| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| Other Sizes |
| Targets |
Human Endogenous Metabolite
No specific drug target identified; acts as a pectin metabolite and may influence gastric mucosal defense mechanisms. |
|---|---|
| ln Vitro |
The solution conformation of digalacturonic acid and its sodium salt have been analyzed using nuclear magnetic resonance data and molecular mechanics calculations. The flexibility around the glycosidic linkage was characterized by calculation of the relaxed (phi, psi) potential surfaces for the isolated molecule, and also for dimethyl sulfoxide and aqueous solutions using the CHARMM and SOLVOL programs. The one-bond and three-bond proton-carbon couplings were measured and H-1'-H-4 distances were estimated from NOESY experiments. The calculated potential surfaces were used to determine theoretical ensemble averages of NMR data. The agreement between the experimental and theoretical data is very satisfactory. The calculations show a strong effect of solvent on the solution behavior of both compounds. The vacuum lowest energy conformer of digalacturonic acid is stabilized by solvation, while for sodium digalacturonate the solvent induces a conformational change. An extrapolation of the stable conformers to polysaccharide chains implies that poly(galacturonic acid) occurs in solution as a three-fold helix and sodium poly(galacturonate) as a two-fold helix [1].
As a metabolite of pectin or pectic acid, digalacturonic acid is used in galacturonic acid metabolism research as a substrate to identify, differentiate, and characterize endo- and exopolygalacturonases and gluconases. It facilitates the co-crystallization of enzymes such as proteinase K, aiding in structural biology studies of these enzymes. |
| ln Vivo |
Digalacturonic acid acts as a therapeutic agent for combating gastric ulcers and enhancing digestion. It demonstrates anti-inflammatory properties and influences the gastric mucosal defense mechanism, making it an effective treatment option for conditions like gastritis and gastroesophageal reflux disease (GERD). It is derived in vivo from pectin catabolism and may contribute to the gastrointestinal benefits associated with dietary pectin.
|
| Enzyme Assay |
Proteinase K, a subtilisin-like fungal protease, was crystallized from a cocktail of small molecules containing digalacturonic acid (DGA). The crystal structure was determined to 1.32 A resolution and refined to an R factor of 0.158. The final model contained, beside the protein, two calcium ions, 379 water molecules, a molecule of DGA and a partially occupied HEPES molecule. The DGA molecule has one sugar moiety disposed exactly on a crystallographic twofold axis; the second ring was not observed. The DGA molecule is bound to two protein molecules across the twofold axis through hydrogen-bonding networks involving Ser150 and water molecules. One of the calcium-ion sites has not been reported previously. This study further illustrates the involvement of small molecules in the crystallization of macromolecules through their ability to form intermolecular lattice interactions [2].
Receptor binding assays are not standard. Enzyme assays using digalacturonic acid as a substrate are performed to characterize polygalacturonase activity. Reaction mixtures contain digalacturonic acid, enzyme source, and buffer (pH 4-5). After incubation at 30-37degC for varying times (15-60 min), reducing sugar release is measured using dinitrosalicylic acid (DNS) reagent or by HPLC analysis of reaction products. |
| Cell Assay |
For cell-based studies, intestinal epithelial cells or gastric cell lines may be treated with digalacturonic acid at concentrations of 0.1-10 mg/mL for 1-24 hours. Markers of inflammation (IL-6, TNF-alpha, COX-2), oxidative stress, and gastric mucosal defense (mucus production, prostaglandin E2) are measured by ELISA or qPCR to assess anti-inflammatory and gastroprotective effects.
|
| Animal Protocol |
In vivo efficacy for gastrointestinal protection is evaluated in rodent models of gastric ulcers. Rats are fasted overnight, then treated with digalacturonic acid (10-100 mg/kg, oral gavage) followed by induction of gastric injury using ethanol, indomethacin, or stress. After 1-4 hours, stomachs are removed and lesion area is measured. Gastric mucosal parameters are analyzed histologically and biochemically.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties specific to digalacturonic acid are not fully characterized. As a disaccharide, it is likely poorly absorbed in the small intestine and may reach the colon intact where it can be fermented by gut microbiota. Systemic bioavailability is expected to be low following oral administration, consistent with other oligosaccharides.
|
| Toxicity/Toxicokinetics |
Toxicity data for digalacturonic acid are limited. Based on its presence as a natural metabolite of dietary pectin, it is generally regarded as safe at normal consumption levels. Standard preclinical safety studies would include acute and repeat-dose oral toxicity in rodents. No significant toxicity has been reported in available literature.
|
| References | |
| Additional Infomation |
α-D-GalpA-(1->4)-D-GalpA is a digalacturonic acid, in which the α-D-pyranogalacturonic acid unit is linked to the D-pyranogalacturonic acid unit via an α-(1->4)-glycosidic bond. It is the conjugate acid of α-D-galacturonic acid (2-). Digalacturonic acid has been reported to be present in common bean (Phaseolus vulgaris), and relevant data are available for reference.
Digalacturonic acid is a naturally occurring metabolite of pectin found in fruits and vegetables. It serves as an important research tool for studying pectin degradation pathways and plant cell wall metabolism. Additionally, it is used in the co-crystallization of enzymes for structural biology studies. This compound is not a drug and has no approved clinical indications, though it has potential applications in gastroenterology as a nutraceutical for gastric health. |
| Molecular Formula |
C12H18O13
|
|---|---|
| Molecular Weight |
370.26
|
| Exact Mass |
370.075
|
| CAS # |
5894-59-7
|
| PubChem CID |
439694
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.97 g/cm3
|
| Boiling Point |
793.8ºC at 760 mmHg
|
| Flash Point |
296.6ºC
|
| Index of Refraction |
1.682
|
| LogP |
-4.2
|
| Hydrogen Bond Donor Count |
8
|
| Hydrogen Bond Acceptor Count |
13
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
25
|
| Complexity |
511
|
| Defined Atom Stereocenter Count |
9
|
| SMILES |
[C@@H]1([C@H]([C@H](O[C@@H]([C@@H]1O)O[C@@H]2[C@@H]([C@H](C(O[C@@H]2C(=O)O)O)O)O)C(=O)O)O)O
|
| InChi Key |
IGSYEZFZPOZFNC-LKIWRGPLSA-N
|
| InChi Code |
InChI=1S/C12H18O13/c13-1-2(14)7(9(18)19)25-12(5(1)17)24-6-3(15)4(16)11(22)23-8(6)10(20)21/h1-8,11-17,22H,(H,18,19)(H,20,21)/t1-,2+,3+,4+,5+,6+,7-,8-,11?,12-/m0/s1
|
| Chemical Name |
(2S,3R,4S,5R,6S)-6-[(2S,3R,4R,5R)-2-carboxy-4,5,6-trihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
|
| Synonyms |
Digalacturonic acid; 5894-59-7; Digalacturonate; C02273; D-4-O-alpha-D-Galactopyranuronosyl-galacturonic Acid;; AC1L97UT; alpha-D-galacturonosyl-(1->4)-D-galacturonate; SureCN13589989;
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7008 mL | 13.5040 mL | 27.0080 mL | |
| 5 mM | 0.5402 mL | 2.7008 mL | 5.4016 mL | |
| 10 mM | 0.2701 mL | 1.3504 mL | 2.7008 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
