PRODUCTS

PENTANEDIOIC ACID (GLUTARIC ACID)

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 an alpha, omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.

CAS Number: 110-94-1
EC Number: 203-817-2
IUPAC Name: Pentanedioic acid
Chemical Formula: C5H8O4

Other names: 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) 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.

Biochemistry
Pentanedioic acid (Glutaric acid) is naturally produced in the body during the metabolism of some amino acids, including lysine and tryptophan.
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
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, it is obtained from oxidation of 1,3-cyclohexanedione, which proceeds with decarboxylation.

Uses
Pentanedioic acid (Glutaric acid), 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) is a linear dicarboxylic acid.
Pentanedioic acid (Glutaric acid) has been prepared by oxidizing cyclopentane, cyclopentanol and cyclopentanone.
On exposure to X-rays, Pentanedioic acid (Glutaric acid) crystals generate two stable free radicals.
These free radicals have been investigated by electron nuclear double resonance (ENDOR) technique.
Presence of Pentanedioic acid (Glutaric acid) in urine and plasma is an indicator of type I Pentanedioic acid (Glutaric acid)uria (GA-I).

Pentanedioic acid (Glutaric acid) is formed as an intermediate during the catabolism of lysine in mammals.
Electron spin resonance spectra of radical (CO2H)CH2CH2CH(CO2H formed in Pentanedioic acid (Glutaric acid) crystal after γ-irradiation is reported to remains trapped in Pentanedioic acid (Glutaric acid).
Polymorphism of Glycine-Pentanedioic acid (Glutaric acid) co-crystals has been studied by single crystal X-ray diffraction and Raman spectroscopy.

Pentanedioic acid (Glutaric acid) is a simple five-carbon linear dicarboxylic acid.
Pentanedioic acid (Glutaric acid) is naturally produced in the body during the metabolism of some amino acids, including lysine and tryptophan.

Molar mass: 132.12 g/mol
Melting point: 95 to 98 °C
Boiling point: 200 °C
Molecular Weight: 132.11

XLogP3: -0.3
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 4

Exact Mass: 132.04225873
Monoisotopic Mass: 132.04225873
Topological Polar Surface Area: 74.6 Å²
Heavy Atom Count: 9

Complexity: 104
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Density: 1.429 g/cm3 (15 °C)
Melting Point: 97.5 - 98 °C

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 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) may cause irritation to the skin and eyes.
When present in sufficiently high levels, Pentanedioic acid (Glutaric acid) can act as an acidogen and a metabotoxin.

An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems.
A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels.

Chronically high levels of Pentanedioic acid (Glutaric acid) are associated with at least three inborn errors of metabolism, including Pentanedioic acid (Glutaric acid)uria type I, malonyl-CoA decarboxylase deficiency, and Pentanedioic acid (Glutaric acid)uria type III.
Pentanedioic acid (Glutaric acid)uria type I (Pentanedioic acid (Glutaric acid)emia type I, glutaryl-CoA dehydrogenase deficiency, GA1, or GAT1) is an inherited disorder in which the body is unable to completely break down the amino acids lysine, hydroxylysine, and tryptophan due to a deficiency of mitochondrial glutaryl-CoA dehydrogenase (EC 1.3.99.7, GCDH).

Excessive levels of their intermediate breakdown products (e.g. Pentanedioic acid (Glutaric acid), glutaryl-CoA, 3-hydroxyPentanedioic acid (Glutaric acid), glutaconic acid) can accumulate and cause damage to the brain (and also other organs).
Babies with Pentanedioic acid (Glutaric acid)emia type I are often born with unusually large heads (macrocephaly).

Macrocephaly is amongst the earliest signs of GA1.
GA1 also causes secondary carnitine deficiency because Pentanedioic acid (Glutaric acid), like other organic acids, is detoxified by carnitine.

Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis.
Acidosis typically occurs when arterial pH falls below 7.35.

In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy).
These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death.

These are also the characteristic symptoms of untreated Pentanedioic acid (Glutaric acid)uria.
Many affected children with organic acidemias experience intellectual disability or delayed development.

In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures.
Treatment of Pentanedioic acid (Glutaric acid)uria is mainly based on the 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) has also been found in Escherichia
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.

