Dihydrochalcone

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Dihydrochalcone
Dihydrochalcone alternate.svg
Names
Preferred IUPAC name
1,3-Diphenylpropan-1-one
Other names
Hydrochalcone
Benzylacetophenone
Hydrocinnamophenone
3-Phenylpropiophenone
Phenethyl phenyl ketone
Phenyl phenethyl ketone
β-Phenylpropiophenone
1,3-Diphenyl-1-propanone
ω-Benzyl acetophenone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.150.317 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C15H14O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-10H,11-12H2 Yes check.svgY
    Key: QGGZBXOADPVUPN-UHFFFAOYSA-N Yes check.svgY
  • C1=CC=C(C=C1)CCC(=O)C2=CC=CC=C2
Properties
C15H14O
Molar mass 210.27 g/mol
Appearancewhite solid
Density 1.0614 g/cm3
Melting point 72–75 °C (162–167 °F; 345–348 K)
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

Dihydrochalcone (DHC) is the organic compound with the formula C6H5C(O)(CH2)2C6H5. It is the reduced derivative of chalcone (C6H5C(O)(CH)2C6H5). It is white solid that is soluble in many organic solvents. Dihydrochalcone per se is often minor significance, but some derivatives occur in nature and have attracted attention as drugs. [1]

Natural dihydrochalcones

Neohesperidin dihydrochalcone is a commercial artificial sweetener that features the dihydrochalcone substituent. Neohesperidin dihydrochalcone.png
Neohesperidin dihydrochalcone is a commercial artificial sweetener that features the dihydrochalcone substituent.

Dihydrochalcones (3′,5′-dihydroxy-2′,4′,6′-trimethoxydihydrochalcone (methyl linderone) and 2′-hydroxy-3′,4′,5′,6′-tetramethoxydihydrochalcone (dihydrokanakugiol) can be found in twigs of Lindera lucida . [2]

Related Research Articles

Oxime

An oxime is a chemical compound belonging to the imines, with the general formula RR'C=NOH, where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides with general structure R1C(=NOH)NR2R3.

Neohesperidin dihydrochalcone Chemical compound

Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus.

The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds, resulting in "a fully conjugated cyclic dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone". Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.

A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes.

Chalcone Chemical compound

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.

Phloroglucinol Chemical compound

Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed "polyphenols" by the cosmetic and parapharmaceutical industries, which does not match the scientifically accepted definition.

Pyrazole is an organic compound with the formula C3H3N2H. It is a heterocycle characterized by a 5-membered ring of three carbon atoms and two adjacent nitrogen atoms. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C). Pyrazoles are also a class of compounds that have the ring C3N2 with adjacent nitrogen atoms. Notable drugs containing a pyrazole ring are celecoxib (Celebrex) and the anabolic steroid stanozolol.

Hesperidin Chemical compound

Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone form is called hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.

Apigenin Chemical compound

Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.

Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.

Aspalathin Chemical compound

Aspalathin is a C-linked dihydrochalcone glucoside found in rooibos tea, a herbal tea prepared from the South African rooibos plant, Aspalathus linearis (Fabaceae).

Nothofagin Chemical compound

Nothofagin is a dihydrochalcone. It is a C-linked phloretin glucoside found in rooibos and New Zealand red beech. It is a phenolic antioxidant.

Naringin dihydrochalcone Chemical compound

Naringin dihydrochalcone, sometimes abbreviated to naringin DC, is an artificial sweetener derived from naringin, a bitter compound found in citrus.

Phlorizin Chemical compound

Phlorizin is a glucoside of phloretin, a dihydrochalcone. A white solid, samples often appear yellow owing to impurities. It is of sweet taste and contains four molecules of water in the crystal. Above 200 °C, it decomposes to give rufin. It is poorly soluble in ether and cold water, but soluble in ethanol and hot water. Upon prolonged exposure to aqueous solutions phlorizin hydrolyzes to phloretin and glucose.

Phloretin Chemical compound

Phloretin is a dihydrochalcone, a type of natural phenol. It can be found in apple tree leaves and the Manchurian apricot.

Aurone Chemical compound

An aurone is a heterocyclic chemical compound which is a type of flavonoid. There are two isomers of the molecule, with (E)- and (Z)-configurations. The molecule contains a benzofuran element associated with a benzylidene linked in position 2. In aurone, a chalcone-like group is closed into a 5-membered ring instead of the 6-membered ring more typical of flavonoids.

Lindera lucida is a species of flowering plant in the family Lauraceae. It is found in Malaysia.

Aureusidin synthase is an enzyme with systematic name 2',4,4',6'-tetrahydroxychalcone 4'-O-beta-D-glucoside:oxygen oxidoreductase.

Dihydrokanakugiol Chemical compound

Dihydrokanakugiol is a dihydrochalcone isolated from Lindera lucida.

Linderone Chemical compound

Linderone is a bio-active isolate of Lindera lucida.

References

  1. 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.
  2. A dihydrochalcone from Lindera lucida. Yuan-Wah Leong, Leslie J. Harrison, , Graham J. Bennett, Azizol A. Kadir and Joseph D. Connolly, Phytochemistry, Volume 47, Issue 5, March 1998, Pp. 891-894, doi : 10.1016/S0031-9422(97)00947-3