PRODUCTS

GLUTARIC ACID

CAS Number: 110-94-1
EC Number: 203-817-2
Chemical formula: C5H8O4
Molar mass: 132.12 g/mol

Glutaric acid (Pentanedioic Acid) is a linear dicarboxylic acid.
Glutaric acid has been prepared by oxidizing cyclopentane, cyclopentanol and cyclopentanone.

Glutaric acid is a pentanedioic acid.
On exposure to X-rays, glutaric acid crystals generate two stable free radicals.

These free radicals have been investigated by electron nuclear double resonance (ENDOR) technique.
Presence of glutaric acid in urine and plasma is an indicator of type I glutaric aciduria (GA-I).

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 glutaric acid crystal after γ-irradiation is reported to remains trapped in Glutaric acid.
Polymorphism of Glycine-glutaric acid co-crystals has been studied by single crystal X-ray diffraction and Raman spectroscopy.

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

Glutaric acid may cause irritation to the skin and eyes.
When present in sufficiently high levels, 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 glutaric acid are associated with at least three inborn errors of metabolism, including glutaric aciduria type I, malonyl-CoA decarboxylase deficiency, and glutaric aciduria type III.
Glutaric aciduria type I (glutaric acidemia 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. glutaric acid, glutaryl-CoA, 3-hydroxyglutaric acid, glutaconic acid) can accumulate and cause damage to the brain (and also other organs).
Babies with glutaric acidemia 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 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 glutaric aciduria.
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 glutaric aciduria 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 glutaric acid and 3-hydroxyglutaric acid by restriction of natural protein, in general, and of lysine, in particular.
Glutaric acid has also been found in Escherichia

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.

When pentanedioic acid is present in a high amount Glutaric acid acts as a metabotoxin and as an acidogen.
Glutaric acid can be synthesized by the following process

The ring-opening of butyrolactone (C4H6O2) with potassium cyanide (KCN) to produce potassium carboxylate-nitrile.
Glutaric acid is hydrolyzed further to diacid.

Oxidizing dihydropyran will produce glutaric acid.
Glutaric acid can also be synthesized by treating 1,3-dibromopropane with potassium or sodium cyanide to produce dinitrile.
Further, Glutaric acid is hydrolysed to obtain glutaric acid.

Glutaric acid is used as the raw material for organic synthesis, pharmaceutical intermediate and synthetic resin.
Glutaric acid serves as a precursor in the production of polyester polyols, polyamides, ester plasticizers and corrosion inhibitors.

Glutaric acid is useful to decrease polymer elasticity and in the synthesis surfactants and metal finishing compounds.
Glutaric acid acts as an intermediate during the catabolism of lysine in mammals.

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.

Glutaric acid exists in all living organisms, ranging from bacteria to humans.
Glutaric acid is an odorless tasting compound.

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 glutaric acid a potential biomarker for the consumption of these foods.
Glutaric acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis and irritable bowel syndrome; glutaric acid has also been linked to several inborn metabolic disorders including glutaric aciduria I, 3-hydroxy-3-methylglutaryl-coa lyase deficiency, and short chain acyl-coa dehydrogenase deficiency.

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.
Glutaric acid can be used as an analytical reagent to identify the type of nucleotides present in samples.

Glutaric acid can also be used as an experimental solvent for other compounds that are not soluble in water.
The toxicity of 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.
Glutaric acid has been shown to have anti-infectious properties by inhibiting the growth of bacteria, fungi, and viruses.
The effectiveness of glutaric acid against infectious diseases appears to depend on Glutaric acid ability to block protein synthesis by inhibiting enzymes such as glutathione reductase

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 glutaric acid is over 50% (w/w).

Physical Description of Glutaric acid:
Glutaric acid appears as colorless crystals or white solid.

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

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

Biochemistry of Glutaric 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 glutaric aciduria, where toxic byproducts build up and can cause severe encephalopathy.

Naturally, the body produces 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 glutaric aciduria, where toxic byproducts build up and can cause severe encephalopathy.

Pharmacology and Biochemistry of Glutaric acid:

Human Metabolite Information:

Tissue Locations:
Placenta
Prostate

Cellular Locations:
Cytoplasm

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

On the other hand, 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, glutaric acid is soluble in water and freely soluble in absolute alcohol, ether, benzene, chloroform, and sulfuric acid.
In contrast, Glutaric acid is slightly soluble in petroleum ether.
Glutaric acid has a density of 1.4 g/cm3.

Production of Glutaric 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 glutaric 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 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 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 Glutaric acid:
Glutaric acid may be employed as starting reagent in the synthesis of glutaric anhydride.
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-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.