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, Pentanedioic acid (Glutaric acid) is hydrolysed to obtain Pentanedioic acid (Glutaric acid).

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.
Pentanedioic acid (Glutaric acid) 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.

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), with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis and irritable bowel syndrome; Pentanedioic acid (Glutaric acid) has also been linked to several inborn metabolic disorders including Pentanedioic acid (Glutaric acid)uria I, 3-hydroxy-3-methylglutaryl-coa lyase deficiency, and short chain acyl-coa dehydrogenase deficiency.

Pentanedioic acid (Glutaric acid) is a dinucleotide phosphate that exists in two forms: the alpha form, which has a high phase transition temperature and is insoluble in water; and the beta form, which has a low phase transition temperature and is soluble in water.
Pentanedioic acid (Glutaric acid) can be used as an analytical reagent to identify the type of nucleotides present in samples.

Pentanedioic acid (Glutaric acid) can also be used as an experimental solvent for other compounds that are not soluble in water.
The toxicity of Pentanedioic acid (Glutaric acid) has been studied extensively and found to be low.

This compound does not appear to have any adverse effects on human health or animals at doses up to 1g/kg body weight.
Pentanedioic acid (Glutaric acid) has been shown to have anti-infectious properties by inhibiting the growth of bacteria, fungi, and viruses.
The effectiveness of Pentanedioic acid (Glutaric acid) against infectious diseases appears to depend on Pentanedioic acid (Glutaric acid) ability to block protein synthesis by inhibiting enzymes such as glutathione reductase

Pentanedioic acid (Glutaric acid) is the organic compound with the formula C3H6(COOH).
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).
Physical Description of Pentanedioic acid (Glutaric acid):
Pentanedioic acid (Glutaric acid) appears as colorless crystals or white solid.

Pentanedioic acid (Glutaric acid) Formula and Structure:
The chemical formula of Pentanedioic acid (Glutaric acid) is C3H6(COOH)2.
Pentanedioic acid (Glutaric acid) is an alpha, omega-dicarboxylic acid that has linear five-carbon dicarboxylic acid.

In addition, Pentanedioic acid (Glutaric acid) plays a role as a human metabolite and Daphnia Magna metabolite.
Furthermore, Pentanedioic acid (Glutaric acid) is the conjugate acid of glutarate(1- ) and glutamate.
Pentanedioic acid (Glutaric acid) molecular weight is 132.12 g/mol.

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.
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.

Naturally, the body produces Pentanedioic acid (Glutaric acid) during the metabolism of some amino acids that include tryptophan and lysine.
In addition, 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.

Pharmacology and Biochemistry of Pentanedioic acid (Glutaric acid):
Tissue Locations:
Placenta
Prostate

Cellular Locations:
Cytoplasm

Properties of Pentanedioic acid (Glutaric acid):
Pentanedioic acid (Glutaric acid) appears as a colorless crystal or white solid.
Also, Pentanedioic acid (Glutaric acid) boiling point is 303oC or 200oC at 20 mmHg.

On the other hand, Pentanedioic acid (Glutaric acid) melting point is in between 97.5to98oC.
While the relating ‘linear’ dicarboxylic acids adipic and succinic acids are soluble in water only to a few percent at room temperature.

However, Pentanedioic acid (Glutaric acid) is soluble in water and freely soluble in absolute alcohol, ether, benzene, chloroform, and sulfuric acid.
In contrast, Pentanedioic acid (Glutaric acid) is slightly soluble in petroleum ether.
Pentanedioic acid (Glutaric acid) has a density of 1.4 g/cm3.

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 mixed potassium 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.

We can produce Pentanedioic acid (Glutaric acid) by the ring-opening of butyrolactone with potassium cyanide to provide the mixed potassium carboxylate-nitrile that is hydrolyzed to the diacid.
An alternative method is a hydrolysis that is followed by oxidation of dihydropyran that gives Pentanedioic acid (Glutaric acid).
We can also prepare by reacting 1, 3-dibromopropane with sodium or potassium cyanide to acquire the dinitrile followed by hydrolysis.

Applications of Pentanedioic acid (Glutaric acid):
Pentanedioic acid (Glutaric acid) may be employed as starting reagent in the synthesis of glutaric anhydride.
Pentanedioic acid (Glutaric acid) may be used for the following studies:

Complexation with DL-lysine.
Complexes have been reported to possess zwitterionic lysinium ions (positively charged) and semi-glutarate ions (negatively charged).

