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Pentanedioic acid (glutaric acid) is an organic dicarboxylic acid, widely used as a chemical intermediate in polymers, pharmaceuticals, and specialty chemicals.
Pentanedioic acid (glutaric acid)s chemical formula is C₅H₈O₄.
Pentanedioic acid (glutaric acid) belongs to the class of aliphatic dicarboxylic acids.
CAS Number: 110-94-1
Molecular Formula: C5H8O4
Molecular Weight: 132.11
EINECS Number: 203-817-2
Synonyms:2-Oxopentanedioic acid, 2-oxoglutaric acid, alpha-ketoglutaric acid, 2-oxoglutarate, Oxoglutaric acid, a-ketoglutaric acid, 2-Oxo-1,5-pentanedioic acid, Pentanedioic acid, 2-oxo-, Alphaketoglutaric acid, oxogluric acid, Glutaric acid, 2-oxo-, Glutaric acid, alpha keto, ketoglutaric acid, alpha ketoglutaric acid, 2 Oxoglutaric Acid, 2 Ketoglutaric Acid, hydron;2-oxopentanedioate, 2-ketoglutaric acid, Oxoglutarate, alpha-Oxoglutaric acid, alpha Ketoglutarate, Oxoglurate, Pentanedioic acid, oxo-, 2-ketoglutarate, alpha-Ketoglutaric acid, 2-oxo-pentanedioic acid, alpha-keto-Glutaric acid, alpha-Oxoglutaric acid, Glutaric acid, alpha-keto-, 2-Oxo-Glutaric Acid, 2-oxopentanedionate, 2-Ketoglutaric acid, AKG, alpha-Oxopentanedioic acid, alpha-Ketoglutaric acid, alpha-Ketoglutaricum acidum, alpha-oxo-glutaric acid, alpha-ketoglutarate, keto glutaric acid, 2-oxoglutaric-acid, G1utaric Acid;utaric acid;a,-Propanedicarboxylicacid;glutaric;Glutarsaure;1,3-PROPANEDICARBOXYLIC ACID;1,5-PENTADIOIC ACID;1,5-PENTANEDIOIC ACID
Pentanedioic acid (glutaric acid) is a dicarboxylic acid with carboxylic acid functional groups at either end of the molecular chain.
The terminal carboxylic acid groups can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.
Pentanedioic acid (glutaric acid) is the organic compound with the formula C3H6(COOH)2.
Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50% (w/w).
The Pentanedioic acid (glutaric acid) formula, also known as Pentanedioic acid formula or n-Pyrotartaric acid formula is discussed in this article.
Pentanedioic acid (glutaric acid) is an alpha,omega-dicarboxylic acid which has simple 5 carbon linear dicarboxylic acid (HO2C−R−CO2H).
The molecular or chemical formula of Glutaric acid is C5H8O4.
Chemically, glutaric acid contains two carboxyl groups (–COOH) separated by a three-carbon chain.
This structure allows it to participate in condensation and polymerization reactions.
Pentanedioic acid (glutaric acid) exhibits typical acidic behavior of dicarboxylic acids.
Physically, it appears as a white crystalline solid.
It is soluble in water and polar solvents.
Pentanedioic acid (glutaric acid) has a slightly acidic taste and odor.
Glutaric acid exhibits moderate acidity, with two dissociation steps (pKa₁ ≈ 4.3, pKa₂ ≈ 5.4).
It can form salts and esters.
This makes it useful in synthesis.
Pentanedioic acid (glutaric acid) is chemically reactive, especially in esterification and polymer formation reactions.
Pentanedioic acid (glutaric acid) can react with alcohols, amines, and other functional groups.
This supports its industrial use.
It is stable under normal conditions, but may decompose at high temperatures.
Proper storage ensures stability.
Pentanedioic acid (glutaric acid) should be kept in a dry environment.
Glutaric acid is used in chemical manufacturing and materials science as a building block.
