Pentanedioic acid (glutaric acid) is primarily utilized in the production of glutaric anhydride, synthetic rubber, and synthetic resins.
Pentanedioic acid (glutaric acid) also serves as a polymerization initiator in various chemical processes.
Pentanedioic acid (glutaric acid) is widely used in industrial chemistry and synthesis.
CAS Number: 110-94-1
EC Number: 203-817-2
Molecular Formula: C5H8O4
Molecular Weight: 132.11 g/mol
SYNONYMS:
Glutaric acid, Pentanedioic acid, 1,3-Propanedicarboxylic acid, 1,5-Pentanedioic acid, Propane-1,3-dicarboxylic acid, Pentanedioic acid, Glutaric acid, Propane-1,3-dicarboxylic acid, 1,3-Propanedicarboxylic acid, Pentanedioic acid, n-Pyrotartaric acid, 1,5-Pentanedioic acid, GLUTARIC ACID, Pentanedioic acid, 110-94-1, 1,5-Pentanedioic acid, glutarate, 1,3-Propanedicarboxylic acid, Pentandioic acid, n-Pyrotartaric acid, DTXSID2021654, CHEBI:17859, H849F7N00B, NSC-9238, DTXCID401654, RefChem:5863, CHEBI:24329, 203-817-2, hydron, pentanedioate, Pentanedioate, propane-1,3-dicarboxylic acid, MFCD00004410, Abacavir related, NSC9238, CAS-110-94-1, HSDB 5542, NSC 9238, EINECS 203-817-2, BRN 1209725, Glutarsaeure, Pentandioate, UNII-H849F7N00B, AI3-24247, 1czc, 1,5-Pentanedioate, Glutaric acid, 99%, 4lh3, 1,3-Propanedicarboxylate, Glutaric acid (Standard), WLN: QV3VQ, bmse000406, Adipic Acid EP Impurity A, GLUTARIC ACID [MI], SCHEMBL7414, GLUTARIC ACID [HSDB], 4-02-00-01934 (Beilstein Handbook Reference), SCHEMBL490683, SCHEMBL596335, Pentanedioic acid Glutaric acid, orb1302560, SCHEMBL1573678, CHEMBL1162495, HMS5086G14, BB_SC-13044, HY-W008820R, Tox21_202448, Tox21_302871, BDBM50485550, EBC-04275, MSK2566-100M, s3152, SBB060277, AKOS000118800, MSK2566-1000M, 1,3-PENTANEDIOIC ACID (RIFM), CS-W009536, DB03553, FG02567, HY-W008820, NCGC00249226-01, NCGC00256456-01, NCGC00259997-01, AS-13132, BP-21143, SY029948, ADIPIC ACID IMPURITY A [EP IMPURITY], G0069, G0245, NS00003673, ST51046496, EN300-17991, Glutaric acid Solution in Methanol, 100ug/mL, C00489, D70283, Glutaric acid Solution in Methanol, 1000ug/mL, F790971, Q409622, Glutaric Acid (ca. 50% in Water, ca. 4.3mol/L), Z57127454, 78FA13BF-E0C0-4EFC-948C-534CF45044E3, F2191-0242, Glutaric acid, certified reference material, TraceCERT(R), InChI=1/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9, glutaricacid, hydrogen glutarate, pentane dioic acid, 1,5-pentane dioic acid, pentanedioc acid, pentanedioic acid, 1,5-pentanedioic acid, pentanedioic acid glutaric acid, 1,3-propane dicarboxylic acid, propane-1,3-dicarboxylic acid, 1,3-propanedicarboxylate, 1,3-propanedicarboxylic acid, N-pyrotartaric acid, Glutaric acid, 1,3-Propanedicarboxylic acid, 1,5-Pentanedioic acid, Pentandioic acid, G1utaric Acid, utaric acid, a,-Propanedicarboxylicacid, glutaric, Glutarsaure, 1,3-PROPANEDICARBOXYLIC ACID, 1,5-PENTADIOIC ACID, 1,5-PENTANEDIOIC ACID, 1,3-Propanedicarboxylate, Generator, 1,3-Propanedicarboxylic acid, ChEBI, 1,5-Pentanedioate, Generator, 1,5-Pentanedioic acid, ChEBI, Glutarate, Generator, Glutaric