N-Caffeoyltyramine

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MedKoo CAT#: 462739

CAS#: 103188-48-3

Description: 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.


Price and Availability

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Pricing updated 2020-10-30. Prices are subject to change without notice.

N-Caffeoyltyramine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, SDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 462739
Name: N-Caffeoyltyramine
CAS#: 103188-48-3
Chemical Formula: C17H17NO4
Exact Mass: 299.1158
Molecular Weight: 299.326
Elemental Analysis: C, 68.22; H, 5.72; N, 4.68; O, 21.38


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


Technical Data

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


References

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.