(2S,3R,4R,5R,6S)-6-(((1S,2R,3R,4R)-1-Carboxy-1,3,4-trihydroxy-5-oxopentan-2-yl)oxy)-3-(((2S,3R,4R,5R,6S)-6-carboxy-5-(((2S,3R,4S,5R,6S)-6-carboxy-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-4,5-dihydroxytetrahydro-2H-pyran-2-carboxylic acid
Basic information
- CAS
24008-75-1- Standard SMILES
O=C[C@H](O)[C@@H](O)[C@@H](O[C@H]1O[C@H](C(=O)O)[C@H](O[C@H]2O[C@H](C(=O)O)[C@H](O[C@H]3O[C@H](C(=O)O)[C@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)[C@H](O)C(=O)O- InChIKey
RBRHDCQVRHFXDQ-HBMLPAGBSA-N- Molecular formula
- C24H34O25
- Average molar mass
- 722.5 g/mol
- Monoisotopic mass
- 722.13891657
Names & identifiers
- Preferred name
- (2S,3R,4R,5R,6S)-6-(((1S,2R,3R,4R)-1-Carboxy-1,3,4-trihydroxy-5-oxopentan-2-yl)oxy)-3-(((2S,3R,4R,5R,6S)-6-carboxy-5-(((2S,3R,4S,5R,6S)-6-carboxy-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-4,5-dihydroxytetrahydro-2H-pyran-2-carboxylic acid
- IUPAC
- (2S,3R,4S,5R,6S)-6-[(2S,3R,4R,5R,6S)-2-carboxy-6-[(2S,3R,4R,5R,6S)-2-carboxy-6-[(1S,2R,3R,4R)-1-carboxy-1,3,4-trihydroxy-5-oxopentan-2-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
- English name
- Tetragalacturonic Acid
- Molecular formula
- C24H34O25
- Molecular weight
- 722.51
Names & synonyms
(2S,3R,4R,5R,6S)-6-(((1S,2R,3R,4R)-1-Carboxy-1,3,4-trihydroxy-5-oxopentan-2-yl)oxy)-3-(((2S,3R,4R,5R,6S)-6-carboxy-5-(((2S,3R,4S,5R,6S)-6-carboxy-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-4,5-dihydroxytetrahydro-2H-pyran-2-carboxylic acidorb2941330TSW-00702HY-W743822Tetragalacturonic AcidGalacturonan oligosaccharide DP4 (>50% HPAEC-PAD) Sodium saltD-Galacturonic acid, O-α-D-galactopyranuronosyl-(1→4)-O-α-D-galactopyranuronosyl-(1→4)-O-α-D-galactopyranuronosyl-(1→4)-
Database identifiers
- CAS
24008-75-1- PubChem CID
- 168440849
Properties
Computed structural properties
- XLogP
- -8.3
- Topological polar surface area
- 424 Ų
- Hydrogen bond donors
- 14
- Hydrogen bond acceptors
- 25
- Rotatable bonds
- 14
- Heavy atoms
- 49
- Formal charge
- 0
- Complexity
- 1,200
Physicochemical properties
- Melting point
- 132 °C · >132°C (dec.)
- Boiling point
- 1238.5 · 1238.5±65.0 °C(Predicted)
- Density
- 2.01 · 2.01±0.1 g/cm3(Predicted)
- storage temp.
- Hygroscopic, Refrigerator, under inert atmosphere
- solubility
- Aqueous (Slightly), Methanol (Very Slightly, Heated), Water (Slightly)
- pka
- 2.66 · 2.66±0.70(Predicted)
- form
- Solid
- color
- White to Off-White
Chemistry & industry
Applications
UsesTetragalacturonic Acid, is the product of polygalacturonic acid degradation. The mixture of Oligogalacturonic Acids has shown to have shoot growth in cockscomb (Celosia argentea L.) seedlings.
Additional notes
DefinitionChEBI: Alpha-D-GalpA-(1->4)-alpha-D-GalpA-(1->4)-alpha-D-GalpA-(1->4)-alpha-D-GalpA is a tetraisaccharide in which four alpha-D-galactopyranuronic acid units are joined via (1->4)-linkages. It has a role as a bacterial xenobiotic metabolite. It is a carbohydrate acid and a tetrasaccharide.
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