acid, manual, Glutarsaeure, ChEBI, Pentandioate, HMDB, Pentandioic acid, HMDB, Pentanedioate, GLUTARIC ACID, Pentanedioic acid, 110-94-1, 1,5-Pentanedioic acid, glutarate, 1,3-Propanedicarboxylic acid, Pentandioic acid, n-Pyrotartaric acid, propane-1,3-dicarboxylic acid, UNII-H849F7N00B, CHEBI:17859, MFCD00004410, Carboxylic acids, C6-18 and C5-15-di-, NSC9238, H849F7N00B, DSSTox_CID_1654, DSSTox_RID_76266, DSSTox_GSID_21654, CAS-110-94-1, HSDB 5542, NSC 9238, EINECS 203-817-2, BRN 1209725, Glutarsaeure, Pentandioate, AI3-24247, 1czc, 1,5-Pentanedioate, Glutaric acid, 99%, 4lh3, 1,3-Propanedicarboxylate, WLN: QV3VQ, (C4-C6) Dibasic acids, pentanedioate, Glutaric acid, bmse000406, Glutaric Acid and Anhydride, SCHEMBL7414, 4-02-00-01934, Pentanedioic acid Glutaric acid, Carboxylic acids, di-, C4-6, CHEMBL1162495, DTXSID2021654, ZINC388706, NSC-9238, Tox21_202448, Tox21_302871, BDBM50485550, s3152, AKOS000118800, CS-W009536, DB03553, HY-W008820, LS41863, MCULE-4286022994, NCGC00249226-01, NCGC00256456-01, NCGC00259997-01, 68937-69-9, AS-13132, BP-21143, H402, SY029948, FT-0605446, G0069, G0245, C00489, D70283, A802271, Q409622, Glutaric Acid (ca. 50% in Water, ca. 4.3mol/L), J-011915, Q-201163, Z57127454, 78FA13BF-E0C0-4EFC-948C-534CF45044E3, F2191-0242, Glutaric acid, certified reference material, TraceCERT(R), Glutaric acid, 1,3-Propanedicarboxylate, 1,5-Pentanedioate, 1,5-Pentanedioic acid, 110-94-1, 1209725, 203-817-2, Acide glutarique, Glutarsäure, hydrogen glutarate, MFCD00004410, n-Pyrotartaric acid, Pentanedioic acid, 1,3-PROPANEDICARBOXYLIC ACID, 111-16-0, 154184-99-3, 19136-99-3, 203-817-2MFCD00004410, 271-678-5, 273-081-5, 4-02-00-01934, 43087-19-0, 68603-87-2, 68937-69-9, 8065-59-6, Glutaric acid (Pentanedioic acid), glutaric acid, reagent, Gua, hydron, Pentandioate, Pentandioic acid, pentanedioate, Pentanedioic-2,2,4,4-d4 Acid, Pentanedioic-3,3-d2 Acid, Pentanedioic-d6 Acid, Propane-1,3-dicarboxylic acid, Propane-1,3-dicarboxylic acid|Pentanedioic acid, Glutaric acid, WLN: QV3VQ
Pentanedioic acid (glutaric acid) is a five-carbon linear alpha, omega-dicarboxylic acid with the chemical formula C₅H₈O₄.
Pentanedioic acid (glutaric acid) is naturally formed in mammals as an intermediate product during the catabolism of certain amino acids such as lysine and tryptophan.
Pentanedioic acid (glutaric acid) can be synthesized by various methods such as oxidation of cyclopentane, cyclopentanol and cyclopentanone.
Pentanedioic acid (glutaric acid) is a white crystalline dicarboxylic acid, also known as pentanedioic acid, with a melting point of 95–98°C.
Pentanedioic acid (glutaric acid) is a naturally occurring metabolite in amino acid catabolism, soluble in water, and used heavily in industry for producing polymers like polyester polyols and nylon.
Pentanedioic acid (glutaric acid) is a raw material for the production of glutaric anhydride and is used as an initiator in the polymerization of synthetic resins and synthetic rubbers.
