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MedKoo Cat#: 462739 | Name: N-Caffeoyltyramine

Description:

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

N-Caffeoyltyramine is a novel phenolic amide isolated from the root bark of Lycium chinense Miller and has potent antioxidative activity and anti-fungal effects.

Chemical Structure

N-Caffeoyltyramine
N-Caffeoyltyramine
CAS#103188-48-3

Theoretical Analysis

MedKoo Cat#: 462739

Name: N-Caffeoyltyramine

CAS#: 103188-48-3

Chemical Formula: C17H17NO4

Exact Mass: 299.1158

Molecular Weight: 299.33

Elemental Analysis: C, 68.22; H, 5.72; N, 4.68; O, 21.38

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Typheramide; N-trans-Caffeoyltyramine;
IUPAC/Chemical Name
(E)-3-(3,4-dihydroxyphenyl)-N-(4-hydroxyphenethyl)acrylamide
InChi Key
VSHUQLRHTJOKTA-XBXARRHUSA-N
InChi Code
InChI=1S/C17H17NO4/c19-14-5-1-12(2-6-14)9-10-18-17(22)8-4-13-3-7-15(20)16(21)11-13/h1-8,11,19-21H,9-10H2,(H,18,22)/b8-4+
SMILES Code
Oc1ccc(CCNC(/C=C/c2cc(O)c(O)cc2)=O)cc1
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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 299.33 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
1: Olatunji OJ, Chen H, Zhou Y. Neuroprotective effect of trans-N- caffeoyltyramine from Lycium chinense against H2O2 induced cytotoxicity in PC12 cells by attenuating oxidative stress. Biomed Pharmacother. 2017 Sep;93:895-902. doi: 10.1016/j.biopha.2017.07.013. Epub 2017 Jul 13. PMID: 28715870. 2: Han EH, Kim JY, Kim HG, Choi JH, Im JH, Woo ER, Jeong HG. Dihydro-N- caffeoyltyramine down-regulates cyclooxygenase-2 expression by inhibiting the activities of C/EBP and AP-1 transcription factors. Food Chem Toxicol. 2010 Feb;48(2):579-86. doi: 10.1016/j.fct.2009.11.035. Epub 2009 Nov 14. PMID: 19922759. 3: Park JB, Schoene N. N-Caffeoyltyramine arrests growth of U937 and Jurkat cells by inhibiting protein tyrosine phosphorylation and inducing caspase-3. Cancer Lett. 2003 Dec 30;202(2):161-71. doi: 10.1016/j.canlet.2003.08.010. PMID: 14643446. 4: Ma X, Yan J, Xu K, Guo L, Li H. Binding mechanism of trans-N-caffeoyltyramine and human serum albumin: Investigation by multi-spectroscopy and docking simulation. Bioorg Chem. 2016 Jun;66:102-10. doi: 10.1016/j.bioorg.2016.04.002. Epub 2016 Apr 22. PMID: 27131098. 5: Park JB. Quantitation of clovamide-type phenylpropenoic acid amides in cells and plasma using high-performance liquid chromatography with a coulometric electrochemical detector. J Agric Food Chem. 2005 Oct 19;53(21):8135-40. doi: 10.1021/jf0516078. PMID: 16218655. 6: Xie LW, Atanasov AG, Guo DA, Malainer C, Zhang JX, Zehl M, Guan SH, Heiss EH, Urban E, Dirsch VM, Kopp B. Activity-guided isolation of NF-κB inhibitors and PPARγ agonists from the root bark of Lycium chinense Miller. J Ethnopharmacol. 2014 Mar 28;152(3):470-7. doi: 10.1016/j.jep.2014.01.029. Epub 2014 Feb 8. PMID: 24512737. 7: Xie LW, Li SX, Xie YX, Pan Y, Yu R, Cheng XH. [Bioassay-guided fractionation of constituents targeting mediators of inflammation from lycii cortex as inhibitors of NF-kappaB]. Zhongguo Zhong Yao Za Zhi. 2014 Feb;39(4):689-94. Chinese. PMID: 25204148. 