GLUCURONIC ACID

CAS NO:528-16-5
EC NO:208-429-7

Glucuronic acid is a uronic acid that was first isolated from urine (hence the name).
Glucuronic acid is found in many gums such as gum arabic (c. 18%), xanthan, and Kombucha tea and is important for the metabolism of microorganisms, plants and animals.

Uses of Glucuronic acid
Determination of urinary steroids and of steroid conjugates in blood. Ethyl glucuronide and ethyl sulfate are excreted in urine as metabolites of ethanol and are used to monitor alcohol use or dependence.

Glucuronic acid and gluconic acid are fermentation products in Kombucha tea.

Glucuronic acid is a precursor of ascorbic acid (vitamin C, formerly called L-hexuronic acid). Ascorbate can be biosynthesized by higher plants, algae, yeast and most animals. An adult goat produces ~13 g of vitamin C per day. This ability is lacking in some mammals (including humans and guinea pigs) and also in insects, invertebrates and most fishes. These species require external ascorbate supply, because they lack the biosynthetic enzyme L-gulonolactone oxidase.

The glucuronide 4-methylumbelliferyl-β-D-glucuronide (MUG) is used to test for the presence of Escherichia coli. E. coli produces the enzyme β-glucuronidase, which hydrolyzes the MUG molecule to a fluorescent product that is detectable under ultraviolet light.

Glucuronic acid (C6H10O7), a derivative of glucose, is produced in the liver of humans and most animals. 
Glucuronic acid is a highly soluble compound that can bind to substances such as hormones, drugs, and toxins to facilitate their transport around the body. In this way glucuronic acid is largely responsible for the elimination of poisonous substances such as PCBs.

General description
Glucuronic acid is one of the component of xylan backbone, a hemicellulose present in plant cell wall.

Application
Glucuronic acid has been used:
in in vitro human digestion model
as a fibrous cellulose powder, to test the feeding preference among experimental termites
as a standard to quantify glucuronic acid in urine sample

Glucuronic acid is a D-glucuronic acid in cyclic pyranose form. 
Glucuronic acid has a role as an algal metabolite. 
Glucuronic acid is a conjugate acid of a D-glucopyranuronate.
Glucuronic acid is an enantiomer of a L-glucopyranuronic acid.
Glucuronic acid (CAS: 6556-12-3) is a carboxylic acid that has the structure of a glucose molecule that has had its sixth carbon atom (of six total) oxidized. 
The salts of glucuronic acid are known as glucuronates. 
Glucuronic acid is highly soluble in water. In humans, glucuronic acid is often linked to toxic or poisonous substances to allow for subsequent elimination, and to hormones to allow for easier transport. These linkages involve O-glycosidic bonds.
Glucuronic acid  is known as glucuronidation, and the resulting substances are known as glucuronides (or glucuronosides). 
Glucuronic acid  uses UDP-glucuronic acid (glucuronic acid linked via a glycosidic bond to uridine diphosphate) as an intermediate. UDP-glucuronic acid is formed in the liver of all animals.
Glucuronic acid and the harmful substance combine in the liver and then are passed in the urine.

A carboxylic acid with structural similarity to glucose with detoxifying activity. The xenobiotic metabolism of various substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids involves glucuronidation, a process in which water-soluble, excretable glucuronides of these substances are formed via glycosidic linkages to glucuronic acid. 
Glucuronic acid, formed in the liver through the linkage of glucuronic acid to uridine diphosphate (UDP) via a glycosidic bond, is an intermediate in the process of glucuronidation.
Glucuronic acid is an electrolyte supplement used in total parenteral nutrition.

A nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. 
Glucuronic acid may also be epimerized to UDP iduronic acid, which donates iduronic acid to polysaccharides. In animals, Glucuronic acid is used for formation of many glucosiduronides with various aglycones.

Glucuronic acid is a mild organic acid derived from glucose by a simple oxidation reac-tion. The reaction is facilitated by the enzyme glucose oxidase (fungi) and glucose de-hydrogenase (bacteria such as Gluconobacter). Microbial production of Glucuronic acid is the preferred method and it dates back to several decades. The most studied and widely used fermentation process involves the fungus Aspergillus niger. 
Glucuronic acid and its deriva-tives, the principal being sodium gluconate, have wide applications in food and pharma-ceutical industry.