It contributes to polymer and resin production.
This highlights its industrial importance.
Pentanedioic acid (glutaric acid) is best described as a versatile dicarboxylic acid used in synthesis, polymer production, and specialty chemical applications, valued for its reactivity and functionality.
Pentanedioic acid (glutaric acid) exhibits bifunctional reactivity due to its two carboxyl groups.
This allows it to react at both ends of the molecule.
Pentanedioic acid (glutaric acid) is useful in forming linear or crosslinked structures.
Pentanedioic acid (glutaric acid) can form hydrogen-bonded networks in solid and solution states.
These interactions influence melting point and solubility.
They contribute to its crystalline structure.
Pentanedioic acid (glutaric acid) shows moderate melting point (~95–98 °C) compared to shorter dicarboxylic acids.
Pentanedioic acid (glutaric acid)s chain length reduces intermolecular packing efficiency.
This affects thermal behavior.
Pentanedioic acid (glutaric acid) can act as a buffering agent in certain pH ranges, due to its two dissociation steps.
It helps maintain pH stability in solution.
This is useful in chemical systems.
The molecule is capable of forming salts (glutarates) with metals and bases.
These salts can have different solubility and reactivity.
This expands its application range.
Melting point: 95–98 °C (lit.)
Boiling point: 200 °C / 20 mmHg (lit.)
Density: 1.429 g/cm³
vapor pressure: 0.022 hPa (18.5 °C)
refractive index: nD106 1.41878
Flash point: 200 °C / 20 mmHg
storage temp.: Store below +30°C
solubility: water: soluble 5 mg/mL, clear to slightly hazy, colorless to faintly yellow
pKa: 4.31 (at 25℃)
form: Crystalline Powder
color: Orange
pH: 3.7 (1 mM solution); 3.17 (10 mM solution); 2.66 (100 mM solution)
Water Solubility: 430 g/L (20 ºC)
Merck: 14,4473
BRN: 1209725
Stability: Stable. Incompatible with bases, oxidizing agents, reducing agents
Cosmetics Ingredients Functions: BUFFERING
Cosmetic Ingredient Review (CIR): Glutaric acid (110-94-1)
InChI: 1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)
InChIKey: JFCQEDHGNNZCLN-UHFFFAOYSA-N
SMILES: OC(=O)CCCC(O)=O
LogP: -0.26 at 25℃
Pentanedioic acid (glutaric acid) is an alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.
Pentanedioic acid (glutaric acid) has a role as a human metabolite and a Daphnia magna metabolite.
It is an alpha,omega-dicarboxylic acid and a dicarboxylic fatty acid.
Pentanedioic acid (glutaric acid) is a conjugate acid of a glutarate(1-) and a glutarate.
Pentanedioic acid (glutaric acid) is naturally produced in the body during the metabolism of some amino acids, including lysine and tryptophan.
Pentanedioic acid (glutaric acid) can also arise by chain extension of α-ketoglutarate to α-ketoadipate.
Defects in this metabolic pathway can lead to a disorder called glutaric aciduria, where toxic byproducts build up and can cause severe encephalopathy.
Pentanedioic acid (glutaric acid) can be prepared by the ring-opening of butyrolactone with potassium cyanide to give the potassium salt of the carboxylate-nitrile that is hydrolyzed to the diacid.
Alternatively hydrolysis, followed by oxidation of dihydropyran gives glutaric acid.
Pentanedioic acid (glutaric acid) can also be prepared from reacting 1,3-dibromopropane with sodium or potassium cyanide to obtain the dinitrile, followed by hydrolysis.
Using periodate, it is obtained from oxidation of 1,3-cyclohexanedione, which proceeds with decarboxylation.
Pentanedioic acid (glutaric acid) is a straight-chain (aliphatic) dicarboxylic acid with five carbon atoms.
Its linear structure allows flexibility in molecular interactions.