8: Okombi S, Rival D, Bonnet S, Mariotte AM, Perrier E, Boumendjel A. Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte- tyrosinase. Bioorg Med Chem Lett. 2006 Apr 15;16(8):2252-5. doi: 10.1016/j.bmcl.2006.01.022. Epub 2006 Jan 26. PMID: 16442796. 9: Park JB. Caffedymine from cocoa has COX inhibitory activity suppressing the expression of a platelet activation marker, P-selectin. J Agric Food Chem. 2007 Mar 21;55(6):2171-5. doi: 10.1021/jf0628835. Epub 2007 Feb 24. PMID: 17319684. 10: Lee DG, Park Y, Kim MR, Jung HJ, Seu YB, Hahm KS, Woo ER. Anti-fungal effects of phenolic amides isolated from the root bark of Lycium chinense. Biotechnol Lett. 2004 Jul;26(14):1125-30. doi: 10.1023/B:BILE.0000035483.85790.f7. PMID: 15266117. 11: Han SH, Lee HH, Lee IS, Moon YH, Woo ER. A new phenolic amide from Lycium chinense Miller. Arch Pharm Res. 2002 Aug;25(4):433-7. doi: 10.1007/BF02976596. PMID: 12214850. 12: Yin W, Song ZR, Liu JQ, Zhang GS. [Chemical Constituents of Citrus medica Fruit]. Zhong Yao Cai. 2015 Oct;38(10):2091-4. Chinese. PMID: 27254921. 13: Affes M, Fakhfakh J, Daoud I, Brieudes V, Halabalaki M, El Feki A, Allouche N. UHPLC/HR-ESI-MS/MS Profiling of Phenolics from Tunisian Lycium arabicum Boiss. Antioxidant and Anti-lipase Activities' Evaluation. Chem Biodivers. 2017 Sep;14(9). doi: 10.1002/cbdv.201700095. Epub 2017 Aug 17. PMID: 28613438. 14: Al-Taweel AM, Perveen S, El-Shafae AM, Fawzy GA, Malik A, Afza N, Iqbal L, Latif M. Bioactive phenolic amides from Celtis africana. Molecules. 2012 Mar 5;17(3):2675-82. doi: 10.3390/molecules17032675. PMID: 22391601; PMCID: PMC6268968. 15: Park JB. Effects of typheramide and alfrutamide found in Allium species on cyclooxygenases and lipoxygenases. J Med Food. 2011 Mar;14(3):226-31. doi: 10.1089/jmf.2009.0198. PMID: 21332401. 16: Samita F, Ochieng CO, Owuor PO, Manguro LO, Midiwo JO. Isolation of a new β-carboline alkaloid from aerial parts of Triclisia sacleuxii and its antibacterial and cytotoxicity effects. Nat Prod Res. 2017 Mar;31(5):529-536. doi: 10.1080/14786419.2016.1201666. Epub 2016 Jul 3. PMID: 27373319. 17: Kim DK, Lim JP, Kim JW, Park HW, Eun JS. Antitumor and antiinflammatory constituents from Celtis sinensis. Arch Pharm Res. 2005 Jan;28(1):39-43. doi: 10.1007/BF02975133. PMID: 15742806. 18: Park JB. Identification and quantification of a major anti-oxidant and anti- inflammatory phenolic compound found in basil, lemon thyme, mint, oregano, rosemary, sage, and thyme. Int J Food Sci Nutr. 2011 Sep;62(6):577-84. doi: 10.3109/09637486.2011.562882. Epub 2011 Apr 21. PMID: 21506887. 19: Kang K, Park M, Park S, Kim YS, Lee S, Lee SG, Back K. Production of plant- specific tyramine derivatives by dual expression of tyramine N-hydroxycinnamoyltransferase and 4-coumarate:coenzyme A ligase in Escherichia coli. Biotechnol Lett. 2009 Sep;31(9):1469-75. doi: 10.1007/s10529-009-0032-3. Epub 2009 May 29. PMID: 19479321.

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OAN00639

OAN00639