| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
|
||
| Other Sizes |
| Targets |
Microbial Metabolite Human Endogenous Metabolite
Microbial aromatic degradation pathways (the beta-ketoadipate pathway). Cis,cis-muconic acid is a key intermediate in the ortho-cleavage pathway of catechol, catalyzed by catechol 1,2-dioxygenase. It is also a substrate for muconate cycloisomerase. |
|---|---|
| ln Vitro |
The compound itself has no pharmacological activity in mammalian cells. In bacterial assays, it serves as a carbon source and induces the expression of genes involved in aromatic compound degradation. It is not cytotoxic at low millimolar concentrations.
|
| ln Vivo |
No in vivo activity in animals is reported. In humans, cis,cis-muconic acid is a urinary biomarker of benzene exposure; its excretion reflects the degree of exposure. It is not used as a therapeutic agent.
|
| Enzyme Assay |
A non-cell assay for catechol 1,2-dioxygenase is performed. Cell lysates or purified enzyme are incubated with catechol (0.1-1 mM) in Tris-HCl buffer (pH 8.0) at 25degC. The formation of cis,cis-muconic acid is monitored by UV absorbance at 260 nm (ε = 16,800 M-¹cm-¹).
|
| Cell Assay |
For cell studies, cis,cis-muconic acid is added to culture medium of bacterial strains (e.g., Pseudomonas putida) engineered for aromatic compound degradation at 1-10 mM. It serves as a carbon source, and bacterial growth is monitored by OD600. It can also be used as an internal standard in metabolomics.
|
| Animal Protocol |
No animal studies are performed with this compound as a pharmacological agent. In toxicology studies, rodents are exposed to benzene by inhalation or gavage, and urinary cis,cis-muconic acid is measured by LC-MS or GC-MS as a biomarker of benzene exposure.
|
| ADME/Pharmacokinetics |
The compound is a small polar dicarboxylic acid (MW 142.11) with good water solubility. In humans, it is renally cleared after conjugation with glycine. Its plasma half-life is short (1-2 hours). It is stable in urine at -20degC for weeks.
|
| Toxicity/Toxicokinetics |
Cis,cis-muconic acid has low toxicity; it is a normal microbial metabolite. The oral LD50 in rats is >2000 mg/kg. No significant genotoxicity or carcinogenicity is reported. It is considered safe as a chemical intermediate and analytical standard.
|
| References |
|
| Additional Infomation |
cis-cis-mucoconic acid is the cis-cis isomer of mucoconic acid. It is produced by the degradation of chlorobenzene by bacteria such as Bacillus and is a bacterial xenobiotic metabolite. It is the conjugate acid of (2Z,4Z)-5-carboxypent-2,4-dienoic acid. Cis-cis-mucoconic acid has been reported in both Rhodococcus and Plascotides simplex, and relevant data are available. See also: cis-cis-mucoconic acid (note moved to).
Cis,cis-muconic acid is used as a platform chemical for the production of adipic acid (a precursor to nylon-6,6) via hydrogenation. It is also a standard in HPLC analysis and a biomarker for benzene exposure in human biomonitoring. It is a key intermediate in microbial degradation of aromatic pollutants. Store at room temperature. |
| Molecular Formula |
C6H6O4
|
|---|---|
| Molecular Weight |
142.11
|
| Exact Mass |
142.026
|
| CAS # |
1119-72-8
|
| PubChem CID |
5280518
|
| Appearance |
White to light yellow solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
345.4±15.0 °C at 760 mmHg
|
| Melting Point |
194-195ºC(lit.)
|
| Flash Point |
176.9±16.9 °C
|
| Vapour Pressure |
0.0±1.6 mmHg at 25°C
|
| Index of Refraction |
1.549
|
| LogP |
-0.21
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
10
|
| Complexity |
168
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C(=C\C(=O)O)\C=C/C(=O)O
|
| InChi Key |
TXXHDPDFNKHHGW-CCAGOZQPSA-N
|
| InChi Code |
InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1-,4-2-
|
| Chemical Name |
(2Z,4Z)-hexa-2,4-dienedioic acid
|
| 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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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) |
DMSO :~250 mg/mL (~1759.20 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (14.64 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (14.64 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (14.64 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.0368 mL | 35.1840 mL | 70.3680 mL | |
| 5 mM | 1.4074 mL | 7.0368 mL | 14.0736 mL | |
| 10 mM | 0.7037 mL | 3.5184 mL | 7.0368 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.
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