This influences its reactivity and physical properties.
The molecule can undergo esterification reactions with alcohols to form diesters.
These esters are often used as plasticizers and intermediates.
This expands its industrial applications.
Pentanedioic acid (glutaric acid) can participate in polymerization and polycondensation reactions, forming polyesters and polyamides.
Pentanedioic acid (glutaric acid) reacts with diols or diamines.
This is important in materials science.
The compound exhibits good solubility in water due to its two carboxyl groups.
Pentanedioic acid (glutaric acid) can form hydrogen bonds with water molecules.
This enhances its reactivity in aqueous systems.
Pentanedioic acid (glutaric acid) can form cyclic anhydrides under certain conditions, especially upon heating.
This increases its reactivity in synthesis.
It enables additional chemical pathways.
Glutaric acid acts as a chelating or coordinating ligand with metal ions.
Pentanedioic acid (glutaric acid) can form complexes in solution.
This is relevant in analytical and coordination chemistry.
The compound shows intermediate chain length between short and long dicarboxylic acids, giving it balanced solubility and reactivity.
Pentanedioic acid (glutaric acid) is more flexible than shorter acids like oxalic acid.
This affects its applications.
Pentanedioic acid (glutaric acid) is also known as a metabolic intermediate in biological systems, particularly in amino acid degradation pathways.
Abnormal accumulation is linked to metabolic disorders (e.g., glutaric aciduria).
This highlights its biological relevance.
Pentanedioic acid (glutaric acid) is a flexible, water-soluble dicarboxylic acid with strong reactivity in esterification, polymerization, and coordination chemistry, making it valuable in both industrial and biochemical contexts.
Pentanedioic acid (glutaric acid) participates in decarboxylation and thermal reactions under strong conditions.
These reactions can produce smaller molecules.
This is relevant in advanced chemical processing.
It can influence plasticization and flexibility in polymer systems when used as an intermediate or additive.
Pentanedioic acid (glutaric acid) helps modify material properties.
This is important in polymer design.
The compound is often used in controlled synthesis pathways, where its chain length and reactivity provide predictable outcomes.
It enables design of specific molecular architectures.
This supports fine chemical production.
Pentanedioic acid (glutaric acid) is a bifunctional, moderately acidic, and structurally flexible molecule with diverse reactivity, making it highly useful in synthesis, materials science, and biochemical systems.
Uses:
Pentanedioic acid (glutaric acid) is used as the raw material for organic synthesis, pharmaceutical intermediate and synthetic resin.
Pentanedioic acid (glutaric acid) serves as a precursor in the production of polyester polyols, polyamides, ester plasticizers and corrosion inhibitors.
It is useful to decrease polymer elasticity and in the synthesis surfactants and metal finishing compounds.
Pentanedioic acid (glutaric acid) acts as an intermediate during the catabolism of lysine in mammals.
Pentanedioic acid (glutaric acid) is widely used as a chemical intermediate in polymer production, particularly in the synthesis of polyesters and polyamides.
It reacts with diols or diamines to form polymer chains.
This supports materials engineering.
In plasticizer production, glutaric acid is converted into esters (glutarates).
These esters improve flexibility and softness of plastics.
This enhances material performance.
Glutaric acid is used in pharmaceutical synthesis as a building block.
Pentanedioic acid (glutaric acid) helps produce active pharmaceutical ingredients and intermediates.
In coatings and resins, it contributes to formulation of specialty polymers.
Pentanedioic acid (glutaric acid) improves adhesion and chemical resistance.
This enhances coating durability.
Pentanedioic acid (glutaric acid) is applied in adhesives and sealants as a reactive intermediate.
Pentanedioic acid (glutaric acid) helps form strong polymer networks.
This improves bonding performance.
Pentanedioic acid (glutaric acid) is used in corrosion inhibitors and metal treatment formulations.
Pentanedioic acid (glutaric acid) can interact with metal surfaces.
