Feruloyltyramine | CAS#80510-09-4

MedKoo Cat#: 534648 | Name: N-cis-Feruloyl tyramine

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Description:

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

N-cis-Feruloyl tyramine (cis-N-(4-Hydroxyphenethyl) ferulamide) is a natural phenolic compound, exhibits modest inhibitory activity on LPS-activated. Note: Alfrutamide is an trans-isomer (E-isomer with CAS#66648-43-9 and 65646-26-6) and N-cis-Feruloyl tyramine is a cis-isomer (Z-isomer, with CAS#80510-09-4)

Chemical Structure

N-cis-Feruloyl tyramine

CAS#80510-09-4 (Z-isomer)

Theoretical Analysis

MedKoo Cat#: 534648

Name: N-cis-Feruloyl tyramine

CAS#: 80510-09-4 (Z-isomer)

Chemical Formula: C18H19NO4

Exact Mass: 313.1314

Molecular Weight: 313.35

Elemental Analysis: C, 69.00; H, 6.11; N, 4.47; O, 20.42

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 750.00	2 Weeks

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Related CAS #

66648-43-9 (E-isomer) 65646-26-6 (E-isomer) 80510-09-4 (Z-isomer)

Synonym

Feruloyltyramine; N-cis-Feruloyl tyramine;

IUPAC/Chemical Name

(Z)-3-(4-hydroxy-3-methoxyphenyl)-N-(4-hydroxyphenethyl)acrylamide

InChi Key

NPNNKDMSXVRADT-UITAMQMPSA-N

InChi Code

InChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5-

SMILES Code

OC(C=C1)=CC=C1CCNC(/C=C\C2=CC(OC)=C(C=C2)O)=O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 313.35 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

1: King RR, Calhoun LA. A feruloyltyramine trimer isolated from potato common scab lesions. Phytochemistry. 2010 Dec;71(17-18):2187-9. doi: 10.1016/j.phytochem.2010.09.020. Epub 2010 Oct 26. PMID: 21030053. 2: Gao X, Wang C, Chen Z, Chen Y, Santhanam RK, Xue Z, Ma Q, Guo Q, Liu W, Zhang M, Chen H. Effects of N-trans-feruloyltyramine isolated from laba garlic on antioxidant, cytotoxic activities and H2O2-induced oxidative damage in HepG2 and L02 cells. Food Chem Toxicol. 2019 Aug;130:130-141. doi: 10.1016/j.fct.2019.05.021. Epub 2019 May 16. PMID: 31103739. 3: Xia Z, Xu TQ, Xu W, Zhang HX, Liang QP, Zhou GX. Lyciyunin, a new dimer of feruloyltyramine and five bioactive tyramines from the root of Lycium yunnanense Kuang. Nat Prod Res. 2019 Jul 8:1-8. doi: 10.1080/14786419.2019.1636375. Epub ahead of print. PMID: 31282219. 4: Xu S, Liu Y, Xiang L, Zhou F, Li H, Su Y, Xu X, Wang Q. Metabolites Identification of Bioactive Compounds Daturataturin A, Daturametelin I, N-Trans-Feruloyltyramine, and Cannabisin F From the Seeds of Datura metel in Rats. Front Pharmacol. 2018 Jul 9;9:731. doi: 10.3389/fphar.2018.00731. PMID: 30050436; PMCID: PMC6052896. 5: Efdi M, Ohguchi K, Akao Y, Nozawa Y, Koketsu M, Ishihara H. N-trans- feruloyltyramine as a melanin biosynthesis inhibitor. Biol Pharm Bull. 2007 Oct;30(10):1972-4. doi: 10.1248/bpb.30.1972. PMID: 17917275. 6: Jiang Y, Yu L, Wang MH. N-trans-feruloyltyramine inhibits LPS-induced NO and PGE2 production in RAW 264.7 macrophages: Involvement of AP-1 and MAP kinase signalling pathways. Chem Biol Interact. 2015 Jun 25;235:56-62. doi: 10.1016/j.cbi.2015.03.029. Epub 2015 Apr 2. PMID: 25843058. 7: Park JB. Isolation and characterization of N-feruloyltyramine as the P-selectin expression suppressor from garlic (Allium sativum). J Agric Food Chem. 2009 Oct 14;57(19):8868-72. doi: 10.1021/jf9018382. PMID: 19807156. 8: Thangnipon W, Suwanna N, Kitiyanant N, Soi-Ampornkul R, Tuchinda P, Munyoo B, Nobsathian S. Protective role of N-trans-feruloyltyramine against β-amyloid peptide-induced neurotoxicity in rat cultured cortical neurons. Neurosci Lett. 2012 Apr 4;513(2):229-32. doi: 10.1016/j.neulet.2012.02.047. Epub 2012 Feb 24. PMID: 22387154. 9: Yamamoto I, Matsunaga T, Kobayashi H, Watanabe K, Yoshimura H. Analysis and pharmacotoxicity of feruloyltyramine as a new constituent and p-coumaroyltyramine in Cannabis sativa L. Pharmacol Biochem Behav. 1991 Nov;40(3):465-9. doi: 10.1016/0091-3057(91)90348-6. PMID: 1806939. 10: Kim Y, Lee S, Ryu JH, Yoon KD, Shin SS. Effect of Aurea Helianthus stem extract on anti-melanogenesis. Biosci Biotechnol Biochem. 2018 Nov;82(11):1871-1879. doi: 10.1080/09168451.2018.1506311. Epub 2018 Aug 25. PMID: 30146944.