| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| Other Sizes |
| Targets |
Microbial Metabolite; The biological effects of benzoyl CoA are primarily mediated through its role as a substrate for various enzymes. Its main targets include: (1) Glycine N-acyltransferase (GLYAT, EC 2.3.1.13) : A mitochondrial acyltransferase that catalyzes the conjugation of benzoyl CoA with glycine to form hippuric acid (benzoylglycine), a key step in benzoate detoxification in mammals. This enzyme shows a preference for benzoyl CoA; (2) Benzoyl-CoA reductase : Found in anaerobic bacteria, it catalyzes the reductive dearomatization of benzoyl CoA to cyclohex-1,5-diene-1-carboxyl-CoA, a key step in the anaerobic ring cleavage of aromatic compounds; (3) Benzoyl-CoA thioesterase : Hydrolyzes benzoyl CoA to free benzoate and CoA, regulating the intracellular CoA pool balance.
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| ln Vitro |
In vitro, benzoyl CoA primarily serves as a substrate for enzymatic reactions to measure the activity of relevant enzymes. Studies show that recombinant benzoyl-CoA thioesterase from Azoarcus evansii efficiently hydrolyzes benzoyl CoA, with a specific activity of approximately 20 nmol·min⁻¹·mg⁻¹ protein. This enzyme also exhibits higher activity towards mono-substituted benzoyl CoA derivatives (such as 4-hydroxybenzoyl CoA) but shows no activity towards aliphatic CoA thioesters. Furthermore, when benzoyl CoA acts as a substrate for glycine N-acyltransferase (GLYAT), its Michaelis constant (Km) indicates a high affinity for the enzyme, with lipoic acid competitively inhibiting the enzyme's binding to benzoyl CoA with an IC50 of approximately 0.3 mM.
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| ln Vivo |
In vivo, as a metabolic intermediate, the activity of benzoyl CoA is primarily reflected in its involvement in xenobiotic detoxification and endogenous metabolic pathways. In mammals, benzoic acid is activated to benzoyl CoA in liver mitochondria by benzoyl-CoA synthetase, which is then conjugated with glycine by glycine N-acyltransferase (GLYAT) to form hippuric acid (benzoylglycine) for urinary excretion. In the anaerobic phototrophic bacterium Rhodopseudomonas palustris, exogenous benzoate is efficiently taken up and rapidly converted to benzoyl CoA, which is then further reductively metabolized. In rat liver mitochondria, p-hydroxybenzoyl CoA serves as an intermediate in the ubiquinone (Coenzyme Q) biosynthesis pathway, participating in the synthesis of 2-nonaprenyl-6-methoxyphenol (2-NPMP).
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| Enzyme Assay |
Spectrophotometry or High-Performance Liquid Chromatography (HPLC) is commonly used for in vitro enzyme activity assays involving benzoyl CoA. For glycine N-acyltransferase (GLYAT) activity measurement: The reaction system contains 100 mM Tris-HCl buffer (pH 8.0-8.5), 50 mM KCl, 10 mM MgCl₂, 2 mM ATP, 0.5 mM CoA, 10 mM potassium benzoate (substrate), 50 mM glycine (acyl acceptor), and an appropriate amount of enzyme (e.g., mitochondrial extract or purified GLYAT). Incubate at 37°C for 10-30 minutes, stop the reaction with 10% trichloroacetic acid, and centrifuge to remove protein. The product hippuric acid in the supernatant is quantified by HPLC-UV (230 nm). Lipoic acid (LA) can serve as a positive control inhibitor, significantly inhibiting GLYAT activity at concentrations of 0.3-1.5 mM.
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| Cell Assay |
To study benzoyl CoA metabolism at the cellular level, hepatocytes or primary hepatocytes are commonly used. For a study on the accumulation of p-alkyl-benzoyl CoA conjugates: Rat hepatocytes are plated in culture plates and incubated overnight at 37°C in 5% CO₂. Add culture medium containing p-alkyl-phenylpropanals (e.g., p-tert-butylphenylpropanal, 100 μM) or benzoic acid derivatives and incubate for 4-24 hours. Collect cells at different time points, wash with PBS, add extraction solution containing methanol/acetonitrile to lyse the cells, and centrifuge to obtain the supernatant. Detect the accumulation levels of p-alkyl-benzoyl CoA conjugates in cell extracts using high-resolution liquid chromatography-mass spectrometry (LC-HRMS). Studies have found that compounds causing male reproductive toxicity lead to sustained high accumulation of the benzoyl CoA thioester in cells.