This helps protect against degradation.
In laboratory and analytical chemistry, it is used as a reagent and standard.
Pentanedioic acid (glutaric acid) participates in synthesis and testing procedures.
This supports research work.
Pentanedioic acid (glutaric acid) is applied in biochemical and medical research as a reference compound.
It is used in studies related to metabolic pathways.
This aids scientific understanding.
Pentanedioic acid (glutaric acid) is also used in specialty chemical manufacturing, including synthesis of fine chemicals and intermediates.
It provides controlled reactivity.
Pentanedioic acid (glutaric acid) is used wherever bifunctional reactivity, polymer formation, and chemical synthesis are required across polymers, pharmaceuticals, coatings, and research applications.
Pentanedioic acid (glutaric acid), a common plasticizer and precursor to polyesters is manufactured by hydrogenation of glutaric acid and its derivatives.
Pentanedioic acid (glutaric acid) itself has been used in the production of polymers such as polyester polyols, polyamides. The odd number of carbon atoms (i.e. 5) is useful in decreasing polymer elasticity.
Pyrogallol can be produced from glutaric diester.
Pentanedioic acid (glutaric acid) is used in the production of biodegradable polymers and specialty plastics.
Its structure allows formation of environmentally friendly materials.
This supports sustainable material development.
In polyurethane and polyester resins, it acts as a chain extender or intermediate.
Pentanedioic acid (glutaric acid) helps tailor flexibility and mechanical properties.
This improves material performance.
Pentanedioic acid (glutaric acid) is applied in ink and coating additives to modify drying and adhesion properties.
It enhances film formation.
This improves coating quality.
Pentanedioic acid (glutaric acid) is used in flavor and fragrance chemistry as a precursor for ester derivatives.
These esters can contribute to aroma profiles.
This supports specialty chemical production.
In electrochemical and battery research, glutaric acid and its derivatives are studied as functional additives.
They can influence electrolyte behavior.
This supports advanced energy research.
Pentanedioic acid (glutaric acid) is applied in buffer systems and pH control formulations.
Its dual acidity allows controlled buffering.
This is useful in chemical processes.
Pentanedioic acid (glutaric acid) is used in textile finishing and processing chemicals.
Pentanedioic acid (glutaric acid) can modify fiber properties and interactions.
This improves treatment effectiveness.
In metal chelation and cleaning systems, it helps bind metal ions.
Pentanedioic acid (glutaric acid) supports removal of contaminants.
This enhances cleaning efficiency.
Pentanedioic acid (glutaric acid) is also used in fine chemical synthesis for producing intermediates in dyes, coatings, and specialty materials.
Pentanedioic acid (glutaric acid) provides predictable reactivity.
Pentanedioic acid (glutaric acid) is used wherever polymer modification, intermediate synthesis, buffering, and specialty chemical production are required across industrial, research, and advanced material applications.
Safety Profile:
Pentanedioic acid (glutaric acid) may cause irritation to the skin and eyes.[7] Acute hazards include the fact that this compound may be harmful by ingestion, inhalation or skin absorption.
Pentanedioic acid (glutaric acid) presents low to moderate hazards, mainly due to its acidic nature and potential for irritation.
It is less hazardous than strong mineral acids but still requires careful handling.
Skin contact may cause mild to moderate irritation, especially with prolonged exposure.
Symptoms can include redness or dryness.
Protective gloves are recommended.
Eye contact can cause irritation or discomfort.
Symptoms include redness, tearing, and stinging sensation.
Eyes should be rinsed thoroughly with water if exposure occurs.
Inhalation of dust may cause respiratory irritation.
Fine particles can irritate the nose, throat, and lungs.
Adequate ventilation and dust control are important.
Pentanedioic acid (glutaric acid) ingestion may cause gastrointestinal irritation.
Symptoms can include nausea or stomach discomfort.
Large amounts should be avoided and medical advice sought if necessary.
