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MedKoo Cat#: 540291 | Name: Methyl caffeate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Methyl caffeate
Methyl caffeate
CAS#3843-74-1

Theoretical Analysis

MedKoo Cat#: 540291

Name: Methyl caffeate

CAS#: 3843-74-1

Chemical Formula: C10H10O4

Exact Mass: 194.0579

Molecular Weight: 194.19

Elemental Analysis: C, 61.85; H, 5.19; O, 32.96

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
250mg USD 450.00 2 weeks
1g USD 950.00 2 Weeks
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Related CAS #
No Data
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methyl caffeate, an antimicrobial agent, shows moderate antimicrobial and prominent antimycobacterial activities.
In vitro activity:
The antimicrobial activity was screened using five Gram-positive bacteria, six Gram-negative bacteria, seven clinical isolates and four fungi. Antimycobacterial activity was screened against two Mycobacterium strains. The zone of inhibition by methyl caffeate ranged from 0 to 22 mm. The lowest minimum inhibitory concentration (MIC) values of methyl caffeate were: 50 μg/ml against P. vulgaris, 25 μg/ml against K. pneumoniae (ESBL-3971), 8 μg/ml against M. tuberculosis (H(37)Rv) and 8 μg/ml against M. tuberculosis (Rif(R)). Methyl caffeate showed moderate antimicrobial and prominent antimycobacterial activities. Reference: Indian J Microbiol. 2012 Dec;52(4):676-81. https://pubmed.ncbi.nlm.nih.gov/24293730/
In vivo activity:
Antihyperglycemic effect of methyl caffeate was studied in normal glucose-fed rats. Methyl caffeate at 40 mg/kg significantly prevented the increase in blood glucose level after glucose administration at 60 min in comparison to the hyperglycemic control group. In streptozotocin induced diabetic rats, methyl caffeate produced significant reduction in blood glucose and increased body weight. Methyl caffeate treated diabetic rats showed upregulation of GLUT4 and regeneration of β-cells in the pancreas. Reference: Eur J Pharmacol. 2011 Nov 30;670(2-3):623-31. https://pubmed.ncbi.nlm.nih.gov/21963451/
Solvent mg/mL mM comments
Solubility
DMF 5.0 25.75
DMSO 19.2 98.69
Ethanol 20.0 102.99
PBS (pH 7.2) 0.5 2.57
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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:
1. Tan FHP, Hadri NAB, Najimudin N, Watanabe N, Azzam G. Ethyl caffeate ameliorated amyloid-beta42 protein-associated toxicity in PC12 cells and Drosophila melanogaster. Geriatr Gerontol Int. 2021 Dec;21(12):1125-1130. doi: 10.1111/ggi.14296. Epub 2021 Oct 26. PMID: 34699118. 2. 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. PMID: 24293730; PMCID: PMC3516656. 3. 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. PMID: 21963451. 4. Shin KM, Kim IT, Park YM, Ha J, Choi JW, Park HJ, Lee YS, Lee KT. Anti-inflammatory effect of caffeic acid methyl ester and its mode of action through the inhibition of prostaglandin E2, nitric oxide and tumor necrosis factor-alpha production. Biochem Pharmacol. 2004 Dec 15;68(12):2327-36. doi: 10.1016/j.bcp.2004.08.002. PMID: 15548379.
In vitro protocol:
1. Tan FHP, Hadri NAB, Najimudin N, Watanabe N, Azzam G. Ethyl caffeate ameliorated amyloid-beta42 protein-associated toxicity in PC12 cells and Drosophila melanogaster. Geriatr Gerontol Int. 2021 Dec;21(12):1125-1130. doi: 10.1111/ggi.14296. Epub 2021 Oct 26. PMID: 34699118. 2. 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. PMID: 24293730; PMCID: PMC3516656.
In vivo protocol:
1. 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. PMID: 21963451. 2. Shin KM, Kim IT, Park YM, Ha J, Choi JW, Park HJ, Lee YS, Lee KT. Anti-inflammatory effect of caffeic acid methyl ester and its mode of action through the inhibition of prostaglandin E2, nitric oxide and tumor necrosis factor-alpha production. Biochem Pharmacol. 2004 Dec 15;68(12):2327-36. doi: 10.1016/j.bcp.2004.08.002. PMID: 15548379.
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.