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 Pentanedioic acid (glutaric acid) is over 50% (w/w).
Pentanedioic acid (glutaric acid) is a simple five-carbon linear dicarboxylic acid.
The accumulation of Pentanedioic acid (glutaric acid) ranging from slightly or intermittently elevated urinary Pentanedioic acid (glutaric acid) to gross organic aciduria occurs in Pentanedioic acid (glutaric acid)uria.
Pentanedioic acid (glutaric acid)uria type 1 is an autosomal-recessive disorder resulting from a deficiency of mitochondrial glutaryl-CoA dehydrogenase (EC 1.3.99.7, GCDH) which is involved in the metabolism of lysine, hydroxylysine, and tryptophan.
Pentanedioic acid (glutaric acid)uria type I lead to nonspecific developmental delay, hypotonia, and macrocephaly with cerebral atrophy of prenatal onset.
Treatment is mainly based on restriction of lysine intake, supplementation of carnitine, and an intensification of therapy during intercurrent illnesses.
The major principle of dietary treatment is to reduce the production of Pentanedioic acid (glutaric acid) and 3-hydroxyPentanedioic acid (glutaric acid) by restriction of natural protein in general and of lysine in particular.
Pentanedioic acid (glutaric acid) is a linear aliphatic dicarboxylic acid containing two carboxyl groups (–COOH) separated by three methylene groups.
Pentanedioic acid (glutaric acid) is an organic compound widely used as an intermediate in chemical synthesis, pharmaceuticals, and polymer chemistry.
In biological systems, Pentanedioic acid (glutaric acid) can occur as an intermediate during the metabolism of amino acids such as lysine.
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 Pentanedioic acid (glutaric acid) is over 50% (w/w).
1,5-Pentanediol, a common plasticizer and precursor to polyesters is manufactured by hydrogenation of Pentanedioic acid (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) appears as colorless crystals or white solid.
Pentanedioic acid (glutaric acid) is an alpha,-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.
Pentanedioic acid (glutaric acid) is a dicarboxylic fatty acid and an alpha,omega-dicarboxylic acid.
Pentanedioic acid (glutaric acid) is a conjugate acid of a glutarate and a glutarate(1-).
Pentanedioic acid (glutaric acid) is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Pentanedioic acid (glutaric acid) has been reported in Glycine max, Drosophila melanogaster, and other organisms with data available.
Pentanedioic acid (glutaric acid) is a simple five-carbon linear dicarboxylic acid.
The accumulation of Pentanedioic acid (glutaric acid) ranging from slightly or intermittently elevated urinary Pentanedioic acid (glutaric acid) to gross organic aciduria occurs in Pentanedioic acid (glutaric acid)uria.
Pentanedioic acid (glutaric acid)uria type 1 is an autosomal-recessive disorder resulting from a deficiency of mitochondrial glutaryl-CoA dehydrogenase (EC 1.3.99.7, GCDH) which is involved in the metabolism of lysine, hydroxylysine, and tryptophan.
Pentanedioic acid (glutaric acid)uria type I lead to nonspecific developmental delay, hypotonia, and macrocephaly with cerebral atrophy of prenatal onset.
Treatment is mainly based on restriction of lysine intake, supplementation of carnitine, and an intensification of therapy during intercurrent illnesses.
The major principle of dietary treatment is to reduce the production of Pentanedioic acid (glutaric acid) and 3-hydroxyPentanedioic acid (glutaric acid) by restriction of natural protein in general and of lysine in particular.
Pentanedioic acid (glutaric acid), also known as 1,5-pentanedioate or pentanedioic acid, belongs to the class of organic compounds known as dicarboxylic acids and derivatives.
These are organic compounds containing exactly two carboxylic acid groups.
Pentanedioic acid (glutaric acid) exists in all living organisms, ranging from bacteria to humans.
Pentanedioic acid (glutaric acid) is an odorless tasting compound.
Pentanedioic acid (glutaric acid) has been detected, but not quantified in, several different foods, such as eddoes (Colocasia antiquorum), pitangas (Eugenia uniflora), narrowleaf cattails (Typha angustifolia), chicory leaves (Cichorium intybus var. foliosum), and wax apples (Eugenia javanica).
