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

Base Information

• Chemical Name: (2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid
• CAS No.: 685-73-4
• Deprecated CAS: 11100-11-1,444336-16-7,96290-55-0,444336-16-7,552-12-5,96290-55-0
• Molecular Formula: C6H10O7
• Molecular Weight: 194.141
• Hs Code.: 2918990090
• European Community (EC) Number: 211-682-6
• UNII: 2ENU0N1DRP,4JK6RN80GF
• DSSTox Substance ID: DTXSID2042646,DTXSID00873872
• Nikkaji Number: J82.118G
• Wikipedia: D-Galacturonic_acid
• Wikidata: Q422729
• Metabolomics Workbench ID: 38176
• Mol file: 685-73-4.mol

Synonyms:(D)-galacturonic acid;(DL)-galacturonic acid;D-galacturonic acid;DL-galacturonic acid;galacturonic acid;galacturonic acid, (alpha-D)-isomer;galacturonic acid, (D)-isomer;galacturonic acid, calcium, sodium salt, (D)-isomer;galacturonic acid, D-;galacturonic acid, DL-;galacturonic acid, monosodium salt, (D)-isomer

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

Chemical Property:

• Vapor Pressure: 1.49E-14mmHg at 25°C
• Melting Point: 166°C
• Refractive Index: 1.591
• Boiling Point: 553.4 °C at 760 mmHg
• PKA: 3.30±0.35(Predicted)
• Flash Point: 302.6 °C
• PSA: 135.29000
• Density: 1.748 g/cm³
• LogP: -3.28650
• 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

Galacturonicacid 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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: D-Galacturonic acid is a sugar acid, an oxidized form of Dgalactose. It is the main component of pectin, in which it exists as the polymer polygalacturonic acid. It has an aldehyde group at C1 and a carboxylic acid group at C6. Other oxidized forms of D-galactose are D-galactonic acid (carboxylic group at C1) and meso-galactaric acid (mucic acid) (carboxylic groups at C1 and C6). It is also a uronic acid or hexuronic acid. Naturally occurring uronic acids are D-glucuronic acid, D-galacturonic acid, L-iduronic acid and D-mannuronic acid.
• Uses: Biochemical research

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

There total 37 articles about (2S,3R,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:

1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone (20513-98-8) → D-galacturonic acid (576-37-4,685-73-4,1986-14-7,1986-15-8,2073-35-0,3402-98-0,6556-12-3,6814-36-4,14982-50-4,15769-56-9,21675-50-3,21675-51-4,21675-52-5,21675-53-6,27766-62-7,28223-51-0,28223-52-1,39737-41-2,70332-45-5,84710-57-6,102681-51-6,108729-78-8,25249-06-3,25990-10-7,36562-70-6,36655-86-4)

Guidance literature:

With acidic cationen-exchanger; water;

DOI:10.1021/ja01614a072

Reference yield:

[GlcA-Rha]20[IdoA-Rha]6[GlcA-Rha-Xyl]6GlcA26Glc4[SO3-]30 → D-xylose (58-86-6) + L-Rhamnose (3615-41-6,478518-52-4) + D-glucose (50-99-7) + D-Glucuronic acid (6556-12-3,25249-06-3,25990-10-7,36562-70-6,36655-86-4) + D-galacturonic acid (576-37-4,685-73-4,1986-14-7,1986-15-8,2073-35-0,3402-98-0,6556-12-3,6814-36-4,14982-50-4,15769-56-9,21675-50-3,21675-51-4,21675-52-5,21675-53-6,27766-62-7,28223-51-0,28223-52-1,39737-41-2,70332-45-5,84710-57-6,102681-51-6,108729-78-8,25249-06-3,25990-10-7,36562-70-6,36655-86-4)

Guidance literature:

[GlcA-Rha]20[IdoA-Rha]6[GlcA-Rha-Xyl]6GlcA₂₆Glc₄[SO₃-]30; With water; trifluoroacetic acid; at 120 ℃; for 0.75h;

With Helix pomatia β-glucuronidase; at 37 ℃; for 16h; pH=5; aq. acetate buffer; Enzymatic reaction;

DOI:10.1016/j.carbpol.2011.12.041

Reference yield:

[GlcA-Rha]25[IdoA-Rha]6[GlcA-Rha-Xyl]4GlcA24Glc2[SO3-]32 → D-xylose (58-86-6) + L-Rhamnose (3615-41-6,478518-52-4) + D-glucose (50-99-7) + D-Glucuronic acid (6556-12-3,25249-06-3,25990-10-7,36562-70-6,36655-86-4) + D-galacturonic acid (576-37-4,685-73-4,1986-14-7,1986-15-8,2073-35-0,3402-98-0,6556-12-3,6814-36-4,14982-50-4,15769-56-9,21675-50-3,21675-51-4,21675-52-5,21675-53-6,27766-62-7,28223-51-0,28223-52-1,39737-41-2,70332-45-5,84710-57-6,102681-51-6,108729-78-8,25249-06-3,25990-10-7,36562-70-6,36655-86-4)

Guidance literature:

[GlcA-Rha]25[IdoA-Rha]6[GlcA-Rha-Xyl]4GlcA₂₄Glc₂[SO₃-]32; With water; trifluoroacetic acid; at 120 ℃; for 0.75h;

With Helix pomatia β-glucuronidase; at 37 ℃; for 16h; pH=5; aq. acetate buffer; Enzymatic reaction;

DOI:10.1016/j.carbpol.2011.12.041

upstream raw materials:

1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone

α-D-GalpA-(1->2)-Glycerol

5-keto-L-galactonic acid

water

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

6-(4-bromo-phenylhydrazono)-6-deoxy-L-galactonic acid-(4-bromo-phenylhydrazide)

Refernces

• 1、 Meng, Ting,Yu, Sha-sha,Ji, Hai-yu,Xu, Xiao-meng,Liu, An-jun. "A novel acid polysaccharide from Boletus edulis: extraction, characteristics and antitumor activities in vitro". . p. 13 - 24. Retrieved 2021/02/01.
• 2、 Cheng, Jiang,Deng, Yejun,Huang, Lixin,Liu, Lujie,Wang, Xiang,Xie, Pujun,Zhang, Caihong. "Novel polysaccharide from Chaenomeles speciosa seeds: Structural characterization, α-amylase and α-glucosidase inhibitory activity evaluation". . p. 755 - 766. Retrieved 2020/03/18.