Synthesis of complexes with L-arginine and L-histidine.
Preparation of glycine-Pentanedioic acid (Glutaric acid) co-crystals.
Phase transition studies of these cocrystals have been reported by single-crystal X-ray diffraction, polarized Raman spectroscopy and differential scanning calorimetry.

Pentanedioic acid (Glutaric acid) 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.

Uses of Pentanedioic acid (Glutaric acid):
We prepare Pentanedioic acid (Glutaric acid) that is a common plasticizer and a precursor to polyesters by hydrogenation of glutamic acid and Pentanedioic acid (Glutaric acid) derivatives.
In addition, we use Pentanedioic acid (Glutaric acid) itself in the production of polymers such as polyamides, and polyols.

Also, the odd number of the carbon atom that is 5 is very useful in decreasing the polymer elasticity.
Moreover, we get uvitonic acid by the action of ammonia on Pentanedioic acid (Glutaric acid).
Hydrogenation of Pentanedioic acid (Glutaric acid) and Pentanedioic acid (Glutaric acid) derivatives produces a placticizers.
Used to produce many polymers such as polyesters, polyamides.

Pentanedioic acid (Glutaric acid), a common plasticizer and precursor to polyesters is manufactured by hydrogenation of Pentanedioic acid (Glutaric acid) and Pentanedioic acid (Glutaric acid) 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.
Uvitonic acid is obtained by the action of ammonia on Pentanedioic acid (Glutaric acid).
Pyrogallol can be produced from glutaric diester.

Buffering
Flavouring
Processing aid not otherwise specified
Processing aids and additives

Industry Uses of Pentanedioic acid (Glutaric acid):
Adsorbents and absorbents
Corrosion inhibitors and anti-scaling agents
Intermediates
Plasticizers
Processing aids, not otherwise listed

Consumer Uses of Pentanedioic acid (Glutaric acid):
Adhesives and sealants
Water treatment products

Methods of manufacturing of Pentanedioic acid (Glutaric acid):
Manufactured from cyclopentanone by oxidative ring fission with hot 50% nitric acid in the presence of vanadium cyanide.
Lab prepn by acid hydrolysis of trimethylene cyanide or of methylenedimalonic ester.
Oxidation of cyclopentanone with 50% nitric acid in the presence of vanadium pentoxide or with air in the presence of a catalyst; by-product in the production of adipic acid from cyclohexane by oxidation with air & nitric acid

Industry Processing Sectors:
All other basic organic chemical manufacturing
Plastic material and resin manufacturing
Utilities

15,000 cu m/hr offgas containing 10-15% sulfur dioxide & 0.5-2 mg h2s/cu m is scrubbed in 4 successive packed columns @ 35 °c with 40-55 cu m/hr 30% aq Pentanedioic acid (Glutaric acid).
A composition for neutralizing or destroying a susceptible virus on infected tissue of a living mammal contains an effective concn of Pentanedioic acid (Glutaric acid) in pharmaceutical vehicle as well as paper or cloth coated or impregnated with the virucide.
Pentanedioic acid (Glutaric acid) may be an essential precursor in the biosynthesis of biotin by a species of agrobacterium.

Solubility of Pentanedioic acid (Glutaric acid):
Soluble in water, alcohol, benzene and chloroform.
Slightly soluble in petroleum ether.

Reactivity Profile of Pentanedioic acid (Glutaric acid):
Glutarıc Acıd is a carboxylic acid.
Carboxylic acids donate hydrogen ions if a base is present to accept them.

They react in this way with all bases, both organic (for example, the amines) and inorganic.
Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat.

Neutralization between an acid and a base produces water plus a salt.
Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water.
Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions.
The pH of solutions of carboxylic acids is therefore less than 7.0.

Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt.
Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt.
Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry.
Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Pentanedioic acid (Glutaric acid) to corrode or dissolve iron, steel, and aluminum parts and containers.

Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide.
The reaction is slower for dry, solid carboxylic acids.
Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide.
Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides.

Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.
Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat.
Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents.
These reactions generate heat.

A wide variety of products is possible.
Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions This compound reacts with bases, oxidizing agents and reducing agents.