This could make Pentanedioic acid (glutaric acid) a potential biomarker for the consumption of these foods.
Pentanedioic acid (glutaric acid) belongs to the class of organic compounds known as dicarboxylic acids and derivatives.
These are organic compounds containing exactly two carboxylic acid groups.
Pentanedioic acid (glutaric acid), also known as pentanedioic acid, is a dicarboxylic acid with the chemical formula C5H8O4.
Pentanedioic acid (glutaric acid) is characterized by its needle-like crystal appearance and remarkable water solubility, distinguishing it from shorter and longer chain dicarboxylic acids.
As a key organic intermediate, Pentanedioic acid (glutaric acid) plays a significant role in the chemical industry, particularly in the synthesis of various polymers and resins.
For businesses seeking reliable sourcing, understanding the applications and availability of Pentanedioic acid (glutaric acid) from a trusted manufacturer in China is paramount.
One of the primary uses of Pentanedioic acid (glutaric acid) is as a monomer in the production of polymers.
Pentanedioic acid (glutaric acid)'s unique structure, featuring an odd number of carbon atoms, allows for the creation of polymers with specific elastic properties.
For instance, Pentanedioic acid (glutaric acid) is utilized in the synthesis of polyester polyols and polyamides.
These polymers find applications in diverse fields ranging from textiles and engineering plastics to coatings and adhesives.
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Beyond its role in polymer chains, Pentanedioic acid (glutaric acid) also functions as an initiator in the polymerization of resins and rubber.
This function is critical for controlling the reaction kinetics and ensuring the desired molecular weight and properties of the final product.
The ability to source high-quality Pentanedioic acid (glutaric acid) from a consistent manufacturer ensures the predictability and efficiency of these polymerization processes.
The chemical industry relies heavily on versatile intermediates like Pentanedioic acid (glutaric acid) for a myriad of organic synthesis applications.
Its reactivity and functional groups make Pentanedioic acid (glutaric acid) an ideal building block for creating more complex molecules.
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The Pentanedioic acid (glutaric acid) formula, also known as Pentanedioic acid formula or n-Pyrotartaric acid formula.
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 Pentanedioic acid (glutaric acid) is C5H8O4.
When Pentanedioic acid (glutaric acid) is present in a high amount it acts as a metabotoxin and as an acidogen.
Pentanedioic acid (glutaric acid) can be synthesized by the following process.
The ring-opening of butyrolactone (C4H6O2) with potassium cyanide (KCN) to produce potassium carboxylate-nitrile.
Pentanedioic acid (glutaric acid) is hydrolyzed further to diacid.
Oxidizing dihydropyran will produce Pentanedioic acid (glutaric acid).
Pentanedioic acid (glutaric acid) can also be synthesized by treating 1,3-dibromopropane with potassium or sodium cyanide to produce dinitrile.
Further, it is hydrolysed to obtain Pentanedioic acid (glutaric acid).
n-Pyrotartaric acid is naturally produced by the body during the process of metabolism of certain amino acids, which include tryptophan and including lysine.
Any defect in the pathway can cause disorder such as Pentanedioic acid (glutaric acid)uria which results in severe encephalopathy.
Pentanedioic acid (glutaric acid) is a naturally occurring dicarboxylic acid commonly found in the human body as a byproduct of amino acid metabolism.
Pentanedioic acid (glutaric acid) plays a role in biochemical processes and is associated with certain metabolic disorders, such as Pentanedioic acid (glutaric acid)uria, where the body accumulates harmful levels of Pentanedioic acid (glutaric acid).
Pentanedioic acid (glutaric acid) appears as colorless crystals or white solid.
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.
Pentanedioic acid (glutaric acid) 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 a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Pentanedioic acid (glutaric acid), also known as pentanedioic acid, is an organic compound with the molecular formula C5H8O4.
Pentanedioic acid (glutaric acid) is classified as a dicarboxylic acid, featuring two carboxyl functional groups (-COOH) at each end of a five-carbon linear chain.
This structure grants Pentanedioic acid (glutaric acid) unique properties, including high water solubility (over 50% w/w) compared to related dicarboxylic acids like adipic and succinic acids, which have lower solubility at room temperature.