Glucuronic acid is a mild organic acid, neither caustic nor corrosive and with an excellent sequestering power. Non-toxic and readily biodegradable (98 % after 2 days), it occurs naturally in plants, fruits and other foodstuffs such as wine (up to 0.25 %) and honey (up to 1 %). 

Glucuronic acid has versatile properties through being a polyhydroxycarboxylic acid, with both hydroxyl and carboxyl groups which can react.

Concentrated solutions of Glucuronic acid contain some lactone (GdL), the neutral cyclic ester, which is less soluble in the cold and possesses no actual acid properties. About 5 % of GdL are present in the Glucuronic acid solution at room temperature.

The outstanding property of Glucuronic acid is its excellent chelating power, especially in alkaline and concentrated alkaline solutions. In this respect, it surpasses all other chelating agents, such as EDTA, NTA and related compounds. Calcium, iron, copper, aluminium and other heavy metals are firmly chelated in alkaline solution and masked in such a way that their interferences are eliminated.

Glucuronic acid is stable at the boiling point even of concentrated alkaline solutions. However, it is easily and totally degraded in waste water treatment plants (98 % after 2 days).

Glucuronic acid is a mild organic acid derived from glucose by a simple oxidation reaction. The reaction is facilitated by the enzyme glucose oxidase (fungi) and glucose dehydrogenase (bacteria such as Gluconobacter). Microbial production of Glucuronic acid is the
preferred method and it dates back to several decades. The most studied and widely used
fermentation process involves the fungus Aspergillus niger. 
Glucuronic acid and its derivatives, the principal being sodium gluconate, have wide applications in food and pharmaceutical industry. 

Glucuronic acid is a carboxylic acid that has the structure of a glucose molecule that has had its sixth carbon atom (of six total) oxidized. The salts of glucuronic acid are known as glucuronates. 
Glucuronic acid is highly soluble in water. In the animal body, glucuronic acid is often linked to poisonous substances to allow for subsequent elimination, and to hormones to allow for easier transport. These linkages involve O-glycosidic bonds. 
Glucuronic acid is known as glucuronidation, and the resulting substances are known as glucuronides (or glucuronosides). 
Glucuronidation uses UDP-glucuronic acid (glucuronic acid linked via a glycosidic bond to uridine diphosphate) as an intermediate. 
Glucuronic acid is formed in the liver of all animals. [HMDB] Widely distributed in plants, where it occurs in gums, mucilages, saponins and flavone glycosides and in animals as a constituent of mucopolysaccharides. 
Glucuronic acid are formed in the liver to detoxify poisonous hydroxyl-containing substances. Phenyl, cresyl and indoxyl glycosides are present in normal urine. [CCD]. 
Glucuronic acid is found in many foods, some of which are cashew nut, american cranberry, sour cherry, and soy bean.

Belongs to the class of organic compounds known as glucuronic acid derivatives. 
Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Glucuronic acid is a water-soluble organic acid that belongs to the hydroxycarboxylic acid family. 
Glucuronic acid is an oxidation product of glucose that occurs widely in nature, and is present in fruit, wine, honey, and other natural sources. The chemical structure of  Glucuronic acid of a six-carbon chain with five hydroxyl (-OH) groups terminating in a carboxylic acid group. The close proximity of the oxygen atoms within the chemical structure lends to its function as a highly efficient chelating agent. Chelating agents bind to positively charged metal ions in solution and thereby prevent them from forming insoluble precipitates with other ions that may be present. 
Glucuronic acid acid functions as a chelating agent over a wide pH range. 
Glucuronic acid is efficient in forming stable chelates with divalent and trivalent metal ions such as calcium, copper, iron, aluminum, and other metals, reducing the adverse effects these metals can have on systems.
Glucuronic acid also acts as a humectant, which means that it attracts water and increases hydration in products. 
Glucuronic acid is used as a high performing chelating agent, processing aid, and humectant in a variety of applications and product sectors.

