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Furosine dihydrochloride

Cat No.:V68226 Purity: ≥98%
Furosine di-HCl is an amino acid (AA) analogue and an important chemical marker of the early Maillard reaction.
Furosine dihydrochloride
Furosine dihydrochloride Chemical Structure CAS No.: 157974-36-2
Product category: Amino Acid Derivatives
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
Other Sizes
Official Supplier of:
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Product Description
Furosine di-HCl is an amino acid (AA) analogue and an important chemical marker of the early Maillard reaction. Furosine di-HCl is closely associated with many diseases including diabetes.
Furosine dihydrochloride (CAS#: 157974-36-2), also known as N⁶-[2-(2-furyl)-2-oxoethyl]-L-lysine dihydrochloride, is an amino acid derivative formed by the Maillard reaction between reducing sugars and the ε-amino group of lysine. With a molecular formula of C₁₂H₂₀Cl₂N₂O₄ and a molecular weight of 327.20 g/mol, it appears as an off-white to light yellow solid powder. Furosine serves as an important chemical marker for monitoring early-stage Maillard reactions in food processing and biological samples. The compound is closely associated with various pathological conditions including diabetes. It is primarily used as an analytical standard for detecting protein glycation in food quality assessment and biological research. Furosine gradually degrades into various advanced glycation end products (AGEs), some of which are proven to be significantly associated with multiple diseases. The compound is typically stored as a powder at -20°C for long-term stability (up to 3 years) and at 4°C for up to 2 years. It is soluble in DMSO, methanol, and water. The compound's chemical structure includes 5 hydrogen bond donors, 6 hydrogen bond acceptors, 9 rotatable bonds, and 1 defined atom stereocenter. Furosine has been found in high-temperature milk and microwaved cookies, indicating its formation during thermal processing of foods.
Biological Activity I Assay Protocols (From Reference)
Targets
Furosine dihydrochloride functions as a marker compound rather than a drug with a defined therapeutic target. Its biological relevance stems from its formation as a product of the Maillard reaction, which is implicated in the pathogenesis of diabetes and other age-related diseases. The compound's "target" in research contexts is the detection and quantification of early glycation products. In cell-based studies, furosine has been shown to induce cell cycle arrest at the S phase in HEK293 and HepG2 cells at a concentration of 200 µM, indicating its potential to interfere with cellular proliferation. However, it is not a pharmacological agent designed to modulate specific receptors or enzymes. Furosine is closely associated with many diseases including diabetes, and having a high concentration of AGEs in the body is considered harmful. The compound may break down gradually to produce a wide variety of advanced glycation end products (AGEs). Fingernail levels of furosine are increased in patients with diabetes mellitus, suggesting its potential as a non-invasive biomarker for monitoring glycation status in diabetic patients.
ln Vitro
Furosine may break down gradually to produce a wide variety of advanced glycation end products (AGEs). It has been demonstrated that several AGEs are strongly linked to a number of illnesses, including diabetes, and that having a high concentration of AGEs in the body is harmful[1].
In vitro activity studies have demonstrated that furosine dihydrochloride induces cell cycle arrest at the S phase in HEK293 and HepG2 cells. The compound has been investigated for its role in various disease models, particularly diabetes, where it serves as a biomarker of protein glycation. As an amino acid analogue, furosine may interfere with normal lysine metabolism and protein function. However, the compound is primarily studied as a marker rather than for its intrinsic biological activity. Its presence in biological samples correlates with the extent of Maillard reaction products, making it a valuable indicator of advanced glycation end-product formation. In vitro assays typically involve the use of furosine as a reference standard in HPLC or LC-MS methods for quantifying Maillard reaction products. The compound's activity is assessed through its concentration measurements rather than through traditional pharmacological activity assays. Furosine has been shown to gradually degrade into various advanced glycation end products (AGEs), some of which are proven to be significantly associated with multiple diseases including diabetes.
ln Vivo
In vivo activity of furosine dihydrochloride has not been extensively characterized as the compound is primarily used as an analytical standard and research reagent. It is not administered as a therapeutic agent in animal models. Studies have linked furosine levels to diabetes and related complications, suggesting that its accumulation in vivo may reflect underlying pathological processes. Furosine (500 mg/kg per day) has been reported to increase testicular atrophy and decrease testosterone levels in mice, indicating potential endocrine effects at high doses. However, these associations are observational rather than causative. The compound's role in disease is as a biomarker rather than an active pharmacological entity, and no established in vivo efficacy models exist for this compound. The compound is not intended for administration to animals as a therapeutic or investigative agent. Its primary application is as an analytical standard in food chemistry and glycation research.
Enzyme Assay
The in vitro enzyme/receptor binding (non-cellular) experimental workflow for furosine dihydrochloride typically involves analytical chemistry procedures rather than binding assays. The compound is used as a reference standard in HPLC or LC-MS methods for quantifying Maillard reaction products in food and biological samples. A typical workflow includes preparing standard solutions of furosine dihydrochloride at various concentrations (typically 0.5-50 µg/mL in 0.1% formic acid), establishing calibration curves, and analyzing samples after acid hydrolysis to release bound furosine. Detection is commonly performed using UV absorbance at 280 nm or mass spectrometry. Method validation includes assessment of linearity (R²>0.999), limit of detection (~0.1 µg/mL), precision, accuracy, and recovery (95-105%). Acid hydrolysis of food/protein samples (6N HCl, 110°C, 24 hours) releases furosine for quantification. The compound's solubility data indicates it may dissolve in DMSO, and if not, other solvents such as H₂O, ethanol, or DMF can be tried. The compound is stable at ambient temperature for a few days during ordinary shipping.
