WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H540291
CAS#: 3843-74-1
Description: Methyl caffeate is an α-glucosidase inhibitor found in species of Solanum and Magnolia. It exhibits several biological activities, including suppressing growth of Pseudomonas, Klebsiella, and Mycobacterium, inhibiting replication of HIV, and decreasing blood glucose levels in models of diabetes.
Hodoodo Cat#: H540291
Name: Methyl caffeate
CAS#: 3843-74-1
Chemical Formula: C10H10O4
Exact Mass: 194.06
Molecular Weight: 194.186
Elemental Analysis: C, 61.85; H, 5.19; O, 32.96
Synonym: Caffeic acid, methyl ester; Methyl caffeate
IUPAC/Chemical Name: methyl (E)-3-(3,4-dihydroxyphenyl)acrylate
InChi Key: OCNYGKNIVPVPPX-HWKANZROSA-N
InChi Code: 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+
SMILES Code: O=C(OC)/C=C/C1=CC=C(O)C(O)=C1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 194.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Balachandran C, Emi N, Arun Y, Yamamoto Y, Ahilan B, Sangeetha B, Duraipandiyan V, Inaguma Y, Okamoto A, Ignacimuthu S, Al-Dhabi NA, Perumal PT. In vitro anticancer activity of methyl caffeate isolated from Solanum torvum Swartz. fruit. Chem Biol Interact. 2015 Dec 5;242:81-90. doi: 10.1016/j.cbi.2015.09.023. Epub 2015 Sep 28. PubMed PMID: 26415618.
2: Pan CH, Lin WH, Chien YC, Liu FC, Sheu MJ, Kuo YH, Wu CH. K20E, an oxidative-coupling compound of methyl caffeate, exhibits anti-angiogenic activities through down-regulations of VEGF and VEGF receptor-2. Toxicol Appl Pharmacol. 2015 Jan 15;282(2):215-26. doi: 10.1016/j.taap.2014.11.009. Epub 2014 Dec 4. PubMed PMID: 25481497.
3: Bailly F, Toillon RA, Tomavo O, Jouy N, Hondermarck H, Cotelle P. Antiproliferative and apoptotic effects of the oxidative dimerization product of methyl caffeate on human breast cancer cells. Bioorg Med Chem Lett. 2013 Jan 15;23(2):574-8. doi: 10.1016/j.bmcl.2012.11.009. Epub 2012 Nov 22. PubMed PMID: 23228470.
4: Balachandran C, Duraipandiyan V, Al-Dhabi NA, Balakrishna K, Kalia NP, Rajput VS, Khan IA, Ignacimuthu S. Antimicrobial and Antimycobacterial Activities of Methyl Caffeate Isolated from Solanum torvum Swartz. Fruit. Indian J Microbiol. 2012 Dec;52(4):676-81. doi: 10.1007/s12088-012-0313-8. Epub 2012 Oct 9. PubMed PMID: 24293730; PubMed Central PMCID: PMC3516656.
5: Pang N, Gu SS, Wang J, Cui HS, Wang FQ, Liu X, Zhao XY, Wu FA. A novel chemoenzymatic synthesis of propyl caffeate using lipase-catalyzed transesterification in ionic liquid. Bioresour Technol. 2013 Jul;139:337-42. doi: 10.1016/j.biortech.2013.04.057. Epub 2013 Apr 22. PubMed PMID: 23665696.
6: Gandhi GR, Ignacimuthu S, Paulraj MG, Sasikumar P. Antihyperglycemic activity and antidiabetic effect of methyl caffeate isolated from Solanum torvum Swartz. fruit in streptozotocin induced diabetic rats. Eur J Pharmacol. 2011 Nov 30;670(2-3):623-31. doi: 10.1016/j.ejphar.2011.09.159. Epub 2011 Sep 24. PubMed PMID: 21963451.
7: Takahashi K, Yoshioka Y, Kato E, Katsuki S, Iida O, Hosokawa K, Kawabata J. Methyl caffeate as an alpha-glucosidase inhibitor from Solanum torvum fruits and the activity of related compounds. Biosci Biotechnol Biochem. 2010;74(4):741-5. Epub 2010 Apr 7. PubMed PMID: 20378981.
8: Masuda T, Yamada K, Akiyama J, Someya T, Odaka Y, Takeda Y, Tori M, Nakashima K, Maekawa T, Sone Y. Antioxidation mechanism studies of caffeic acid: identification of antioxidation products of methyl caffeate from lipid oxidation. J Agric Food Chem. 2008 Jul 23;56(14):5947-52. doi: 10.1021/jf800781b. Epub 2008 Jun 18. PubMed PMID: 18558705.