Glucuronic acid, a mild organic acid derived from sugar, mainly used as an acidity regulator and chelating agent in food with the European food additive number E574. This ingredient is also used to produce gluconates (E576, 577, 578, 579, 585) and glucono delta-lactone (E575) to be used in different food applications and other fields.

How is Glucuronic acid made?
Generally, Glucuronic acid is produced by oxidation of D-glucose (derived from starch hydrolysis) with different manufacturing processes :

Bromine water
Microorganisms, such as Aspergillus niger and Acetobactor suboxydans  Enzymes derived from microorganisms 

What’re the Uses of Glucuronic acid?
Mainly used for its leavening and acidity properties in food; chelating and perfuming agents in cosmetics products; also it can be used in industrial uses for chelating heavy metals.

Food
The following food may contain with Glucuronic acid:

Bakery goods: as a leavening acid in leavening agent to increase dough volume by producing gas by the reaction with baking soda.
Dairy products: as a chelating agent and prevent milkstone.
Some food and beverage: as an acidity regulator to impart a mild organic acid and adjust pH level and also as a preservative and an antifungal agent. Also, it can be used to clean aluminium cans.

Animal Nutrition
Glucuronic acid functions as a weak acid in piglet feed, poultry feed and aquaculture to comfort digestive and promote growth, also to increase the production of butyric acid and SCFA (Short-chain fatty acid). 

Cosmetics
Glucuronic acid can be used as a chelating and perfuming agent in cosmetic and personal care products. 

Industrial uses 
The power of chelating heavy metals is stronger than that of EDTA, such as the chelation of calcium, iron, copper, and aluminium in alkaline conditions. 
Glucuronic acid can be utilized in detergents, electroplating, textiles and so on.

Glucuronic acid, the oxidation product of glucose, is a mild neither caustic nor corrosive, non toxic and readily biodegradable organic acid of great interest for many applications. As a multifunctional carbonic acid belonging to the bulk chemicals and due to its physiological and chemical characteristics,Glucuronic acid itself, its salts (e.g. alkali metal salts, in especially sodium gluconate) and the gluconolactone form have found extensively versatile uses in the chemical, pharmaceutical, food, construction and other industries. 
Present review article presents the comprehensive information of patent bibliography for the production of Glucuronic acid and compares the advantages and disadvantages of known processes. 
Numerous manufacturing processes are described in the international bibliography and patent literature of the last 100 years for the production of Glucuronic acid from glucose, including chemical and electrochemical catalysis, enzymatic biocatalysis by free or immobilized enzymes in specialized enzyme bioreactors as well as discontinuous and continuous fermentation processes using free growing or immobilized cells of various microorganisms, including bacteria, yeast-like fungi and fungi. 
Alternatively, new superior fermentation processes have been developed and extensively described for the continuous and discontinuous production of Glucuronic acid by isolated strains of yeast-like mold Aureobasidium pullulans, offering numerous advantages over the traditional discontinuous fungi processes.

The many uses of Glucuronic acid and some of its salts are arousing increasing interest in these compounds and in their production levels. Although Glucuronic acid and gluconates can be obtained chemically, they are currently almost exclusively biotechnologically produced, mostly by fungus based methods. 
There is, however, an ongoing search for alternative microorganisms to avoid the problems of using fungi for this purpose and to improve the productivity of the process. Especially promising in this respect are acetic acid bacteria, particularly Gluconobacter strains.

DESCRIPTION:
Glucuronic acid is composed of an equilibrium between the free acid and the two lactones. This equilibrium is affected by the mixture's concentration and temperature. A high concentration of the delta-lactone will favor the equilibrium to shift to the formation of gamma-lactone and vice versa.
 A low temperature favors formation of glucono-delta-lactone while high temperatures will increase formation of glucono-gamma-lactone. Under normal conditions, PMP Glucuronic acid exhibits a stable equilibrium contributing to its clear to light yellow color with low level corrosiveness and toxicity.

APPLICATION:
Glucuronic acid has versatile properties through being a polyhydroxycarboxylic acid, with both hydroxyl and carboxyl groups which can react.