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| Animal Protocol |
In vivo animal experiments typically use rat models to study benzoate metabolism and detoxification. A classic protocol involves: selecting male Sprague-Dawley rats (200-300 g), administering benzoic acid (1 mmol/kg body weight) or a benzoyl CoA precursor via intravenous injection after anesthesia. Set up a treatment group and a control group (saline). Collect blood samples at multiple time points (e.g., 0, 15, 30, 60, 120 minutes) before and after administration, and also collect urine (e.g., using metabolic cages). Centrifuge blood to obtain serum and analyze hippuric acid concentration by HPLC. The urinary excretion of hippuric acid can serve as an indicator of benzoyl CoA metabolic activity. Studies have shown that lipoic acid (LA, 0.5-1.5 mmol/kg, intraperitoneal injection) dose-dependently inhibits the conversion of benzoic acid to hippuric acid, reducing the clearance rate of benzoic acid from the blood.
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| ADME/Pharmacokinetics |
No direct systematic reports on the pharmacokinetic parameters of benzoyl CoA itself are available in the public literature. As a highly polar acyl-CoA thioester, this compound has low membrane permeability and primarily functions within cells (especially mitochondria). As a metabolic intermediate in vivo, its "half-life" is extremely short, determined by the activity of relevant metabolic enzymes—it is rapidly utilized or hydrolyzed by downstream enzymes after synthesis. Studies indicate that benzoyl CoA thioester is unstable under alkaline conditions (pH > 9) and prone to hydrolysis, with a half-life of approximately 20 minutes. At the cellular level, p-alkyl-benzoyl CoA conjugates produced from the metabolism of certain xenobiotics can accumulate in hepatocytes for several hours, suggesting that their clearance may depend on specific hydrolase systems.
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| Toxicity/Toxicokinetics |
Benzoyl CoA itself is an endogenous metabolic intermediate and does not exhibit significant toxicity at physiological concentrations. However, its abnormal accumulation may be associated with specific toxic effects. Studies indicate that certain aromatic aldehydes (e.g., p-tert-butylphenylpropanal) are metabolized to p-alkyl-benzoic acids and then to p-alkyl-benzoyl CoA thioesters, which accumulate to high and sustained levels in testicular cells. This accumulation is thought to interfere with CoA-dependent spermatogenesis, leading to male reproductive toxicity in rats (oral dose ≥ 25 mg/kg·day). This finding led researchers to design novel fragrance compounds that do not form benzoyl CoA thioesters, successfully eliminating the reproductive toxicity. Furthermore, lipoic acid can interfere with hippuric acid formation by inhibiting benzoyl-CoA synthetase and GLYAT (IC50 of 1.5 mM and 0.3 mM, respectively) and depleting hepatic CoA. According to supplier information, this compound is strictly for research use only and is not intended for human use.
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| References | |
| Additional Infomation |
Benzoyl-CoA is the simplest member of the benzoyl-CoA class. It is a product of the condensation of the sulfhydryl group of coenzyme A with the carboxyl group of benzoic acid. It is a mouse metabolite, functionally related to benzoic acid, and is the conjugate acid of benzoyl-CoA(4-). Benzoyl-CoA has been reported to be detected in marine Streptomyces, and relevant data are available for reference.
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| Molecular Formula |
C28H37LI3N7O17P3S
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|---|---|
| Molecular Weight |
889.44
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| Exact Mass |
877.15
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| CAS # |
102185-37-5
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| Related CAS # |
6756-74-7
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| PubChem CID |
9543169
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| Appearance |
White to off-white solid powder
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| LogP |
1.779
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| Hydrogen Bond Donor Count |
9
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| Hydrogen Bond Acceptor Count |
22
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| Rotatable Bond Count |
21
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| Heavy Atom Count |
56
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| Complexity |
1510
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| Defined Atom Stereocenter Count |
5
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| SMILES |
CC(C)(COP(=O)([O-])OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)([O-])[O-])[C@H](C(=O)NCCC(=O)NCCSC(=O)C4=CC=CC=C4)O
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| InChi Key |
VEVJTUNLALKRNO-TYHXJLICSA-J
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| InChi Code |
InChI=1S/C28H40N7O17P3S/c1-28(2,22(38)25(39)31-9-8-18(36)30-10-11-56-27(40)16-6-4-3-5-7-16)13-49-55(46,47)52-54(44,45)48-12-17-21(51-53(41,42)43)20(37)26(50-17)35-15-34-19-23(29)32-14-33-24(19)35/h3-7,14-15,17,20-22,26,37-38H,8-13H2,1-2H3,(H,30,36)(H,31,39)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/p-4/t17-,20-,21-,22+,26-/m1/s1
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| Chemical Name |
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[[[[(3R)-4-[[3-(2-benzoylsulfanylethylamino)-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl] phosphate
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| Synonyms |
Benzoyl-coa; Benzoyl Coenzyme A; Benzoyl CoA; Coenzyme A, S-benzoate;
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| HS Tariff Code |
2934.99.9001
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| 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)
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| 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
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|---|---|
| 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 | 1.1243 mL | 5.6215 mL | 11.2430 mL | |
| 5 mM | 0.2249 mL | 1.1243 mL | 2.2486 mL | |
| 10 mM | 0.1124 mL | 0.5622 mL | 1.1243 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
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