Methyl caffeate

Methyl caffeate
	; Chemical structure of methyl caffeate
Names
	IUPAC name methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
	Other names Caffeic acid methyl ester; methylcaffeate; Methyl 3,4-dihydroxycinnamate
Identifiers
CAS Number	3843-74-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	600455;
ECHA InfoCard	100.236.052
PubChem CID	689075;
UNII	N79173B9HF ;
	InChI InChI=1S/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3/b5-3+ Key: OCNYGKNIVPVPPX-HWKANZROSA-N; InChI=1/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3/b5-3+ Key: OCNYGKNIVPVPPX-HWKANZROBE;
	SMILES COC(=O)/C=C/C1=CC(=C(C=C1)O)O;
Properties
Chemical formula	C10H10O4
Molar mass	194.18 g/mol
Related compounds
Related compounds	Caffeic acid, Ethyl caffeate
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Methyl caffeate is an ester of a hydroxycinnamic acid, a naturally occurring phenolic compound. It is an α-Glucosidase inhibitor.[1]

Natural occurrences

Methyl caffeate can be found in the fruit of Solanum torvum.[2]

Health effect

Methyl caffeate shows an antidiabetic effect in streptozotocin-induced diabetic rats.[2]

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References

Takahashi, Keisuke; Yoshioka, Yasuyuki; Kato, Eisuke; Katsuki, Shigeki; Iida, Osamu; Hosokawa, Keizo; Kawabata, Jun (2014). "Methyl Caffeate as an α-Glucosidase Inhibitor from Solanum torvum Fruits and the Activity of Related Compounds". Bioscience, Biotechnology, and Biochemistry. 74 (4): 741–745. doi:10.1271/bbb.90789. PMID 20378981.
Antihyperglycemic activity and antidiabetic effect of methylcaffeate isolated from Solanum torvum Swartz. fruit in streptozotocin induced diabetic rats. Gopalsamy Rajiv Gandhi, Savarimuthu Ignacimuthu, Michael Gabriel Paulraj, Ponnusamy Sasikumar, European Journal of Pharmacology, Volume 670, Issues 2–3, 30 November 2011, Pages 623–631, doi:10.1016/j.ejphar.2011.09.159

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[1] Takahashi, Keisuke; Yoshioka, Yasuyuki; Kato, Eisuke; Katsuki, Shigeki; Iida, Osamu; Hosokawa, Keizo; Kawabata, Jun (2014). "Methyl Caffeate as an α-Glucosidase Inhibitor from Solanum torvum Fruits and the Activity of Related Compounds". Bioscience, Biotechnology, and Biochemistry. 74 (4): 741–745. doi:10.1271/bbb.90789. PMID 20378981.

[Gandhi-2] Antihyperglycemic activity and antidiabetic effect of methylcaffeate isolated from Solanum torvum Swartz. fruit in streptozotocin induced diabetic rats. Gopalsamy Rajiv Gandhi, Savarimuthu Ignacimuthu, Michael Gabriel Paulraj, Ponnusamy Sasikumar, European Journal of Pharmacology, Volume 670, Issues 2–3, 30 November 2011, Pages 623–631, doi:10.1016/j.ejphar.2011.09.159