Methyl caffeate

Methyl caffeate
	; Chemical structure of methyl caffeate
Names
	Preferred IUPAC name Methyl (2E)-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	194.186 g·mol−1
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 caffeic acid, a naturally occurring phenolic compound. It is an α-glucosidase inhibitor.^[1] Its physical form is a powder.

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]

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. hdl:2115/53430. PMID 20378981. S2CID 23067847.
^ ^a ^b Gandhi, Gopalsamy Rajiv; Ignacimuthu, Savarimuthu; Paulraj, Michael Gabriel; Sasikumar, Ponnusamy (2011). "Antihyperglycemic activity and antidiabetic effect of methyl caffeate isolated from Solanum torvum Swartz. Fruit in streptozotocin induced diabetic rats". European Journal of Pharmacology. 670 (2–3): 623–631. doi:10.1016/j.ejphar.2011.09.159. PMID 21963451.

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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. hdl:2115/53430. PMID 20378981. S2CID 23067847.

[Gandhi-2] Gandhi, Gopalsamy Rajiv; Ignacimuthu, Savarimuthu; Paulraj, Michael Gabriel; Sasikumar, Ponnusamy (2011). "Antihyperglycemic activity and antidiabetic effect of methyl caffeate isolated from Solanum torvum Swartz. Fruit in streptozotocin induced diabetic rats". European Journal of Pharmacology. 670 (2–3): 623–631. doi:10.1016/j.ejphar.2011.09.159. PMID 21963451.

[1]

[2]

Names
Chemical structure of methyl caffeate
Preferred IUPAC name Methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Other names Caffeic acid methyl ester methylcaffeate Methyl 3,4-dihydroxycinnamate
Identifiers
CAS Number	3843-74-1^Y
3D model (JSmol)	Interactive image
ChemSpider	600455
ECHA InfoCard	100.236.052
PubChem CID	689075
UNII	N79173B9HF^Y
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	194.186 g·mol⁻¹
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

Natural occurrences

Health effect

References

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