USES and APPLICATIONS of PENTANEDIOIC ACID (GLUTARIC ACID):
Pentanedioic acid (glutaric acid) has diverse applications across various industries.
Polymer Production: Pentanedioic acid (glutaric acid) is used in manufacturing polyamides and polyurethanes due to its ability to modify polymer properties.
Plasticizers: Hydrogenation derivatives serve as plasticizers in consumer goods.
Pharmaceuticals: Pentanedioic acid (glutaric acid)'s derivatives are explored for potential therapeutic applications due to their biological activity.
Food Industry: Pentanedioic acid (glutaric acid) is used as an acidity regulator and flavoring agent.
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.
1.5-Pentanediol, a common plasticizer and precursor to polyesters is manufactured by hydrogenation of Pentanedioic acid (glutaric acid) and its derivatives.
Pentanedioic acid (glutaric acid) is primarily utilized in the production of glutaric anhydride, synthetic rubber, and synthetic resins.
Pentanedioic acid (glutaric acid) also serves as a polymerization initiator in various chemical processes.
Pentanedioic acid (glutaric acid) is widely used in industrial chemistry and synthesis.
Hydrogenation of Pentanedioic acid (glutaric acid) and its derivatives produces a plasticizers.
Used to produce many polymers such as polyesters, polyamides.
-Chemical Industry uses of Pentanedioic acid (glutaric acid):
Intermediate in organic synthesis.
Raw material for polyesters and polyamides.
Pentanedioic acid (glutaric acid) is used in the preparation of plasticizers.
-Pharmaceutical Industry uses of Pentanedioic acid (glutaric acid):
Pentanedioic acid (glutaric acid) is used as a pharmaceutical intermediate.
Pentanedioic acid (glutaric acid) is applied in synthesis of active pharmaceutical ingredients (APIs).
-Polymer and Material Science uses of Pentanedioic acid (glutaric acid):
Production of specialty polymers and resins.
Pentanedioic acid (glutaric acid) is used for biodegradable materials research.
-Laboratory Applications of Pentanedioic acid (glutaric acid):
Analytical reagent in chemical research.
Intermediate in synthesis of fine chemicals.
-Food & Healthcare Ingredients use of Pentanedioic acid (glutaric acid):
*Flavoring Agent:
Pentanedioic acid (glutaric acid) can be used as a flavoring agent in various food and beverage products.
Pentanedioic acid (glutaric acid) provides a tangy taste and can be used in flavor formulations for candies, beverages, and dairy products.
*Preservative:
Pentanedioic acid (glutaric acid)'s antimicrobial properties help in preserving food items by inhibiting the growth of bacteria and fungi, thereby extending the shelf life of packaged foods.
-Pharmaceuticals uses of Pentanedioic acid (glutaric acid):
*Intermediate in Drug Synthesis:
Pentanedioic acid (glutaric acid) is used as a chemical intermediate in the synthesis of various pharmaceuticals.
Pentanedioic acid (glutaric acid) serves as a precursor to drugs and other biologically active compounds.
*Excipient:
Pentanedioic acid (glutaric acid) is used as an excipient to adjust pH and enhance the stability and solubility of active ingredients in pharmaceutical formulations.
*Controlled Release Formulations:
Pentanedioic acid (glutaric acid) derivatives are utilized in controlled-release formulations to modulate the release rate of the active pharmaceutical ingredient.
-Personal Care uses of Pentanedioic acid (glutaric acid):
*pH Adjuster:
Pentanedioic acid (glutaric acid) is used in skincare and cosmetic formulations to adjust the pH levels, enhancing the stability and effectiveness of other ingredients in creams, lotions, and serums.
*Humectant:
Pentanedioic acid (glutaric acid) acts as a humectant in personal care products, helping to retain moisture and providing hydration to the skin.
-Chemical Synthesis uses of Pentanedioic acid (glutaric acid):
*Polyester and Alkyd Resin Production:
Pentanedioic acid (glutaric acid) is a key intermediate in the production of polyester and alkyd resins, which are used in coatings, adhesives, and plastics industries.
