Methyl hydroxychalcone

Methyl hydroxychalcone
Chemical structure of methyl hydroxychalcone
Names
Preferred IUPAC name
3-Hydroxy-3′-methylchalcone
Other names
MCHP
3'-Methyl-3-hydroxychalcone
Identifiers
CAS Number
  • 153976-41-1 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4944650 ☒N
PubChem CID
  • 6440383
CompTox Dashboard (EPA)
  • DTXSID801028833 Edit this at Wikidata
InChI
  • InChI=1S/C16H14O2/c1-12-4-2-6-14(10-12)16(18)9-8-13-5-3-7-15(17)11-13/h2-11,17H,1H3/b9-8+ ☒N
    Key: GPJXEEMHEDUKIP-CMDGGOBGSA-N ☒N
  • InChI=1/C16H14O2/c1-12-4-2-6-14(10-12)16(18)9-8-13-5-3-7-15(17)11-13/h2-11,17H,1H3/b9-8+
    Key: GPJXEEMHEDUKIP-CMDGGOBGBY
  • CC1=CC=CC(=C1)C(=O)C=CC2=CC(=CC=C2)O
Properties
Chemical formula
 C16H14O2
Molar mass 238.28 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

Methyl hydroxychalcone is a chalconoid found in cinnamon. It was thought to be an insulin mimetic, improving insulin response of diabetics.[1] It has since been determined that a flavonoid (cinnamtannin B1) is responsible for the insulin-like biological activity.[2]

See also

  • Anti-diabetic medication

References

  1. ^ Karalee J. Jarvill-Taylor, PhD; Richard A. Anderson, PhD; Donald J. Graves, PhD (August 1, 2001). "A hydroxychalcone derived from cinnamon functions as a mimetic for insulin in 3T3-L1 adipocytes". J Am Coll Nutr. 20 (4): 327–36. doi:10.1080/07315724.2001.10719053. PMID 11506060. S2CID 34049517. Archived from the original on 2004-08-11. Retrieved 2014-02-27.
  2. ^ Anderson; Broadhurst, CL; Polansky, MM; Schmidt, WF; Khan, A; Flanagan, VP; Schoene, NW; Graves, DJ (January 2004). "Isolation and characterization of polyphenol type-A polymers from cinnamon with insulin-like biological activity". J Agric Food Chem. 52 (1): 65–70. doi:10.1021/jf034916b. PMID 14709014.


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Chalconoids and their glycosides
Chalconoids
  • Butein
  • Isoliquiritigenin
  • Methyl hydroxychalcone
  • Okanin
Chalconoid glycosides
  • Carthamin
  • Marein
  • okanin 3,4,3′-trimethyl ether 4′-glucoside
  • okanin 4-methyl ether 4′-glucoside
  • okanin 4-methyl ether 4′-glucoside monoacetate
  • Okanin 3,4-dimethyl ether 4′-glucoside
Acylated chalconoids
O-methylated chalconoids
  • Cardamomin
  • Flavokawin B
  • Okanin 3,4,3′,4′-tetramethyl ether
  • Pashanone (2',6'-Dihydroxy-3',4'-dimethoxychalcone)
FlavokavainsSynthetic


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