Cell Assay
In vitro cell-based experimental workflows involving furosine dihydrochloride are limited but have been reported. One reported study used HEK293 and HepG2 cells to investigate the compound's effect on cell cycle progression at a concentration of 200 µM. In such assays, cells are cultured in appropriate medium (typically DMEM with 10% FBS), treated with varying concentrations of furosine dihydrochloride (0-200 µM) for 24 hours, and analyzed for cell cycle distribution using flow cytometry after propidium iodide staining. Other potential assays might include assessment of cell viability (MTT assay), apoptosis detection (Annexin V staining), or measurement of oxidative stress markers. However, these are not standard protocols for this compound, as it is primarily an analytical standard. The compound's primary value in cell-based research is as a marker of glycation rather than as a biologically active compound.
Animal Protocol
In vivo animal experimental workflows are not established for furosine dihydrochloride as a test compound. The compound is not intended for administration to animals as a therapeutic or investigative agent. Its primary application is as an analytical standard in food chemistry and glycation research. While animal models of diabetes might be used to measure furosine levels as a biomarker of glycation, the compound itself is not the subject of in vivo efficacy studies. In diabetic rodent models, plasma or tissue furosine levels are measured as a biomarker after induction (e.g., streptozotocin). Blood samples are collected, hydrolyzed, and analyzed by LC-MS. The compound is stored as a powder at -20°C for long-term stability. In vivo formulation calculators may be used for preparing solutions if animal studies were to be conducted, but such studies are not standard for this compound.
ADME/Pharmacokinetics
The pharmacokinetic properties of furosine dihydrochloride have not been systematically characterized, as the compound is not a drug candidate. Given its structural similarity to lysine, it might be expected to be absorbed and metabolized through amino acid pathways if ingested. However, furosine is formed endogenously through glycation reactions and is primarily studied as a biomarker rather than an administered compound. No data on absorption, distribution, metabolism, or excretion are available in the literature. The compound is stable under recommended storage conditions: powder at -20°C for 3 years, 4°C for 2 years; in solvent at -80°C for 6 months or -20°C for 1 month. The compound is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs. The compound's solubility in various solvents has been characterized, with solubility in DMSO, methanol, and water reported.
Toxicity/Toxicokinetics
The toxicological data for furosine dihydrochloride are not well-documented, as it is not a pharmaceutical product. Standard laboratory safety practices should be followed when handling this compound. As a Maillard reaction product, furosine is associated with the formation of advanced glycation end products (AGEs), which are considered harmful and linked to various diseases including diabetes. However, the compound itself is not classified as acutely toxic. It is intended for research use only and is not for human use. The compound should be handled with appropriate personal protective equipment including gloves and safety glasses. No chronic toxicity, carcinogenicity, or reproductive toxicity studies have been conducted, as these are not relevant for an analytical standard. The compound is not approved for human or veterinary applications.
References
[1]. Li Y, et, al. Qualitative and quantitative analysis of furosine in fresh and processed ginsengs. J Ginseng Res. 2018 Jan;42(1):21-26.
[2]. Poojary MM, et, al. Liquid chromatography quadrupole-Orbitrap mass spectrometry for the simultaneous analysis of advanced glycation end products and protein-derived cross-links in food and biological matrices. J Chromatogr A. 2020 Mar 29;1615:460767.
Additional Infomation
Furosine dihydrochloride is a widely used analytical standard in food chemistry and glycation research. It is not a drug and has no clinical trials or approvals. It serves as a quality marker for heat-processed foods and is studied in relation to diabetic complications. The compound 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 (500 mg/kg per day) has been reported to increase testicular atrophy and decrease testosterone levels in mice. Fingernail levels of furosine are increased in patients with diabetes mellitus. It has been found in high-temperature milk and microwaved cookies. The compound is available from multiple suppliers in various pack sizes (1 mg, 5 mg, etc.). Sample solutions are provided at 25 µL, 10 mM. The compound is typically stored at -20°C.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H20CL2N2O4
Molecular Weight
327.20
Exact Mass
326.08
CAS #
157974-36-2
PubChem CID
92043346
Appearance
Off-white to light yellow solid powder
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
9
Heavy Atom Count
20
Complexity
283
Defined Atom Stereocenter Count
1
SMILES
C1=COC(=C1)C(=O)CNCCCC[C@@H](C(=O)O)N.Cl
InChi Key
UWZJNJSUGNECAN-FVGYRXGTSA-N
InChi Code
InChI=1S/C12H18N2O4.ClH/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);1H/t9-;/m0./s1
Chemical Name
(2S)-2-amino-6-[[2-(furan-2-yl)-2-oxoethyl]amino]hexanoic acid;hydrochloride
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0562 mL 15.2812 mL 30.5623 mL
5 mM 0.6112 mL 3.0562 mL 6.1125 mL
10 mM 0.3056 mL 1.5281 mL 3.0562 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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