GLUTARIC ACID
GLUTARIC 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).
EC / List no.: 203-817-2
CAS no.: 110-94-1
Mol. formula: C5H8O4
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.
Glutaric acid (Pentanedioic Acid)is a dicarboxylic acid with five carbon atoms, occurring in plant and animal tissues.
Glutaric acid is found in the blood and urine.
Alpha-ketoglutaric acid, a derivative of glutaric acid which has a ketone group on the carbon atom next to the acid group, is produced from glutamate in amino group and found as an intermediate in the Krebs cycle in the body.
In industrial field, ketoglutaric acid exhibits typical carboxyl group chemistry useful in a variety of industrial applications.
It is a white crystalline solid having has the lowest melting point among dicarboxylic acids (98 C).
It is very soluble in water and the solution is a medium strong acid.
The molecular structure of odd carbon number is also useful to decrease polymer elasticity.
Glutaric acid is used in the production of polyester polyols, polyamides, ester plasticizers and corrosion inhibitors.
It is used in the synthesis of pharmaceuticals, surfactants and metal finishing compounds.
Alpha-ketoglutaric acid is used in dietary supplements to improve protein synthesis.
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.
It can also be prepared from reacting 1,3-dibromopropane with sodium or potassium cyanide to obtain the dinitrile, followed by hydrolysis.
Uses
1,5-Pentanediol, a common plasticizer and precursor to polyesters is manufactured by hydrogenation of glutaric acid and its 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.
Safety
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
Preferred IUPAC name: Pentanedioic acid
Other names
Glutaric acid
Propane-1,3-dicarboxylic acid
1,3-Propanedicarboxylic acid
Pentanedioic acid
n-Pyrotartaric acid
CAS Number: 110-94-1
Chemical formula: C5H8O4
Glutaric acid is an alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.
It has a role as a human metabolite and a Daphnia magna metabolite.
It is a conjugate acid of a glutarate(1-) and a glutarate.
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
Glutaric acid is an alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.
Glutaric acid has a role as a human metabolite and a Daphnia magna metabolite.
Glutaric acid is a conjugate acid of a glutarate(1-) and a glutarate.
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 (PMID: 17465389 , 15505398 ).
Glutaric acid has also been found in Escherichia (PMID: 30143200 ).
1,3-Propanedicarboxylic acid
1,5-Pentanedioic acid
Glutarsaeure
Pentanedioic acid
1,3-Propanedicarboxylate
1,5-Pentanedioate
Pentanedioate
Glutarate
Pentandioate
Pentandioic acid
Chemical Formula: C5H8O4
Average Molecular Weight: 132.1146
Monoisotopic Molecular Weight: 132.042258744
IUPAC Name: pentanedioic acid
Traditional Name: glutaric acid
CAS Registry Number: 110-94-1
Glutaric acid [ACD/IUPAC Name]
1,3-Propanedicarboxylate
1,5-Pentanedioate
1,5-Pentanedioic acid
110-94-1 [RN]
1209725 [Beilstein]
203-817-2 [EINECS]
Acide glutarique [French] [ACD/IUPAC Name]
Glutarsäure [German] [ACD/IUPAC Name]
hydrogen glutarate
MFCD00004410 [MDL number]
n-Pyrotartaric acid
Pentanedioic acid [ACD/Index Name]
1,3-PROPANEDICARBOXYLIC ACID
111-16-0 [RN]
154184-99-3 [RN]
19136-99-3 [RN]
203-817-2MFCD00004410
271-678-5 [EINECS]
273-081-5 [EINECS]
4-02-00-01934 (Beilstein Handbook Reference) [Beilstein]
68603-87-2 [RN]
68937-69-9 [RN]
8065-59-6 [RN]
Glutaric acid (Pentanedioic acid)
glutaric acid, reagent
Gua
http:////www.amadischem.com/proen/581837/
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17859
Pentandioate
Pentandioic acid
pentanedioate
Pentanedioic-2,2,4,4-d4 Acid
Pentanedioic-d6 Acid
Propane-1,3-dicarboxylic acid
Propane-1,3-dicarboxylic acid|Pentanedioic acid,Glutaric acid
WLN: QV3VQ
戊二酸 [Chinese]
Glutaric acid is formed from the catabolism of lysine, hydroxylysine and tryptophan so therapy includes restricting these amino acids from the protein part of the diet.
