Methyl caffeate - Misplaced Pages

Methyl caffeate
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
3D model (JSmol)	Interactive image
ChemSpider	600455
ECHA InfoCard	100.236.052
PubChem CID	689075
UNII	N79173B9HF
CompTox Dashboard (EPA)	DTXSID401030290
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
Related compounds
Related compounds	Caffeic acid, Ethyl caffeate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Methyl caffeate is an ester of caffeic acid, a naturally occurring phenolic compound. It is an α-glucosidase inhibitor. Its physical form is a powder.

Natural occurrences

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

Health effect

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

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.
^ 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.

Types of hydroxycinnamic acids

Aglycones

Precursor	Cinnamic acid
Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid
Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid
Trihydroxycinnamic acids	2,4,5-Trihydroxycinnamic acid 3,4,5-Trihydroxycinnamic acid
O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Isoferulic acid Sinapinic acid
others	Plicatin A Plicatin B

Esters

glycoside-likes

Esters of
caffeic acid
with cyclitols

esters of quinic acid	Chlorogenic acid (3-caffeoylquinic acid) Cryptochlorogenic acid (4-O-caffeoylquinic acid) Neochlorogenic acid (5-O-Caffeoylquinic acid) Cynarine (1,5-dicaffeoylquinic acid) 3,4-dicaffeoylquinic acid 3,5-dicaffeoylquinic acid
esters of shikimic acid	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Tartaric acid esters

Caftaric acid
Chicoric acid (dicaffeoyltartaric acid)
Coutaric acid
Fertaric acid
Grape reaction product (caftaric acid conjugated with glutathione)

Other esters
with caffeic acid

Caffeoylmalic acid
Ethyl caffeate
Methyl caffeate
Caffeic acid phenethyl ester (CAPE)
Rosmarinic acid (ester with 3,4-dihydroxyphenyllactic acid)

Caffeoyl phenylethanoid
glycoside (CPG)

Echinacoside
Calceolarioside A, B, C, F
Chiritoside A, B, C
Cistanoside A, B, C, D, E, F, G, H
Conandroside
Myconoside
Pauoifloside
Plantainoside A
Plantamajoside
Tubuloside B
Verbascoside (Isoverbascoside, 2′-Acetylverbascoside)

Oligomeric forms

Dimers	Diferulic acids (DiFA) : 5,5′-Diferulic acid, 8-O-4′-Diferulic acid, 8,5′-Diferulic acid, 8,5′-DiFA (DC), 8,5′-DiFA (BF), 8,8′-Diferulic acid
Trimers	Triferulic acids : 5-5′,8′-O-4″-Triferulic acid
Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)

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