D-Glucuronic acid Chemical Properties

Melting point:

159-161 °C (lit.)

Boiling point:

250.56°C (rough estimate)

alpha 

[α]D20 +35.0～+39.0゜(c=6,H2O)

Density 

1.4301 (rough estimate)

refractive index 

36 ° (C=6, H2O)

storage temp. 

-20°C

solubility 

H2O: soluble100mg/mL, clear to slightly hazy

form 

Crystalline Powder

pka

pKa 3.18(H2O t=20.0) (Uncertain)

color 

White to off-white

Water Solubility 

Soluble in water.

Merck 

14,4465

BRN 

1727083

Stability:

Hygroscopic

InChIKey

LCUVNMXNGSEBHT-RJOKPDHXSA-N

CAS DataBase Reference

6556-12-3(CAS DataBase Reference)

EPA Substance Registry System

D-Glucuronic acid (6556-12-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36

WGK Germany 

3

RTECS 

LZ8836600

TSCA 

Yes

HS Code 

2932 99 00

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

D-Glucuronic acid Usage And Synthesis

Description

Glucuronic acid (from Ancient Greek γλυκ?? "sweet" + ο?ρον "urine") is a carboxylic acid. Its structure is similar to that of glucose. However, glucuronic acid's sixth carbon is oxidized to a carboxylic acid. Its formula is C₆H₁₀O₇. The salts and esters of glucuronic acid are known as glucuronates; the anion C₆H₉O₇^-is the glucuronate ion.

Chemical Properties

White Solid

Uses

D-Glucuronic acid is used as pharmaceutical intermediate and in chemical research.

Uses

1. D-Glucuronic acid is widely distributed in the plant and animal kingdoms. D-Glucuronic acid usually occurs in "paired" form as a glycosidic combination with phenols, alcohols. Such glucuronides form in the liver to detoxify poisonous hydroxyl-containing substances. The glucuronides present in normal urine are those of phenol, cresol, and indoxyl. After the ingestion of poisons such as morphine, chloral hydrate, camphor, or turpentine, glucuronides formed with the poison or its hydroxylated derivatives appear in the urine.
2. Chiral D-Glucuronic acid is a basic building block of hyaluronic acid and chondroitin sulfate. It is a precursor to vitamin C, the chief detoxifying agent in plants and animals.
3. D-Glucuronic Acid is a sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.

Uses

D-glucuronic acid and D-galacturonic acid are naturally occurring hexuronic acids present in glycosaminoglucans, glucuronide conjugates in mammals and in plant cell wall polysaccharides.
D-Glucuronic acid exists as a component of glycosaminoglucans such as hyaluronan, heparin and chondroitin sulphate present in mammalian connective tissue such as cartilage. In the synthesis of glucuronide conjugates in mammals glucuronic acid is conjugated to xenobiotic compounds, a biosynthesis reaction known as glucuronidation, catalysed by the enzyme UDP-glucuronyltransferase and considered a detoxifying process.
Both D-glucuronic acid and D-galacturonic acid are major components of plant cell wall polysaccharides. D-glucuronic acid is a component of arabinoxylan, which consists of a β-(1,4)-linked xylan backbone substituted with α-(1-2/3)-linked L-arabinofuranose and α-(1-2)- linked 4-O-methylglucuronic acid. D-Galacturonic acid is the major component of pectin comprising the α-(1,4)-linked galacturonan backbone of homogalacturonan and rhamnogalacturonan II, and is present within the repeating disaccharide unit [,4)-α-D-GalpA-(1,2)-α- L-Rhap-(1,] of rhamnogalacturonan I.

Definition

ChEBI: A D-glucopyranuronic acid in which the anomeric centre has alpha-configuration.

Definition

glucuronic acid: A compound,OC₆H₉O₆, derived from the oxidationof glucose. It is an important constituentof gums and mucilages. Glucuronicacid can combine withhydroxyl (–OH), carboxyl (–COOH), oramino (-NH₂) groups to form a glucuronide.The addition of a glucuronidegroup to a molecule(glucuronidation) generally increasesthe solubility of a compound; henceglucuronidation plays an importantrole in the excretion of foreign substances.