Glutarate;
Glutaric acid;
Pentanedioic acid;
1,3-Propanedicarboxylic acid
Compounds with biological roles [BR:br08001]
Organic acids
Carboxylic acids
Dicarboxylic acids
C00489 Glutarate
Lipids [BR:br08002]
FA Fatty acyls
FA01 Fatty Acids and Conjugates
FA0117 Dicarboxylic acids
C00489 Pentanedioic acid
Synonyms:
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) is a white crystalline solid which is very soluble in water.
The compound is a useful building block for polymers, an intermediate in chemical synthesis and it is used in the manufacture of an antiretroviral drug.
The compound is also used in solder flux.
In our UK factory, Witton is able to manufacture glutaric acid of high purity that is free from traces of mineral acids and is thus stable when dissolved in alcohols.
The product is supplied as a free flowing white powder packed in plastic kegs with anti-static liners.
Alternative names for glutaric acid include:
1,3-Propanedicarboxylic acid
1,5-Pentanedioic acid
n-Pyrotartaric acid
Pentandioic acid
Pentanedioic acid
Glutaric acid is a 5-carbon aliphatic dicarboxylic acid that possesses several properties.
Glutaric acid has the lowest melting point of all dicarboxylic acids, and is highly soluble in water, making it easy to handle.
Although not registered as an active agent, glutaric acid exhibits virucidal activity.
Other Applications:
· Detergents and cleaners
· Metal finishing
· Resin intermediates
-Polyester polyols
-Polyesters
-Polyamides
1,3-Propanedicarboxylic acid
1,5-Pentanedioic acid
Glutaric acid
Glutaric acid
glutaric acid
n-Pyrotartaric acid
Pentandioic acid
CAS names
Pentanedioic acid
IUPAC names
1,3-Propanedicarboxylic acid
1,5-Pentanedioic acid
CH02923
Glutaric Acid
Glutaric acid
glutaric acid
Glutaric Acid
Glutarsäure
Pentanedioic acid
pentanedioic acid
pentanedioic acid.
Virucidal activity of glutaric acid and evidence for dual mechanism of action.
M F Kuhrt, M J Fancher, M A McKinlay, S D Lennert
ABSTRACT
Rhinoviruses as a group are notably sensitive to inactivation in solutions with a pH of less than 5.3.
Glutaric acid appears to possess virucidal activity in addition to the aciduant effect against rhinoviruses.
A model system in which rhinovirus type 14 was incubated in the presence of glutaric acid (GA) (pH 4.0) at 0 degrees C was devised to separate intrinsic virucidal activity from the aciduant effect.
Under these conditions, virucidal activity against rhinovirus type 14 was directly related to the concentration of GA present and the proportion of the acid in the diprotonated form.
The virucidal activities of GA and several other compounds, including GA analogs and other mono- and dicarboxylic acids, were tested under the conditions described.
In general, as the alkane bridge separating two carboxylic acid functions was lengthened, virucidal activity decreased.
When 26 additional strains of rhinoviruses were tested in the model system, 19 were inactivated slowly enough to be compared.
Applications
Glutaric acid is used as the raw material for organic synthesis, pharmaceutical intermediate and synthetic resin.
It 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.
It acts as an intermediate during the catabolism of lysine in mammals.
Of these, 63% were more susceptible to GA than to sodium acetate buffer and 26% were more susceptible to sodium acetate buffer.
Eleven percent were resistant to both GA and sodium acetate buffer.
The virucidal activity of GA for a majority of strains tested appeared to be due to combination of low pH and another mechanism of action presumably unrelated to pH.
Glutaric Acid
A 5-carbon aliphatic dicarboxylic acid, glutaric acid is produced in the body as an intermediate in lysine, fatty acid, and tryptophan metabolism.
In humans, however, elevated levels of the organic acid can be extremely dangerous and is symptomatic of a relatively rare disorder called glutaric aciduria.
