Methyl hydroxychalcone

Methyl hydroxychalcone
Names
	Preferred IUPAC name 3-Hydroxy-3′-methylchalcone
	Other names MCHP; 3'-Methyl-3-hydroxychalcone
Identifiers
CAS Number	153976-41-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	4944650 ;
PubChem CID	6440383;
CompTox Dashboard (EPA)	DTXSID801028833 ;
	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+ Key: GPJXEEMHEDUKIP-CMDGGOBGSA-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;
	SMILES 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). verify (what is ?) Infobox references

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]

References

^ 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.
^ 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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[MCHP_insulin-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.

[polyphenol_insulin-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.

[1]

[2]

v t e 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	Licochalcone A Sophoradin (prenylated) Tephrospinosin (3′,5′-diisopentenyl-2′,4′-dihydroxychalcone) (prenylated) Xanthohumol (prenylated)
O-methylated chalconoids	Cardamomin Flavokawin B Okanin 3,4,3′,4′-tetramethyl ether Pashanone (2',6'-Dihydroxy-3',4'-dimethoxychalcone)
Flavokavains	Flavokavain A Flavokavain B Flavokavain C
Synthetic	Sofalcone

See also

References