Furosine HCl | CAS#157974-36-2 | Biochemical

MedKoo Cat#: 575728 | Name: Furosine HCl

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Description:

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

Furosine is an L-lysine derivative formed by the Maillard reaction and a marker of overheating in foods. It induces cell cycle arrest at the S phase in HEK293 and HepG2 cells when used at a concentration of 200 µM. Furosine triggers necroptosis in hepatocytes by regulating the RIPK1/RIPK3/MLKL pathway. Furosine induces DNA damage and cell death in selected human cell lines: a strong toxicant to kidney Hek-293 cells.

Chemical Structure

Furosine HCl

CAS#157974-36-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 575728

Name: Furosine HCl

CAS#: 157974-36-2 (HCl)

Chemical Formula: C12H20Cl2N2O4

Exact Mass: 254.1267

Molecular Weight: 327.20

Elemental Analysis: C, 44.05; H, 6.16; Cl, 21.67; N, 8.56; O, 19.56

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 Weeks
5mg	USD 750.00	2 Weeks

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Related CAS #

19746-33-9 (free base) 157974-36-2 (HCl)

Synonym

Furosine

IUPAC/Chemical Name

N6-(2-(furan-2-yl)-2-oxoethyl)-L-lysine dihydrochloride

InChi Key

HRTZJJIVKJREPV-WWPIYYJJSA-N

InChi Code

InChI=1S/C12H18N2O4.2ClH/c13-9(12(16)17)4-1-2-6-14-8-10(15)11-5-3-7-18-11;;/h3,5,7,9,14H,1-2,4,6,8,13H2,(H,16,17);2*1H/t9-;;/m0../s1