*Plasticizer:
Pentanedioic acid (glutaric acid) is used as a plasticizer in the production of flexible plastics, improving their durability, flexibility, and handling properties.
*Corrosion Inhibitor:
Pentanedioic acid (glutaric acid) is utilized in various industrial processes as a corrosion inhibitor, especially in metal cleaning and maintenance.
-Fabric Solutions use of Pentanedioic acid (glutaric acid):
*Dyeing & Finishing Agent:
In the textile industry, Pentanedioic acid (glutaric acid) is used as a finishing agent to improve the dye uptake of fabrics and to enhance the brightness and durability of colors.
*pH Modifier:
Pentanedioic acid (glutaric acid) is used as a pH modifier in textile processing, helping to maintain the right acidity levels during various stages of fabric treatment.
-Scientific Research Applications of Pentanedioic acid (glutaric acid):
*Production of Bio-based Chemicals
Traditionally, Pentanedioic acid (glutaric acid) has been produced through petroleum-based methods.
However, scientific research is exploring alternative bio-based production methods.
These methods utilize microorganisms like Corynebacterium glutamicum to convert renewable resources like lysine into Pentanedioic acid (glutaric acid).
This approach is described in a research article published in the National Institutes of Health's National Center for Biotechnology Information.
Bio-based production of Pentanedioic acid (glutaric acid) is considered more sustainable compared to traditional methods.
ALTERNATIVE PARENTS of PENTANEDIOIC ACID (GLUTARIC ACID):
*Fatty acids and conjugates
*Carboxylic acids
*Organic oxides
*Hydrocarbon derivatives
*Carbonyl compounds
SUBSTITUENTS of PENTANEDIOIC ACID (GLUTARIC ACID):
*Fatty acid
*Dicarboxylic acid or derivatives
*Carboxylic acid
*Organic oxygen compound
*Organic oxide
*Hydrocarbon derivative
*Organooxygen compound
*Carbonyl group
*Aliphatic acyclic compound
BENEFITS AND INDUSTRIAL IMPORTANCE of PENTANEDIOIC ACID (GLUTARIC ACID):
Important building block in organic synthesis.
Good water solubility, making it useful for aqueous reactions.
Stable organic acid with predictable reactivity.
Versatile precursor for esters and polymers.
Valuable chemical intermediate in pharmaceuticals and materials science.
MECHANISM OF ACTION of PENTANEDIOIC ACID (GLUTARIC ACID):
In biological systems, Pentanedioic acid (glutaric acid) is an intermediate metabolite produced during amino acid breakdown.
However, Pentanedioic acid (glutaric acid)'s specific mechanism of action beyond this role remains unclear.
In GA-I, a deficiency in the enzyme glutaryl-CoA dehydrogenase leads to the accumulation of Pentanedioic acid (glutaric acid) and other metabolites, causing neurological damage.
BIOLOGICAL ACTIVITY of PENTANEDIOIC ACID (GLUTARIC ACID):
Pentanedioic acid (glutaric acid) plays significant roles in biological systems, particularly in amino acid metabolism.
Pentanedioic acid (glutaric acid) is involved in the catabolism of lysine and tryptophan.
Deficiencies in the enzymes responsible for these metabolic pathways can lead to Pentanedioic acid (glutaric acid)uria, resulting in harmful accumulations that may cause severe encephalopathy and other neurological disorders.
In addition to its metabolic role, Pentanedioic acid (glutaric acid) exhibits antimicrobial properties and has been studied for its potential applications in pharmaceuticals.
STRUCTURAL AND MOLECULAR CHARACTERISTICS of PENTANEDIOIC ACID (GLUTARIC ACID):
Pentanedioic acid (glutaric acid) contains two terminal carboxyl groups.
Linear carbon chain with five carbon atoms.
Classified as a dicarboxylic acid homologous with adipic acid and succinic acid.
Pentanedioic acid (glutaric acid) forms hydrogen bonds in crystalline structures.
Pentanedioic acid (glutaric acid) can generate stable free radicals when exposed to radiation in crystals.