9: Lim H, Park BK, Shin SY, Kwon YS, Kim HP. Methyl caffeate and some plant constituents inhibit age-related inflammation: effects on senescence-associated secretory phenotype (SASP) formation. Arch Pharm Res. 2017 Apr;40(4):524-535. doi: 10.1007/s12272-017-0909-y. Epub 2017 Mar 15. PubMed PMID: 28299617.
10: Fujimoto A, Inai M, Masuda T. Chemical evidence for the synergistic effect of a cysteinyl thiol on the antioxidant activity of caffeic and dihydrocaffeic esters. Food Chem. 2013 Jun 1;138(2-3):1483-92. doi: 10.1016/j.foodchem.2012.11.073. Epub 2012 Nov 24. PubMed PMID: 23411271.
11: Wang J, Gu SS, Cui HS, Yang LQ, Wu XY. Rapid synthesis of propyl caffeate in ionic liquid using a packed bed enzyme microreactor under continuous-flow conditions. Bioresour Technol. 2013 Dec;149:367-74. doi: 10.1016/j.biortech.2013.09.098. Epub 2013 Sep 29. PubMed PMID: 24128399.
12: Inayama S, Harimaya K, Hori H, Ohkura T, Kawamata T, Hikichi M, Yokokura T. Studies on non-sesquiterpenoid constituents of Gaillardia pulchella. II. Less lipophilic substances, methyl caffeate as an antitumor catecholic. Chem Pharm Bull (Tokyo). 1984 Mar;32(3):1135-41. PubMed PMID: 6744486.
13: Khan RS, Senthi M, Rao PC, Basha A, Alvala M, Tummuri D, Masubuti H, Fujimoto Y, Begum AS. Cytotoxic constituents of Abutilon indicum leaves against U87MG human glioblastoma cells. Nat Prod Res. 2015;29(11):1069-73. doi: 10.1080/14786419.2014.976643. Epub 2014 Nov 25. PubMed PMID: 25422029.
14: Wang J, Gu SS, Cui HS, Wu XY, Wu FA. A novel continuous flow biosynthesis of caffeic acid phenethyl ester from alkyl caffeate and phenethanol in a packed bed microreactor. Bioresour Technol. 2014 Apr;158:39-47. doi: 10.1016/j.biortech.2014.01.145. Epub 2014 Feb 10. PubMed PMID: 24583213.
15: Fujimoto A, Masuda T. Chemical interaction between polyphenols and a cysteinyl thiol under radical oxidation conditions. J Agric Food Chem. 2012 May 23;60(20):5142-51. doi: 10.1021/jf3008822. Epub 2012 May 14. PubMed PMID: 22551224.
16: Esteban-Torres M, Reverón I, Mancheño JM, de Las Rivas B, Muñoz R. Characterization of a feruloyl esterase from Lactobacillus plantarum. Appl Environ Microbiol. 2013 Sep;79(17):5130-6. doi: 10.1128/AEM.01523-13. Epub 2013 Jun 21. PubMed PMID: 23793626; PubMed Central PMCID: PMC3753946.
17: Qu ZY, Zhang YW, Zheng SW, Yao CL, Jin YP, Zheng PH, Sun CH, Wang YP. A new phenylethanoid glycoside from Orobanche cernua Loefling. Nat Prod Res. 2016;30(8):948-53. doi: 10.1080/14786419.2015.1084305. Epub 2015 Sep 10. PubMed PMID: 26358786.
18: Kicel A, Wolbiś M. Study on the phenolic constituents of the flowers and leaves of Trifolium repens L. Nat Prod Res. 2012 Nov;26(21):2050-4. Epub 2011 Nov 25. PubMed PMID: 22117193.
19: Zhang SB, Zhai HC, Wang L, Yu GH. Expression, purification and characterization of a feruloyl esterase A from Aspergillus flavus. Protein Expr Purif. 2013 Nov;92(1):36-40. doi: 10.1016/j.pep.2013.08.009. Epub 2013 Aug 25. PubMed PMID: 23981381.
20: Zheng W, Lu X, Fu Z, Zhang L, Li X, Xu X, Ren Y, Lu Y, Fu H, Tian J. Identification of candidate synovial membrane biomarkers after Achyranthes aspera treatment for rheumatoid arthritis. Biochim Biophys Acta. 2016 Mar;1864(3):308-16. doi: 10.1016/j.bbapap.2015.12.010. Epub 2015 Dec 24. PubMed PMID: 26724776.
