFFFAOYSA-N checkY
  • InChI=1/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H
    Key: DQFBYFPFKXHELB-UHFFFAOYAP
SMILES
  • O=C(C=Cc1ccccc1)c2ccccc2
Properties
Chemical formula
C15H12O
Molar mass 208.260 g·mol−1
Appearance pale yellow solid
Density 1.071 g/cm3
Melting point 55 to 57 °C (131 to 135 °F; 328 to 330 K)
Boiling point 345 to 348 °C (653 to 658 °F; 618 to 621 K)
Magnetic susceptibility (χ)
-125.7·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids.[3] They are widely known bioactive substances, fluorescent materials, and chemical intermediates.

  1. ^ Merck Index, 11th Edition, 2028
  2. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 722. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  3. ^ Tomás-Barberán, Francisco A.; Clifford, Michael N. (2000). "Flavanones, Chalcones and Dihydrochalcones - Nature, Occurrence and Dietary Burden". Journal of the Science of Food and Agriculture. 80 (7): 1073–1080. doi:10.1002/(SICI)1097-0010(20000515)80:7<1073::AID-JSFA568>3.0.CO;2-B.

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Chalcone

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Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively...

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Chalcone synthase

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Chalcone synthase or naringenin-chalcone synthase (CHS) is an enzyme ubiquitous to higher plants and belongs to a family of polyketide synthase enzymes...

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Flavones

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carboxylate facilitated by 4-Coumarate-CoA ligase, forming (Coumaroyl-CoA). A chalcone synthase then facilitates a series of condensation reactions in the presence...

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Naringenin chalcone

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Naringenin chalcone is a common chalconoid (or chalcone, not to be confused with the compound chalcone). It is synthesized from 4-coumaroyl-CoA and malonyl-CoA...

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Apigenin

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malonyl CoA followed by aromatization to convert p-coumaroyl-CoA to chalcone. Chalcone isomerase (CHI) then isomerizes the product to close the pyrone ring...

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Chalconoid

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khalkós, "copper", due to its color), also known as chalcones, are natural phenols derived from chalcone. They form the central core for a variety of important...

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Hesperidin

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naringenin chalcone synthase, undergoing successive condensation reactions and ultimately a ring-closing Claisen condensation to afford naringenin chalcone. The...

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Anthocyanin

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streams meet and are coupled together by the enzyme chalcone synthase, which forms an intermediate chalcone-like compound via a polyketide folding mechanism...

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Kaempferol

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malonyl-CoA to form naringenin chalcone (tetrahydroxychalcone) through the action of the enzyme chalcone synthase Naringenin chalcone is converted to naringenin...

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Chalcone isomerase

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In enzymology, a chalcone isomerase (EC 5.5.1.6) is an enzyme that catalyzes the chemical reaction a chalcone ⇌ {\displaystyle \rightleftharpoons } a flavanone...

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Rutin

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Subsequently, chalcone synthase (CHS) catalyzes the condensation of p-coumaroyl-CoA and three molecules of malonyl-CoA to produce naringenin chalcone, which...

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Bioisostere

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in a series of anti-bacterial chalcones. By modifying certain substituents, the pharmacological activity of the chalcone and its toxicity are also modified...

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Cinnamomum mercadoi

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Cinnamomum mercadoi (kalingag) is a small tree, about 6 to 10 metres (20 to 33 ft) high, with a thick, aromatic bark. The plant part of the family Lauraceae...

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Flavanone

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Poncirin Sakuranetin Sakuranin Sterubin Pinostrobin The enzyme chalcone isomerase uses a chalcone-like compound to produce a flavanone. Flavanone 4-reductase...

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Ketoacyl synthase

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reactions before the final chalcone product is formed. Chalcone synthase (E.C. 2.3.1.74), also known as naringenin-chalcone synthase, is responsible for...

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Catechin

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4-hydroxylase. Chalcone synthase then catalyzes the condensation of 4-hydroxycinnamoyl CoA and three molecules of malonyl-CoA to form chalcone. Chalcone is then...

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Flavonoid biosynthesis

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flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids...

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Fisetin

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pathway. Chalcone synthase, the first enzyme of this pathway, produces chalcone from 4-coumaroyl-CoA. All flavonoids are derived from this chalcone backbone...

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RNA

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Napoli C, Lemieux C, Jorgensen R (April 1990). "Introduction of a Chimeric Chalcone Synthase Gene into Petunia Results in Reversible Co-Suppression of Homologous...

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Cyanidin

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CoA to the carboxylic acid group. The compound reacts with naringenin-chalcone synthase and three malonyl CoA molecules to add six carbon atoms and three...

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Isoflavone

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naringenin chalcone is converted to the isoflavone daidzein by sequential action of three legume-specific enzymes: chalcone reductase, type II chalcone isomerase...

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Silibinin

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carbon chain elongation with malonyl-CoA and cyclization by chalcone synthase and chalcone isomerase to yield naringenin. Through flavanone 3-hydroxylase...

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Daidzein

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which enzymes chalcone synthase (CHS) and chalcone reductase (CHR) modify to obtain trihydroxychalcone. CHR is NADPH dependent. Chalcone isomerase (CHI)...

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Quercetin

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synthase. Tetrahydroxychalcone is then converted into naringenin using chalcone isomerase. Naringenin is converted into eriodictyol using flavanoid 3′-hydroxylase...

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Alkyl group

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has been used to increase the antimicrobial activity of flavanones and chalcones. Usually, alkyl groups are attached to other atoms or groups of atoms...

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