Concentrated solutions of Glucuronic acid contain some lactone (GDL), the neutral cyclic ester, which is less soluble in the cold and possesses no actual acid properties. About 5 % of GdL are present in the Glucuronic acid solution at room temperature.

The outstanding property of Glucuronic acid is its excellent chelating power, especially in alkaline and concentrated alkaline solutions. In this respect, it surpasses all other chelating agents, such as EDTA, NTA and related compounds. Calcium, iron, copper, aluminum and other heavy metals are firmly chelated in alkaline solution and masked in such a way that their interferences are eliminated.

Glucuronic acid is stable at the boiling point even of concentrated alkaline solutions. However, it is easily and totally degraded in waste water treatment plants .

Application
Glucuronic acid sodium salt has been used:
Glucuronic acid as a component to make synthetic interstitial fluid.
Glucuronic acid used as a carbohydrate.
Glucuronic acid used as a substitute for sodium chloride to make chlorine (Cl-) free media.

Glucuronic acid is one of the most essential natural acids and is moderately obtained from glucose by unpretentious oxidation response process. 
Glucuronic acid is simplified through glucose dehydrogenase bacteria such as (Gluconobacter) and enzyme glucose oxidase (fungi).
Glucuronic acid by microbes is the desired procedure. The typical broadly applied fermentation technique is summarized by using fungi (Aspergillus niger). Derivatives for Glucuronic acid; the main ones like sodium gluconate, have big implementations in the agricultural and food industries. 
Glucuronic acid is used in many applications in pharmaceuticals, food, textile, cement industries, metal chelating agent, leather, beverages and dairy. 
Glucuronic acid produced by fermentation process include fungi is well established commercially. Therefore the mechanism of fermentation processes, efficient microorganism are used to give high yields, more economical process, efficient conversion of carbon sources from cheap substrates for production Glucuronic acid with more yield and quality.

Glucuronic acid was originally petitioned for use as a coagulant in tofu production.
Glucuronic acid can be used in production of “silken” tofu (which has a yogurt-like consistency) by mixing with hot soy milk directly into retail containers. 
Glucuronic acid reduces the chance of microbial fermentation and extends the product’s shelf life.

Glucuronic acid has several other applications in food production because of its acidic and chelating properties. 
Glucuronic acid is used as an acidifier in the production of dairy products that require a slow reduction in pH, such as cottage cheese, feta cheese and mozzarella. 
Glucuronic acid is also used as an acidifier in salad dressings and ready-to-eat pasta and rice. Glucono delta-lactone is used as curing agent in processed meat products. 
Glucuronic acid is also used as a leavening agent in bread and pastries, and causes a slower rate of carbon dioxide release compared to other leavening agents. All of these Generally Recognized as Safe (GRAS) applications of glucono delta-lactone are allowed in organic food processing.

CAS Number
528-16-5
Molecular Formula
C6H10O7
Molecular Weight
194.14
Chemical Purity
Min. 98% [1H-NMR]
Appearance
White Crystalline Solid
Melting Point
166-168 °C

IUPAC names
(2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid

SYNONYMS:
Glucuronic acid [Wiki]
18968-14-4 [RN]
229-486-4 [EINECS]
576-37-4 [RN]
8A5D83Q4RW
Acide D-glucuronique [French] [ACD/IUPAC Name]
D-(+)-glucuronic acid
D-(+)GLUCURONIC ACID
D-Glucuronic acid [ACD/Index Name] [ACD/IUPAC Name]
D-Glucuronsäure [German] [ACD/IUPAC Name]
(2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid
(2S,3S,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoicacid
12758-41-7 [RN]
1700-90-8 [RN]
1727083 [Beilstein]
2050314 [Beilstein]
229-486-4MFCD00077778
36116-79-7 [RN]
63074-07-7 [RN]
6556123
87090-89-9 [RN]
87246-82-0 [RN]
aldehydo-D-glucuronate
aldehydo-D-glucuronic acid
d(+)-glucuronic acid
D(+)-glucuronicacid
D020723
d-glucuronic acid, 98%
d-glucuronic acid, free acid
D-GLUCURONICACID