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Perfluoroundecanoic acid

Alias: Perfluoroundecanoic acid; Heneicofluoroundecanoic acid
Perfluoroundecanoic acid is an orally active inducer of oxidative stress and DNA damage.
Perfluoroundecanoic acid
Perfluoroundecanoic acid Chemical Structure CAS No.: 2058-94-8
Product category: Biochemical Assay Reagents
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
Other Sizes
Official Supplier of:
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Product Description
Perfluoroundecanoic acid is an orally active inducer of oxidative stress and DNA damage. Perfluoroundecanoic acid exerts genotoxic and reproductive toxicity in Swiss mice. Perfluoroundecanoic acid is used as a processing aid in the manufacture of fluoropolymers because of its thermal and pressure stability and the properties of having both water- and oil-repellent groups and hydrophilic groups on the same molecule.
Perfluoroundecanoic acid (PFUnDA) is a perfluorinated carboxylic acid with the molecular formula C11HF21O2 and a molecular weight of 564.09 g/mol. It consists of a fully fluorinated carbon chain of eleven carbon atoms, imparting unique chemical and physical properties. It appears as a solid at 20degC with a melting point of 96-101degC. This compound is used as a processing aid in the manufacture of fluoropolymers and as an analytical standard.
Biological Activity I Assay Protocols (From Reference)
Targets
Perfluoroundecanoic acid is an orally active inducer of oxidative stress and DNA damage, exerting genotoxic and reproductive toxicity in Swiss mice. It is not a drug but an environmental contaminant and industrial chemical. It is known to activate the peroxisome proliferator-activated receptor alpha (PPARalpha) and may disrupt endocrine function. Its "target" in toxicology studies includes the liver, testis, and other organs.
ln Vitro
Perfluoroundecanoic acid induces oxidative stress and DNA damage in vitro, although specific IC50 values are not provided. In Swiss mice, it exerts genotoxic and reproductive toxicity. It is known to be toxic to the liver and has been associated with reproductive and developmental toxicity in animal studies. It is used as a standard in analytical chemistry to monitor environmental and biological samples.
ln Vivo
Perfluoroundecanoic acid is an orally active toxicant in animals. In Swiss mice, it exerts genotoxic effects and reproductive toxicity. Chronic exposure to perfluorinated compounds (PFCs) has been linked to liver toxicity, immune suppression, and developmental effects in various animal models. PFUnDA, as a long-chain PFC, is known to persist in the body and cause bioaccumulation.
Enzyme Assay
Not applicable. Perfluoroundecanoic acid is not used in cell-free enzyme assays as a substrate or inhibitor. It is an industrial chemical and environmental contaminant. Its activity is assessed in vivo or in cell culture systems. For analytical purposes, it is quantified by LC-MS/MS. For receptor binding studies, it can be used to assess PPARalpha activation using a reporter gene assay.
Cell Assay
The toxicological effects of Perfluoroundecanoic acid can be assessed in hepatocytes. Procedure: Primary mouse hepatocytes are isolated via collagenase perfusion and seeded in 6-well plates (1×10⁶ cells/well). Cells are treated with varying concentrations of Perfluoroundecanoic acid (1-500 uM) for 24-48 hours. Cellular reactive oxygen species (ROS) levels are measured using DCFH-DA fluorescent dye. DNA damage is assessed by the comet assay (single-cell gel electrophoresis). Cell viability is measured by MTT assay. The EC50 for cytotoxicity or ROS induction is calculated.
Animal Protocol
The in vivo toxicity of Perfluoroundecanoic acid can be evaluated in a mouse model. Procedure: Male Swiss mice (8 weeks, n=10 per group) are administered Perfluoroundecanoic acid orally (gavage) at doses of 0, 10, 50, and 100 mg/kg daily for 28 days. Control animals receive vehicle (e.g., 0.5% Tween-80 in water). Body weight and food intake are monitored weekly. At the end of the study, mice are euthanized, and blood is collected for serum chemistry (ALT, AST, creatinine). Liver, testis, and kidney are harvested for histological analysis (H&E staining). Sperm count and morphology are assessed for reproductive toxicity. Micronucleus test is performed on bone marrow smears to assess genotoxicity.
ADME/Pharmacokinetics
Perfluoroundecanoic acid is orally active and known to bioaccumulate. In animal studies, it has a long half-life (weeks to months) and is distributed primarily to the liver, kidneys, and blood. It is not extensively metabolized and is excreted mainly in urine and feces. Due to its persistence, it accumulates in the body over time.
Toxicity/Toxicokinetics
Perfluoroundecanoic acid is toxic and has been shown to induce oxidative stress, DNA damage, genotoxicity, and reproductive toxicity in mice. It is classified as a hazardous substance and can cause liver injury, developmental toxicity, and endocrine disruption. Due to its environmental persistence and bioaccumulation, it is a pollutant of concern. Perfluoroundecanoic acid is for research use only and is not a drug.
References

[1]. Perfluoroundecanoic acid induces DNA damage, reproductive and pathophysiological dysfunctions via oxidative stress in male Swiss mice. Chemosphere. 2023 Oct;338:139491.

Additional Infomation
Perfluoroundecanoic acid is a fluoroalkyl acid, specifically perfluorinated undecanoic acid. It is an exogenous substance and environmental pollutant whose function is related to undecanoic acid. Perfluoroundecanoic acid belongs to the perfluoroalkyl acids (PFAAs). PFAAs are frequently detected in the environment, plants, fish, and animals. They are decomposition products of stain- and oil-resistant coatings on food packaging, sofas, carpets, and other surfaces. Like many PFAAs, it is persistent and bioaccumulative. PFAAs are considered endocrine disruptors, and many are known toxins and carcinogens. PFAAs have been used in the manufacture of well-known consumer products such as Teflon and Gore-Tex.
Perfluoroundecanoic acid (PFUnDA) is a perfluoroalkyl carboxylic acid (PFCA) belonging to the class of per- and polyfluoroalkyl substances (PFAS). It is used as a processing aid in the manufacture of fluoropolymers and has been detected in the environment as a persistent contaminant. PFUnDA is known to be toxic and has been shown to induce oxidative stress, DNA damage, genotoxicity, and reproductive toxicity. It is used as a reference standard for environmental and toxicological analysis. This product is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11HF21O2
Molecular Weight
564.09
Exact Mass
563.964
CAS #
2058-94-8
PubChem CID
77222
Appearance
White to off-white solid powder
Density
1.764g/cm3
Boiling Point
229.5ºC at 760 mmHg ,160ºC60 mm Hg(lit.)
Melting Point
96-101ºC(lit.)
Flash Point
92.6ºC
Vapour Pressure
0.0247mmHg at 25°C
Index of Refraction
1.288
LogP
6.351
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
23
Rotatable Bond Count
9
Heavy Atom Count
34
Complexity
789
Defined Atom Stereocenter Count
0
SMILES
FC(C(C(C(C(C(=O)O[H])(F)F)(F)F)(F)F)(F)F)(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)F
InChi Key
SIDINRCMMRKXGQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C11HF21O2/c12-2(13,1(33)34)3(14,15)4(16,17)5(18,19)6(20,21)7(22,23)8(24,25)9(26,27)10(28,29)11(30,31)32/h(H,33,34)
Chemical Name
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-henicosafluoroundecanoic acid
Synonyms
Perfluoroundecanoic acid; Heneicofluoroundecanoic acid
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 1.7728 mL 8.8638 mL 17.7277 mL
5 mM 0.3546 mL 1.7728 mL 3.5455 mL
10 mM 0.1773 mL 0.8864 mL 1.7728 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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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