Glutaric acid is used for the manufacture of polyamides and polyesters.
Chemical Formula: C5H8O4
Other names: N-pyrotartaric acid, 1,5-Pentanedioic acid
Layman’s explanation: Glutaric acid is a colorless liquid and white crystals as a solid occurring in plants and animal tissues.
It is used in organic synthesis and as an intermediate for the manufacture of polymers such as polyamides and polyesters, ester plasticizers and corrosion inhibitors.
It is also useful in the application of decreasing polymer elasticity and in a variety of industrial applications.
In addition glutaric acid plays an important role as an intermediary in the Krebs cycle and is used in medication against a large number of viruses and in animal diabetes.
Glutaric acid can be prepared from cyclopentanone by oxidative ring fission with nitric acid and in the presence of a catalyst.
Glutaric acid has the lowest melting point among dicarboxylic acids (98 C); it is very soluble in water and the solution in water is a medium strong acid.
Short-term exposure to glutaric acid may cause irritation to the eyes, skin and the respiratory tract.
Keywords: polymers, polyesters, plasticizers
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).
Other names
Glutaric acid (IUPAC Name); hydrogen glutarate; pentanedioic acid
Description : Isolated from basidiomycete fungi and fruits of Prunus cerasus (CCD).
Glutaric acid is found in many foods, some of which are red beetroot, common beet, soy bean, and tamarind.
1,3-Propanedicarboxylate
1,3-Propanedicarboxylic acid
1,5-Pentanedioate
1,5-Pentanedioic acid
Glutarate
Glutaric acid
Glutarsaeure
Pentandioate
Pentandioic acid
Pentanedioate
1,3-Propanedicarboxylic acid
1,5-Pentanedioic acid
Glutaric acid
Glutaric acid
glutaric acid
n-Pyrotartaric acid
Pentandioic acid
CAS names
Pentanedioic acid
IUPAC names
1,3-Propanedicarboxylic acid
1,5-Pentanedioic acid
CH02923
Glutaric Acid
Glutaric acid
glutaric acid
Glutaric Acid
Glutarsäure
Pentanedioic acid
pentanedioic acid
pentanedioic acid.
GLUTARIC ACID
Pentanedioic acid
110-94-1
1,5-Pentanedioic acid
1,3-Propanedicarboxylic acid
glutarate
Pentandioic acid
n-Pyrotartaric acid
UNII-H849F7N00B
propane-1,3-dicarboxylic acid
CHEBI:17859
Glutaric acid, 99%
HSDB 5542
NSC 9238
EINECS 203-817-2
MFCD00004410
BRN 1209725
AI3-24247
NSC9238
H849F7N00B
DSSTox_CID_1654
DSSTox_RID_76266
DSSTox_GSID_21654
CAS-110-94-1
Glutarsaeure
Pentandioate
Carboxylic acids, C6-18 and C5-15-di-
Carboxylic acids, di-, C4-6
1czc
glutaric acid group
1,5-Pentanedioate
PubChem18989
4lh3
1,3-Propanedicarboxylate
WLN: QV3VQ
(C4-C6) Dibasic acids
bmse000406
SCHEMBL7414
4-02-00-01934 (Beilstein Handbook Reference)
Glutaric acid 110-94-1
KSC178G2T
Pentanedioic acid Glutaric acid
CHEMBL1162495
DTXSID2021654
CTK0H8329
ZINC388706
KS-00000GC3
NSC-9238
Tox21_202448
Tox21_302871
ANW-16215
BBL019768
BDBM50485550
LS-520
s3152
SBB060277
AKOS000118800
CS-W009536
DB03553
HY-W008820
LS41863
MCULE-4286022994
NCGC00249226-01
NCGC00256456-01
NCGC00259997-01
AK114297
AS-13132
BP-21143
H402
SC-16305
100-EP2269610A2
100-EP2277848A1
100-EP2284146A2
100-EP2284147A2
100-EP2287155A1
100-EP2289510A1
100-EP2301924A1
100-EP2305672A1
100-EP2314295A1
100-EP2316457A1
100-EP2316458A1
100-EP2316825A1
100-EP2316826A1
100-EP2316827A1
100-EP2316828A1
100-EP2374780A1
100-EP2374781A1
100-EP2374895A1
FT-0605446
G0069
G0245
H2396
ST51046496
C00489
METHYL5-METHOXY-1H-INDAZOLE-3-CARBOXYLATE
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)
Name Glutaric acid
Synonyms 1,3-Propanedicarboxylic acid
1,5-Pentanedioic acid
Glutaric acid,(Pentanedioic acid
1,3-Propane-dicarboxylic acid)
pentanedioic acid
pentanedioate
CAS 110-94-1
EINECS 203-817-2
Dicarboxylic acid is a compound containing two carboxylic acid, -COOH, groups.