BIOCHEMISTRY of PENTANEDIOIC ACID (GLUTARIC ACID):
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 Pentanedioic acid (glutaric acid)uria, where toxic byproducts build up and can cause severe encephalopathy.
PRODUCTION of PENTANEDIOIC ACID (GLUTARIC ACID):
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 Pentanedioic acid (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, Pentanedioic acid (glutaric acid) is obtained from oxidation of 1,3-cyclohexanedione, which proceeds with decarboxylation.
CHEMICAL REACTIONS of PENTANEDIOIC ACID (GLUTARIC ACID):
Typical of carboxylic acids.
It can undergo:
*Neutralization:
Reacting with bases to form salts and water.
*Esterification:
Reacting with alcohols to form esters.
*Reduction:
Hydrogenation can convert Pentanedioic acid (glutaric acid) into 1,5-pentanediol, a common plasticizer.
*Decarboxylation:
Under certain conditions, it can lose carbon dioxide.
The synthesis of Pentanedioic acid (glutaric acid) can also be achieved through several pathways:
*Ring-opening of Butyrolactone:
Using potassium cyanide to produce a potassium salt that is hydrolyzed to form Pentanedioic acid (glutaric acid).
*Hydrolysis of Dinitrile:
From 1,3-dibromopropane reacting with sodium or potassium cyanide.
*Oxidation of Dihydropyran:
This method involves oxidizing dihydropyran to yield Pentanedioic acid (glutaric acid).
SYNTHESIS METHODS of PENTANEDIOIC ACID (GLUTARIC ACID):
The synthesis of Pentanedioic acid (glutaric acid) can be achieved through various methods:
*Chemical Synthesis:
Malonic Ester Synthesis:
Involves di-iodomethane reacting with diethyl malonate followed by treatment with a strong base.
Oxidation Reactions:
Such as the oxidation of 2-cyanocyclopentanone or condensation reactions involving acrylonitrile.
*Biotechnological Approaches:
Recent advances include metabolic engineering techniques to enhance microbial production of Pentanedioic acid (glutaric acid) from renewable resources.
For instance, engineered strains of Escherichia coli have been developed to produce Pentanedioic acid (glutaric acid) efficiently through optimized fermentation conditions.
PHYSICAL and CHEMICAL PROPERTIES of PENTANEDIOIC ACID (GLUTARIC ACID):
IUPAC Name: Pentanedioic acid
Common Name: Glutaric acid
CAS Number: 110-94-1
EC Number: 203-817-2
Molecular Formula: C5H8O4
Molecular Weight: 132.11 g/mol
Chemical Structure Formula: HOOC(CH2)3COOH
SMILES: OC(=O)CCCC(O)=O
InChIKey: JFCQEDHGNNZCLN-UHFFFAOYSA-N
Appearance: White crystalline solid or powder
Odor: Odorless or faint odor
Density: ~1.42–1.43 g/cm³
Melting Point: 95–99 °C
Boiling Point: ~302–304 °C (decomposes)
Flash Point: ~151–190 °C
Water Solubility: Very soluble (~430 g/L at 20 °C)
Vapor Pressure: ~0.022 hPa at 18.5 °C
Refractive Index: ~1.477
Physical Form: Crystalline powder or monoclinic crystals
Chemical Class: Aliphatic dicarboxylic acid
Acidity (pKa): pKa1 ≈ 4.34, pKa2 ≈ 5.41
LogP: −1.04
Stability: Stable under normal conditions
Reactivity: Reacts with bases to form salts (glutarates); can form esters with alcohols;
may react with oxidizing agents or reducing agents
Thermal Behavior: Decomposes at high temperature
Solubility: Soluble in water, ethanol, ether, benzene, chloroform
CAS Number: 110-94-1
ChEBI: CHEBI:17859
ChEMBL: ChEMBL1162495
ChemSpider: 723
DrugBank: DB03553
ECHA InfoCard: 100.003.471
EC Number: 203-817-2
Gmelin Reference: 26809
KEGG: C00489
PubChem CID: 743
UNII: H849F7N00B
Molecular Weight: 132.11 g/mol
XLogP3: -0.3
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 4
Exact Mass: 132.04225873 Da
Monoisotopic Mass: 132.04225873 Da
Topological Polar Surface Area: 74.6 Ų
Heavy Atom Count: 9
Formal Charge: 0
Complexity: 104
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
