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Adipic acid

Alias: Adipic acid NSC7622 NSC 7622 NSC-7622
Cat No.:V5428 Purity: ≥98%
Adipic acid has been found to be associated with HMG-CoA lyase deficiency, carnitine kinase deficiency, and medium-chain acyl dehydrogenase deficiency, all of which are caused by innate metabolic abnormalities.
Adipic acid
Adipic acid Chemical Structure CAS No.: 124-04-9
Product category: New15
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Adipic acid:

  • Adipic acid-d10 (adipic acid-d10; fat acid-d10)
  • Adipic acid-13C6 (adipic acid-13C6; fat acid-13C6)
  • Adipic acid-d4 (adipic acid-d4; fat acid-d4)
  • Adipic acid-d4-1 (adipic acid-d4-1; fat acid-d4-1)
  • Adipic acid-13C2
  • Adipic acid-13C (adipic acid-13C; fat acid-13C)
  • Adipic acid-d8 (adipic acid-d8; fat acid-d8)
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Product Description
Adipic acid has been found to be associated with HMG-CoA lyase deficiency, carnitine kinase deficiency, and medium-chain acyl dehydrogenase deficiency, all of which are caused by innate metabolic abnormalities.
Biological Activity I Assay Protocols (From Reference)
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Absorbed adipic acid is primarily excreted in the urine unchanged or in the breath of carbon dioxide.
In man following ingestion, adipic acid is only partially metabolized; the balance is eliminated unchanged in the urine.
Metabolism / Metabolites
Radioactive adipic acid was fed to fasted experimental rats and the metabolic products identified in the urine were urea, glutamic acid, lactic acid, beta-ketoadipic acid, and citric acid. The presence of beta-ketoadipic acid provided some evidence that adipic acid is metabolized by beta-oxidation in much the same fashion as fatty acids. Further evidence was provided by the appearance of succinate in the urine of rats fed radioactive (14)C-adipic acid and injected with malonic acid. The presence of radioactive acetyl-gamma-phenyl-alphaaminobutyric acid after feeding gamma-phenyl-alpha-aminobutyric acid and (14)C-labeled adipic acid provided very strong evidence that acetate is a metabolite of adipic acid. Radioactive glycogen was isolated following feeding of glucose and radioactive adipic acid.
Adipic acid is metabolized via beta-oxidation to succinic and acetic acids, and subsequently to other normal intermediary metabolites.
Toxicity/Toxicokinetics
Toxicity Summary
IDENTIFICATION AND USE: Adipic acid is white crystalline solid. The major markets for adipic acid include use as feedstocks for nylon 6,6 resins and fibers, polyester polyols and plasticzers. Nylon 6,6 fibers and engineering resins accounted for approximately 85% of total adipic acid consumption in 2011. Polyester polyols and plasticizers, which combined accounted for 24-32% of global adipic acid consumption in 2010 . Other applications documented for adipic acid are as a lubricant additive in coatings, and foams, and in shoe soles, as tanning agent in leather industry, pH regulator in processes such as in the production of cleaning agents, pelletizing agent in disinfectant pills for drinking water, additive in flue gas sulfurization, in the coating of dishwashing machine tablets and as an additive in chemicals. Adipic acid has been identified as being used in hydraulic fracturing as a gelling agent. HUMAN EXPOSURE AND TOXICITY: Adipic acid exhibits an asthma hazard index of 0.75 using the chemical asthma hazard assessment program. Substances with indices of >0.5 have a high probability of being an asthmagen. Threshold for irritation of the human eye was 20 mg/cu m. ANIMAL STUDIES: Adipic acid is slightly toxic on acute exposure but produces moderate to severe eye irritation in rabbits (20 mg/24 hr). High concentrations of adipic acid can cause persistent pulmonary structural and functional alterations. In both mice and rabbits, lethal doses produce signs of inactivity, stomach and intestinal distention, and irritation and hemorrhage of the intestines. A group of mice received intravaginally, three time weekly, applications of a powdered mixture containing urea, adipic acid, and carboxymethyl cellulose. There was a high incidence of vaginal cancer after prolonged treatment. Experiments extended over one year, in which the three ingredients were given separately, yielded no tumors. Adipic acid is not mutagenic in Salmonella typhimurium strains TA98, TA100, TA1535, TA1537, and TA1538 or in Escherichia coli (WP2(uvrA)) with or without rat microsomal activation. ECOTOXICITY STUDIES: Adipic acid is slightly to moderately toxic to fish, daphnia, and algae in acute tests.
Interactions
A group of mice received intravaginally, three time weekly, applications of a powdered mixture containing urea, adipic acid, and carboxymethyl cellulose. There was a high incidence of vaginal cancer after prolonged treatment. Experiments extended over one year, in which the three ingredients were given separately, yielded no tumors.
Non-Human Toxicity Values
Rat: inhalation: no effect level: 126 g/L, 15 x 6 hr (as in source)
LD50 Mouse iv 680 mg/kg /From table/
LD50 Mouse oral 1900 mg/kg /From table/
LD50 Mouse ip 275 mg/kg /From table/
For more Non-Human Toxicity Values (Complete) data for ADIPIC ACID (8 total), please visit the HSDB record page.
References