Straight chain examples are shown in table.
The general formula is HOOC(CH2)nCOOH, where oxalic acid’s n is 0, n=1 for malonic acid, n=2 for succinic acid, n=3 for glutaric acid, and etc.
In substitutive nomenclature, their names are formed by adding -dioic’ as a suffix to the name of the parent compound.
They can yield two kinds of salts, as they contain two carboxyl groups in its molecules.
The range of carbon chain lengths is from 2, but the longer than C 24 is very rare.
The term long chain refers to C 12 up to C 24 commonly.
Carboxylic acids have industrial application directly or indirectly through acid halides, esters, salts, and anhydride forms, polymerization, and etc.
Dicarboxylic acids can yield two kinds of salts or esters, as they contain two carboxyl groups in one molecule.
It is useful in a variety of industrial applications include;
Plasticizer for polymers
Biodegradable solvents and lubricants
Engineering plastics
Epoxy curing agent
Adhesive and powder coating
Corrosion inhibitor
Perfumery and pharmaceutical
Electrolyte
There are almost infinite esters obtained from carboxylic acids.
Esters are formed by removal of water from an acid and an alcohol.
Carboxylic acid esters are used as in a variety of direct and indirect applications.
Lower chain esters are used as flavouring base materials, plasticizers, solvent carriers and coupling agents. Higher chain compounds are used as components in metalworking fluids, surfactants, lubricants, detergents, oiling agents, emulsifiers, wetting agents textile treatments and emollients.
They are also used as intermediates for the manufacture of a variety of target compounds.
The almost infinite esters provide a wide range of viscosity, specific gravity, vapor pressure, boiling point, and other physical and chemical properties for the proper application selections.
C length (Straight)
Product
CAS #
Melting Point
Boiling Point
C 2
Oxalic Acid
(Ethanedioic Acid)
144-62-7
189 – 191 C
Sublimes
C 3
Malonic Acid
(Propanedioic Acid)
141-82-2
131 – 135 C
Decomposes
C 4
Succinic Acid
(Butanedioic Acid)
110-15-6
185 – 190 C
235 C
C 5
Glutaric Acid
(Pentanedioic Acid)
110-94-1
95 – 99 C
302 C
C 6
Adipic Acid
(Hexanedioic Acid)
124-04-9
151 – 153 C
265 C at 100 mmHg
C 7
Pimelic Acid
(Heptanedioic Acid)
111-16-0
105 – 106 C
212 C at 10 mmHg
C 8
Suberic Acid
(Octanedioic Acid)
505-48-6
143 – 144 C
230 C at 15 mmHg
C 9
Azelaic Acid
(Nonanedioic Acid)
123-99-9
100 – 103 C
237 C at 15 mmHg
C 10
Sebacic Acid
(Decanedioic Acid)
111-20-6
131 – 134 C
294 at 100 mmHg
C 11
Undecanedioic acid
1852-04-6
109 – 110 C
C 12
Dodecanedioic acid
693-23-2
128 – 129 C
245 C at 10 mmHg
C 13
Brassylic acid
(Tridecanedioic acid)
505-52-2
112 – 114 C
C 14
Tetradecanedioic acid
821-38-5
126 – 128 C
C 15
Pentadecanedioic acid
1460-18-0
C 16
Thapsic acid
(Hexadecanedioic acid)
505-54-4
124 – 126 C
C 18
Octadecanedioic acid
871-70-5