ECHA EINECS - REACH Pre-Reg: 203-817-2
FDA UNII: H849F7N00B
Nikkaji Web: J40.077G
Beilstein Number: 1209725
MDL: MFCD00004410
XlogP3: -0.30 (est)
Molecular Weight: 132.11556000
Formula: C5 H8 O4
Appearance: white to tan crystals (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 98.00 °C @ 760.00 mm Hg
Boiling Point: 303.00 °C @ 760.00 mm Hg
Boiling Point: 200.00 °C @ 20.00 mm Hg
Flash Point: 304.00 °F TCC (151.20 °C) (est)
logP (o/w): -0.290
Soluble in: alcohol; water, 1600000 mg/L @ 28 °C
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 mm
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 °C)
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 °C)
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 °C
CAS DataBase Reference: 110-94-1 (CAS DataBase Reference)
NIST Chemistry Reference: Pentanedioic acid (110-94-1)
EPA Substance Registry System: Pentanedioic acid (110-94-1)
LogP: 0.046
pKa (Strongest Acidic): 3.76
Physiological Charge: -2
Hydrogen Acceptor Count: 4
Hydrogen Donor Count: 2
Polar Surface Area: 74.6 Ų
Rotatable Bond Count: 4
Refractivity: 28.14 m³•mol⁻¹
Polarizability: 12.17 ų
Number of Rings: 0
Bioavailability: Yes
Rule of Five: Yes
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: No
Chemical Formula: C5H8O4
IUPAC Name: pentanedioic acid
InChI Identifier: InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)
InChI Key: JFCQEDHGNNZCLN-UHFFFAOYSA-N
Isomeric SMILES: OC(=O)CCCC(O)=O
Average Molecular Weight: 132.1146
Monoisotopic Molecular Weight: 132.042258744
Linear Formula: HOOC(CH2)3COOH
CAS Number: 110-94-1
Molecular Weight: 132.11 g/mol
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24895125
EC Number: 203-817-2
Beilstein/REAXYS Number: 1209725
MDL Number: MFCD00004410
Assay: 99%
Product Name: Glutaric acid
SMILES: C(CC(=O)O)CC(=O)O
Solubility: greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)
Solubility in Water (g/L): @0°C: 429; @20°C: 639; @50°C: 957; @65°C: 1118;
Freely soluble in absolute alcohol, ether; soluble in benzene, chloroform;
slightly soluble in petroleum ether
Soluble in concentrated sulfuric acid: 1600 mg/mL
Solubility in water, g/100 mL at 20 °C: 63.9
Canonical SMILES: C(CC(=O)O)CC(=O)O
Physical State: solid
Color: white, off-white
Odor: No data available
Melting Point / Freezing Point: 95–98 °C (lit.)
Initial Boiling Point and Boiling Range: 200 °C at 27 hPa (lit.)
Flammability (solid, gas): No data available
Upper / Lower Flammability or Explosive Limits: No data available
Flash Point: Not applicable
Autoignition Temperature: No data available
Decomposition Temperature: No data available
pH: No data available
Viscosity, dynamic: No data available
Viscosity, kinematic: No data available
Water Solubility: 130 g/L at 23.9 °C
Partition Coefficient: n-octanol/water log Pow: -0.256;
Bioaccumulation is not expected
Vapor Pressure: <1 hPa at 121 °C
Density: 1.429 g/cm³ at 15 °C
Relative Density: No data available
Relative Vapour Density: No data available
Particle Characteristics: No data available
Explosive Properties: No data available
Oxidizing Properties: none
Other Safety Information: No data available
FIRST AID MEASURES of PENTANEDIOIC ACID (GLUTARIC ACID):
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of PENTANEDIOIC ACID (GLUTARIC ACID):
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of PENTANEDIOIC ACID (GLUTARIC ACID):
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of PENTANEDIOIC ACID (GLUTARIC ACID):
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of PENTANEDIOIC ACID (GLUTARIC ACID):
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of PENTANEDIOIC ACID (GLUTARIC ACID):
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available