SMILES Code

N[C@@H](CCCCNCC(C1=CC=CO1)=O)C(O)=O.[H]Cl.[H]Cl

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 327.20 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: Moreno-Trujillo TR, Perez E, Verardo V, García-Villanova B, Guerra-Hernández EJ. Impact of Technological Processes on the Formation of Furosine, Acrylamide and Furan in Traditional Venezuelan Cocoa. Foods. 2024 Mar 8;13(6):829. doi: 10.3390/foods13060829. PMID: 38540818; PMCID: PMC10969732. 2: Yao GH, Ling Y, Zhang YJ, Xing SG, Yao MY, Guo W, Zhang F. [Determination of furosine in liquid milk by high performance liquid chromatography-quadrupole time-of-flight mass spectrometry]. Se Pu. 2023 Nov;41(11):1038-1043. Chinese. doi: 10.3724/SP.J.1123.2023.05009. PMID: 37968823; PMCID: PMC10654872. 3: Baskal S, Post A, Kremer D, Bollenbach A, Bakker SJL, Tsikas D. Urinary excretion of amino acids and their advanced glycation end-products (AGEs) in adult kidney transplant recipients with emphasis on lysine: furosine excretion is associated with cardiovascular and all-cause mortality. Amino Acids. 2021 Nov;53(11):1679-1693. doi: 10.1007/s00726-021-03091-8. Epub 2021 Oct 24. PMID: 34693489; PMCID: PMC8592953. 4: Li Y, Wu Y, Quan W, Jia X, He Z, Wang Z, Adhikari B, Chen J, Zeng M. Quantitation of furosine, furfurals, and advanced glycation end products in milk treated with pasteurization and sterilization methods applicable in China. Food Res Int. 2021 Feb;140:110088. doi: 10.1016/j.foodres.2020.110088. Epub 2020 Dec 29. PMID: 33648304. 5: Wang F, Zhang Y, Wen F, Zheng N, Wang J. Rapid determination of furosine in milk using microwave-assisted HCl hydrolysis and ultra-performance liquid chromatography. J Dairy Sci. 2020 Dec;103(12):11086-11093. doi: 10.3168/jds.2020-18614. Epub 2020 Oct 15. PMID: 33069412. 6: Li H, Yang H, Li P, Li M, Yao Q, Min L, Zhang Y, Wang J, Zheng N. Maillard reaction products with furan ring, like furosine, cause kidney injury through triggering ferroptosis pathway. Food Chem. 2020 Jul 30;319:126368. doi: 10.1016/j.foodchem.2020.126368. Epub 2020 Feb 6. PMID: 32155537. 7: Yu H, Zhong Q, Xie Y, Guo Y, Cheng Y, Yao W. Kinetic study on the generation of furosine and pyrraline in a Maillard reaction model system of d-glucose and l-lysine. Food Chem. 2020 Jul 1;317:126458. doi: 10.1016/j.foodchem.2020.126458. Epub 2020 Feb 20. PMID: 32109656. 8: Li H, Wang B, Yang H, Wang Y, Xing L, Chen W, Wang J, Zheng N. Furosine Posed Toxic Effects on Primary Sertoli Cells through Regulating Cep55/NF- κB/PI3K/Akt/FOX01/TNF-α Pathway. Int J Mol Sci. 2019 Jul 30;20(15):3716. doi: 10.3390/ijms20153716. PMID: 31366014; PMCID: PMC6696181. 9: Li H, Wang Y, Yang H, Zhang Y, Xing L, Wang J, Zheng N. Furosine, a Maillard Reaction Product, Triggers Necroptosis in Hepatocytes by Regulating the RIPK1/RIPK3/MLKL Pathway. Int J Mol Sci. 2019 May 14;20(10):2388. doi: 10.3390/ijms20102388. PMID: 31091743; PMCID: PMC6566718. 10: Mesías M, Sáez-Escudero L, Morales FJ, Delgado-Andrade C. Occurrence of Furosine and Hydroxymethylfurfural in Breakfast Cereals. Evolution of the Spanish Market from 2006 to 2018. Foods. 2019 May 10;8(5):158. doi: 10.3390/foods8050158. PMID: 31083379; PMCID: PMC6560387. 11: Gong RZ, Wang YH, Gao K, Zhang L, Liu C, Wang ZS, Wang YF, Sun YS. Quantification of Furosine (Nε-(2-Furoylmethyl)-l-lysine) in Different Parts of Velvet Antler with Various Processing Methods and Factors Affecting Its Formation. Molecules. 2019 Mar 31;24(7):1255. doi: 10.3390/molecules24071255. PMID: 30935092; PMCID: PMC6479359. 12: Saeed Y, Wang JQ, Zheng N. Furosine induces DNA damage and cell death in selected human cell lines: a strong toxicant to kidney Hek-293 cells. Food Sci Biotechnol. 2017 Aug 30;26(4):1093-1101. doi: 10.1007/s10068-017-0131-1. PMID: 30263641; PMCID: PMC6049533. 13: Artavia G, Rojas-Bogantes L, Granados-Chinchilla F. Two alternative chromatography methods assisted by the sulfonic acid moeity for the determination of furosine in milk. MethodsX. 2018 Jun 15;5:639-647. doi: 10.1016/j.mex.2018.06.007. PMID: 30013947; PMCID: PMC6019685. 14: Li H, Xing L, Zhao N, Wang J, Zheng N. Furosine Induced Apoptosis by the Regulation of STAT1/STAT2 and UBA7/UBE2L6 Genes in HepG2 Cells. Int J Mol Sci. 2018 May 31;19(6):1629. doi: 10.3390/ijms19061629. PMID: 29857509; PMCID: PMC6032202. 15: Li HY, Xing L, Wang JQ, Zheng N. Toxicology studies of furosine in vitro/in vivo and exploration of the related mechanism. Toxicol Lett. 2018 Jul;291:101-111. doi: 10.1016/j.toxlet.2018.02.018. Epub 2018 Feb 16. PMID: 29458171. 16: Li Y, Liu X, Meng L, Wang Y. Qualitative and quantitative analysis of furosine in fresh and processed ginsengs. J Ginseng Res. 2018 Jan;42(1):21-26. doi: 10.1016/j.jgr.2016.12.004. Epub 2017 Jan 10. PMID: 29348718; PMCID: PMC5766691. 17: Fratianni A, Niro S, Messia MC, Cinquanta L, Panfili G, Albanese D, Di Matteo M. Kinetics of carotenoids degradation and furosine formation in dried apricots (Prunus armeniaca L.). Food Res Int. 2017 Sep;99(Pt 2):862-867. doi: 10.1016/j.foodres.2016.12.009. Epub 2016 Dec 21. PMID: 28847423. 18: Troise AD, Fiore A, Wiltafsky M, Fogliano V. Quantification of Nε-(2-Furoylmethyl)-L-lysine (furosine), Nε-(Carboxymethyl)-L-lysine (CML), Nε-(Carboxyethyl)-L-lysine (CEL) and total lysine through stable isotope dilution assay and tandem mass spectrometry. Food Chem. 2015 Dec 1;188:357-64. doi: 10.1016/j.foodchem.2015.04.137. Epub 2015 Apr 30. PMID: 26041204. 19: Montilla A, Megías-Pérez R, Olano A, Villamiel M. Presence of galactooligosaccharides and furosine in special dairy products designed for elderly people. Food Chem. 2015 Apr 1;172:481-5. doi: 10.1016/j.foodchem.2014.09.079. Epub 2014 Sep 20. PMID: 25442582. 20: Giannetti V, Mariani MB, Mannino P. Furosine as a pasta quality marker: evaluation by an innovative and fast chromatographic approach. J Food Sci. 2013 Jul;78(7):C994-9. doi: 10.1111/1750-3841.12163. Epub 2013 Jun 14. PMID: 23772758.