ChemicalBook > CAS DataBase List > D-Glucuronic acid

D-Glucuronic acid

Product Name
D-Glucuronic acid
CAS No.
6556-12-3
Chemical Name
D-Glucuronic acid
Synonyms
GLUCURONIC ACID;glucuronate;D-glucuronate;(2S,3S,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoic acid;D-GLCA;Glucosiduronic Acid;Glucuronic Aci;D-GlucuronicAci;Glycuronic acid;D-Glucurono acid
CBNumber
CB9303344
Molecular Formula
C6H10O7
Formula Weight
194.14
MOL File
6556-12-3.mol
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D-Glucuronic acid Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
G5269
Product name
D-Glucuronic acid
Purity
≥98% (GC)
Packaging
10mg
Price
$35
Updated
2024/03/01
Sigma-Aldrich
Product number
8.43961
Product name
D-Glucoronic acid
Purity
for synthese
Packaging
10G
Price
$128
Updated
2024/03/01
Sigma-Aldrich
Product number
8.43961
Product name
D-Glucoronic acid
Purity
for synthese
Packaging
25G
Price
$254
Updated
2024/03/01
Sigma-Aldrich
Product number
1294319
Product name
D-Glucuronic acid
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
50mg
Price
$519
Updated
2024/03/01
TCI Chemical
Product number
G0302
Product name
D-Glucuronic Acid
Purity
>96.0%(HPLC)(T)
Packaging
5g
Price
$38
Updated
2024/03/01
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D-Glucuronic acid Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

Monoglucuronyl glycyrrehetic acid D-Glucurone
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D-Glucuronic acid Suppliers

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View Lastest Price from D-Glucuronic acid manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
D-Glucuronic acid 6556-12-3
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500kgs/month
Release date
2021-07-22
Shanghai Standard Technology Co., Ltd.
Product
D-Glucuronic acid 6556-12-3
Price
US $0.00/mg
Min. Order
20mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2020-04-23
Zhuozhou Wenxi import and Export Co., Ltd
Product
D-GLUCURONIC ACID 6556-12-3
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-11

6556-12-3, D-Glucuronic acidRelated Search:

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

  • GLUCURONIC ACID
  • D-GLCA
  • D-GLUCURONIC ACID
  • Glycuronic acid
  • Glucosiduronic Acid
  • Glucuronic Aci
  • (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid
  • D-GLUCURONIC ACID FREE ACID F & D &
  • Mycophenolic Acid-d3 Methyl Ester 6-Methyl &beta
  • D-Glucuronic acid, 98+%
  • D-glucuronate
  • Glucuronic acid 1g [6556-12-3]
  • (2S,3S,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoic acid
  • D-Glucuronic acid, 98% 10GR
  • D-Glucuronic acid, 98% 25GR
  • D-gluco-Hexulonic acid
  • D-Glucurono acid
  • d-[UL-13C6]glucuronic acid
  • D-Glucuronic acid, free acid
  • D-Glucuronic acid(Glucosiduronic acid)
  • aldehydo-D-glucuronic acid
  • alpha-D-glucuronic acid
  • D-Glucuronic acid, 97.5%
  • D-Glucuronic Acid D
  • Mycophenolic Acid Methyl Ester 6-Methyl &beta
  • 1,2,3,4-Tetra-O-acetyl-&szlig
  • (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid
  • D-GlucuronicAcid&gt
  • D-Glucuronic acid,HPLC≥98%
  • D-GLUCORONIC ACID FOR SYNTHESE
  • glucuronate
  • D-GLUCURONIC ACID USP/EP/BP
  • dextro-glucuronic acid
  • D-Glucuronic Acid extrapure, 98%
  • D-Glucuronic Acid (1294319)
  • α-D-Glucopyranuronic acid
  • D-Glucuronic acid (9CI, ACI)
  • D-GlucuronicAci
  • Glycine impurity 4
  • 6556-12-3
  • 1700-90-8
  • 655-12-3
  • 12/3/6556
  • 1700908
  • 03-十二月-6556
  • C6H10O7
  • Carbohydrate Synthesis
  • BioChemical
  • Biochemicals and Reagents
  • Analytical Enzymes
  • Monosaccharides
  • Enzymes, Inhibitors, and Substrates
  • Specialty Synthesis
  • Related Products
  • 13C & 2H Sugars
  • Biochemistry
  • Glucose
  • Sugars