[1]. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center. METAGENE consortium.

Additional Infomation
Adipic acid is a white crystalline solid. It is insoluble in water. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. It is used to make plastics and foams and for other uses.
Adipic acid is an alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane. It has a role as a food acidity regulator and a human xenobiotic metabolite. It is an alpha,omega-dicarboxylic acid and a dicarboxylic fatty acid. It is a conjugate acid of an adipate(1-).
Adipic Acid has been reported in Drosophila melanogaster, Populus tremula, and other organisms with data available.
See also: Polyester-10 (monomer of); Polyester-7 (monomer of); Adipic acid/diglycol crosspolymer (20000 MPA.S) (monomer of) ... View More ...
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H10O4
Molecular Weight
146.14
Exact Mass
146.057
CAS #
124-04-9
Related CAS #
Adipic acid-d10;25373-21-1;Adipic acid-13C6;942037-55-0;Adipic acid-d4;121311-78-2;Adipic acid-13C;2708283-72-9;Adipic acid-d8;52089-65-3;Adipic acid-d4-1;19031-55-1
PubChem CID
196
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
338.5±15.0 °C at 760 mmHg
Melting Point
151-154 °C(lit.)
Flash Point
196 ºC
Vapour Pressure
0.0±1.6 mmHg at 25°C
Index of Refraction
1.476
LogP
0.08
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
5
Heavy Atom Count
10
Complexity
114
Defined Atom Stereocenter Count
0
InChi Key
WNLRTRBMVRJNCN-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
Chemical Name
hexanedioic acid
Synonyms
Adipic acid NSC7622 NSC 7622 NSC-7622
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)
DMSO : ~100 mg/mL (~684.28 mM)
H2O : ~2.86 mg/mL (~19.57 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (17.11 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (17.11 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (17.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 25 mg/mL (171.07 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.8428 mL 34.2138 mL 68.4275 mL
5 mM 1.3686 mL 6.8428 mL 13.6855 mL
10 mM 0.6843 mL 3.4214 mL 6.8428 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
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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:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • 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.

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  • 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.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT01991574 COMPLETED Drug: Calcium acetate
Dietary Supplement: Iron Hydroxide Adipate
Drug: Placebo
Chronic Kidney Diseases
Healthy
Medical Research Council 2009-04 Early Phase 1
NCT04305249 RECRUITING Drug: ATG-017
Drug: ATG-017+Nivolumab
Hematological Malignancy
Solid Tumor
Antengene Therapeutics Limited 2020-08-15 Phase 1
NCT06285799 RECRUITING Drug: Low Dose IHAT
Drug: High Dose IHAT
Drug: Carob Flour
Iron-deficiency Nemysis Ltd 2024-03-05 Phase 3
NCT04239989 ACTIVE, NOT RECRUITING Drug: Itacitinib
Drug: Itacitinib Adipate
Bronchiolitis Obliterans M.D. Anderson Cancer Center 2021-04-08 Phase 1
NCT04200365 TERMINATED Drug: Itacitinib Chronic Graft-versus-host-disease SCRI Development Innovations, LLC 2020-06-05 Phase 2
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