Biological Functions

Proteoglycans Glucuronic acid is common in carbohydrate chains of proteoglycans. It is part of mucous animal secretions (such as saliva), cell glycocalyx and intercellular matrix (for instance hyaluronan))
Glucuronidation of toxic substances
In the animal body, glucuronic acid is often linked to the xenobiotic metabolism of substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids. These linkages involve glycosidic bonds, and this linkage process is known as glucuronidation. Glucuronidation occurs mainly in the liver, although the enzyme responsible for its catalysis, UDP-glucuronyltransferase, has been found in all major body organs, e.g., intestine, kidneys, brain, adrenal gland, spleen, and thymus.
Use
Determination of urinary steroids and of steroid conjugates in blood. Contained in some commercially available brands of Kombucha as an antioxidant & organic acid In all plants and mammals - other than guinea pigs and primatesglucuronic acid is a precursor of ascorbic acid , also known as vitamin c.
ConformationUnlike its C5 epimer iduronic acid, which may occur in a number of conformations, glucuronic acid occurs in predominantly the ⁴C₁ conformation.
Glucuronidases
Glucuronidases are those enzymes that hydrolyze the glycosidic bond between glucuronic acid and some other compound.

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Biochem/physiol Actions

In humans, glucuronic acid conjugation with steroidal compounds and drugs is an important step in phase II metabolic reactions. This influences the biotransformation process of the compound.

Purification Methods

Crystallise the acid from EtOH or EtOAc, wash it with MeOH and dry it in vacuo to give the “ ” form. Heating converts it to the lactone (see below). The sodium salt monohydrate [207300-70-7] M 234.1 has m ~136-138o(dec) [] D 20 +21o (c 2, H2O after 2hours). [Sutter & Reichstein Helv Chim Acta 21 1210 1938, Beilstein 3 H 886, 3 IV 1997.]

D-Glucuronic acid(6556-12-3)Related Product Information

• URIDINE-5'-DIPHOSPHO-GLUCURONIC ACID, TRISODIUM SALT 98-100%,URIDINE-5'-DIPHOSPHO-GLUCURONIC ACID, TRISODIUM SALT 98-100%
• D-Glucurone
• D-Glucuronic acid sodium salt
• 2,3,4-TRI-O-ACETYL-BETA-D-GLUCURONIC ACID METHYL ESTER,2,3,4-TRI-O-ACETYL-BETA-D-GLUCURONIC ACID METHYL ESTER
• Chondroitin sulfate A sodium salt
• D-GLUCURONIC ACID SODIUM CELL*CULTURE TE STED,D-GLUCURONIC ACID SODIUM,D-GLUCURONIC ACID SODIUM CELL*CULTURE TE STED,D-GLUCURONIC ACID SODIUM
• alternating copoly(β-glucuronic acid-[1→3]-β-n-acetylglucosamine-[1→4]),alternating copoly(β-glucuronic acid-[1→3]-β-n-acetylglucosamine-[1→4])
• D-(+)Glucuronic acid
• 1,2,3,4-TETRA-O-ACETYL-A,BETA-D-GLUCURONIC ACID, METHYL ESTER,1,2,3,4-TETRA-O-ACETYL-A,BETA-D-GLUCURONIC ACID, METHYL ESTER
• 6-BROMO-2-NAPHTHYL-BETA-D-GLUCURONIC ACID,6-BROMO-2-NAPHTHYL-BETA-D-GLUCURONIC ACID
• ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER
• Uridine diphosphate glucuronic acid,Uridine diphosphate glucuronic acid
• PHENOLPHTHALEIN GLUCURONIC ACID
• L-Glucurono-3,6-lactone
• 1,2,3,4-Tetra-O-acetyl-b-D-glucuronic Acid,1,2,3,4-Tetra-O-acetyl-b-D-glucuronic Acid
• D-Glucuronic Acid Phenylmethyl Ester,Glucuronic Acid Benzyl Ester,D-Glucuronic Acid Phenylmethyl Ester,Glucuronic Acid Benzyl Ester
• 1,2,3,4-Tetra-O-acetyl-a,b-D-glucuronic Acid, Methyl Ester (mixture of anomers),1,2,3,4-Tetra-O-acetyl-a,b-D-glucuronic Acid, Methyl Ester (mixture of anomers)
• Methyl 2,3,4-Tri-O-acetyl-b-D-glucuronic Acid Methyl Ester,Methyl 2,3,4-Tri-O-acetyl-b-D-glucuronic Acid Methyl Ester