Uses of Glutaric acid:
We prepare 1, 5-Pentanediol that is a common plasticizer and a precursor to polyesters by hydrogenation of glutamic acid and Glutaric acid derivatives.
In addition, we use 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 glutaric acid.

Hydrogenation of glutaric acid and Glutaric acid derivatives produces a placticizers.
Used to produce many polymers such as polyesters, polyamides.

1,5-Pentanediol, a common plasticizer and precursor to polyesters is manufactured by hydrogenation of glutaric acid and Glutaric acid derivatives.
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 glutaric acid.
Pyrogallol can be produced from glutaric diester.

Buffering
Flavouring
Processing aid not otherwise specified
Processing aids and additives

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

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

Methods of manufacturing of 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

General Manufacturing Information of Glutaric 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 glutaric acid.
A composition for neutralizing or destroying a susceptible virus on infected tissue of a living mammal contains an effective concn of glutaric acid in pharmaceutical vehicle as well as paper or cloth coated or impregnated with the virucide.
Glutaric acid may be an essential precursor in the biosynthesis of biotin by a species of agrobacterium.

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

Reactivity Profile of 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 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.

Safety of Glutaric acid:
Glutaric acid may cause irritation to the skin and eyes.
Acute hazards include the fact that this compound may be harmful by ingestion, inhalation or skin absorption.

First Aid of Glutaric acid:
EYES: First check the victim for contact lenses and remove if present.
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center.

Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician.
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing.
Gently wash all affected skin areas thoroughly with soap and water.
If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air.

If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital.
Provide proper respiratory protection to rescuers entering an unknown atmosphere.
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING.
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center.

Be prepared to transport the victim to a hospital if advised by a physician.
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body.

DO NOT INDUCE VOMITING.
IMMEDIATELY transport the victim to a hospital.

Fire Fighting of Glutaric acid:
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher.
A water spray may also be used.

Spillage Disposal of Glutaric acid:
Sweep spilled substance into covered containers.
If appropriate, moisten first to prevent dusting.
Then wash away with plenty of water.

Handling and Storage of Glutaric acid:

Nonfire Spill Response:
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container.
Use absorbent paper dampened with water to pick up any remaining material.

Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal.
Wash all contaminated surfaces with a soap and water solution.
Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should store this chemical at ambient temperatures, and keep Glutaric acid away from oxidizing materials.

Safe Storage of Glutaric acid:
Separated from bases.

Glutaric Acid Health and Safety Hazards:
Glutaric acid can cause irritation to the eyes, respiratory tract, and skin.
The compound has an acute/chronic effects like Glutaric acid is harmful by inhalation, ingestion, or skin absorption.

Also, when heated to decomposition Glutaric acid may emit acrid smoke, toxic fumes of carbon dioxide, and carbon monoxide, and irritating fumes.
If someone inhales Glutaric acid then Glutaric acid can also cause sore throat and cough also Glutaric acid touches the skin or eyes then Glutaric acid causes redness and pain in the area.
Glutaric acid ingestion can cause abdominal pain.

Identifiers of Glutaric acid:
CAS Number: 110-94-1
ChEBI: CHEBI:17859
ChEMBL: ChEMBL1162495
ChemSpider: 723
DrugBank: DB03553
ECHA InfoCard: 100.003.471
EC Number: 203-817-2
KEGG: C00489
PubChem CID: 743
UNII: H849F7N00B
CompTox Dashboard (EPA): DTXSID2021654
InChI:
InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9) check
Key: JFCQEDHGNNZCLN-UHFFFAOYSA-N check
InChI=1/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)
Key: JFCQEDHGNNZCLN-UHFFFAOYAU
SMILES: C(CC(=O)O)CC(=O)O

Properties of Glutaric acid:
Chemical formula: C5H8O4
Molar mass: 132.12 g/mol
Melting point: 95 to 98 °C (203 to 208 °F; 368 to 371 K)
Boiling point: 200 °C (392 °F; 473 K) /20 mmHg

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
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

Physicochemical Information of Glutaric acid:
Boiling point: 302 - 304 °C (1013 hPa) (slow decomposition)
Density: 1.429 g/cm3 (15 °C)
Melting Point: 97.5 - 98 °C
Vapor pressure: 0.022 hPa (18.5 °C)
Solubility: 640 g/l

Specifications of Glutaric acid:
Assay (acidimetric): ≥ 99,0 %(m)
Melting range (lower value): ≥ 95 °C
Melting range (upper value): ≤ 99 °C
Identity (IR): conforms

Names of Glutaric acid:

Preferred IUPAC name of Glutaric acid:
Pentanedioic acid

Other names of Glutaric acid:
Glutaric acid
Propane-1,3-dicarboxylic acid
1,3-Propanedicarboxylic acid
Pentanedioic acid
n-Pyrotartaric acid

Synonyms of Glutaric acid:
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