(2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid

Base Information

• Chemical Name: (2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid
• CAS No.: 6556-12-3
• Deprecated CAS: 12758-41-7,36116-79-7,87090-89-9,87246-82-0,36116-79-7,87090-89-9,87246-82-0
• Molecular Formula: C6H10O7
• Molecular Weight: 194.141
• Hs Code.: 2932 99 00
• UNII: 8A5D83Q4RW
• DSSTox Substance ID: DTXSID40273973,DTXSID60859531
• Nikkaji Number: J82.112H
• Wikipedia: Glucuronic_acid
• Wikidata: Q409216
• Metabolomics Workbench ID: 56853
• ChEMBL ID: CHEMBL1235649
• Mol file: 6556-12-3.mol

Synonyms:Glucuronate;Glucuronate, Monopotassium;Glucuronate, Monosodium;Glucuronic Acid;Glucuronic Acid, 6-(14)C-labeled, (D)-isomer;Glucuronic Acid, Monopotassium Salt;Glucuronic Acid, Monosodium Salt;Monopotassium Glucuronate;Monosodium Glucuronate

Chemical Property of (2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 5.45E-08mmHg at 25°C
• Melting Point: 159-161 °C(lit.)
• Refractive Index: 36 ° (C=6, H2O)
• Boiling Point: 495.2 °C at 760 mmHg
• PKA: pKa 3.18(H2O t=20.0) (Uncertain)
• Flash Point: 211.1 °C
• PSA: 135.29000
• Density: 1.987 g/cm³
• LogP: -3.28650
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: H2O: soluble100mg/mL, clear to slightly hazy
• Water Solubility.: Soluble in water.
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 194.04265265
• Heavy Atom Count: 13
• Complexity: 191

Purity/Quality:

98%, ^*data from raw suppliers

D-Glucuronic acid 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(=O)C(C(C(C(C(=O)O)O)O)O)O
• Isomeric SMILES: C(=O)[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O)O)O)O
• 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.
• Uses: 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. 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. 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. 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. D-Glucuronic acid is used as pharmaceutical intermediate and in chemical research.
• 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.UseDetermination 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.GlucuronidasesGlucuronidases are those enzymes that hydrolyze the glycosidic bond between glucuronic acid and some other compound.

Technology Process of (2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid

There total 428 articles about (2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-O-{β-D-apiofuranosyl-(1->4)-[α-L-arabinopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid → D-apiose (639-97-4,6477-44-7,42927-70-8) + D-Galactose (59-23-4) + D-Glucuronic acid (6556-12-3,25249-06-3,25990-10-7,36562-70-6,36655-86-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 100 ℃; for 1h;

DOI:10.1016/S0031-9422(03)00117-1

Reference yield:

3-O-[β-D-apiofuranosyl-(1->4)-β-D-glucuronopyranosyl]oleanolic acid 28-O-β-D-glucopyranosyl ester → D-apiose (639-97-4,6477-44-7,42927-70-8) + D-glucose (50-99-7) + D-Glucuronic acid (6556-12-3,25249-06-3,25990-10-7,36562-70-6,36655-86-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 100 ℃; for 1h;

DOI:10.1016/S0031-9422(03)00117-1

Reference yield:

3-O-{β-D-apiofuranosyl-(1->4)-[α-L-arabinopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid 28-O-β-D-glucopyranosyl ester → D-apiose (639-97-4,6477-44-7,42927-70-8) + L-arabinose (5328-37-0) + D-glucose (50-99-7) + D-Glucuronic acid (6556-12-3,25249-06-3,25990-10-7,36562-70-6,36655-86-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 100 ℃; for 1h;

DOI:10.1016/S0031-9422(03)00117-1

upstream raw materials:

diazomethane

3-O-β-D-galactopyranosyl-(1->2)-<β-D-xylopyranosyl-(1->3)>-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-apiofuranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-<β-D-glucopyranosyl-(1->3)>-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside.

O¹-Propyl-β-D-glucopyranuronsaeure

O¹-Isopropyl-β-D-glucopyranuronsaeure

Downstream raw materials:

O²,O³,O⁴-triacetyl-O¹-((S)-1-benzyl-propyl)-β-D-glucopyranuronic acid methyl ester

O²,O³,O⁴-triacetyl-O¹-((S)-1-phenyl-butyl)-β-D-glucopyranuronic acid methyl ester

O¹-((1R)-trans-1-acetoxy-1,2-dihydro-[2]naphthyl)-O²,O³,O⁴-triacetyl-β-D-glucopyranuronic acid methyl ester

Glucuronsaeure-isoniazon

Refernces

• 1、 Jia, Rui-Bo,Li, Zhao-Rong,Lin, Lianzhu,Luo, Donghui,Ou, Zhi-Rong,Zhao, Mouming,Zheng, Qianwen. "Comparative study on the structural characterization and α-glucosidase inhibitory activity of polysaccharide fractions extracted from Sargassum fusiforme at different pH conditions". . p. 602 - 610. Retrieved 2021/11/30.
• 2、 Vo, Thanh-Hoa,Lin, Yu-Chi,Liaw, Chia-Ching,Pan, Wen-Pin,Cheng, Jing-Jy,Lee, Ching-Kuo,Kuo, Yao-Haur. "Triterpene glycosides and phenylpropane derivatives from Staurogyne concinnula possessing anti-angiogenic activity". . . Retrieved 2021/02/03.