| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
The primary target of Benzoyl-CoA is glycine N-acyltransferase (GLYAT). This enzyme specifically catalyzes the transfer of the benzoyl group from Benzoyl-CoA to glycine, forming hippurate, which is the major detoxification pathway for benzoate in mammals. In microorganisms, it acts by inducing conformational changes in MarR family transcriptional regulators (e.g., GenR), relieving the repression of downstream genes and initiating the expression of degradation pathways. It is also a substrate for benzoyl-CoA thioesterase.
|
|---|---|
| ln Vitro |
In cell-free systems, Benzoyl-CoA serves as an acyl donor for assaying glycine N-acyltransferase (GLYAT) activity, with studies showing that GLYAT has a higher affinity for Benzoyl-CoA compared to phenylacetyl-CoA. In rat liver mitochondrial extracts, p-hydroxybenzoyl-CoA (a derivative of Benzoyl-CoA) is involved in ubiquinone-9 biosynthesis, exhibiting an apparent Km of 5 × 10⁻⁵ M. Additionally, in microbial enzymatic studies, recombinant benzoyl-CoA thioesterase specifically hydrolyzes Benzoyl-CoA, showing the highest activity with mono-substituted derivatives such as 4-hydroxybenzoyl-CoA.
|
| ln Vivo |
There is limited direct in vivo data available regarding the activity of administered Benzoyl coenzyme A. Existing in vivo evidence primarily comes from metabolic regulation studies: in Comamonas testosteroni, Benzoyl-CoA acts as a metabolic intermediate of the benzoate degradation pathway and serves as an effector molecule that binds to the regulatory protein GenR, thereby inducing the expression of genes related to the gentisate pathway. In mammals, its primary role is as an intermediate in the rapid conversion of ingested benzoate to hippurate in the liver and kidney for urinary excretion.
|
| Enzyme Assay |
Benzoyl-CoA can be used as a substrate for acyltransferase activity assays in cell-free systems. A typical protocol involves incubating purified glycine N-acyltransferase (GLYAT), Benzoyl-CoA, and the substrate glycine in a Tris-HCl buffer (pH 8.0). After incubation at 37°C, enzyme activity is quantified by measuring the formation of hippurate using HPLC or by detecting the released free CoA-SH using DTNB.
|
| Cell Assay |
In cellular assays, Benzoyl-CoA is used to study xenobiotic metabolism or mitochondrial function. Due to its high polarity and membrane impermeability, it is typically administered using permeabilized cells (e.g., digitonin-treated) or via microinjection. For example, in isolated rat hepatocytes suspended in Krebs-Henseleit buffer, sodium benzoate is added (to generate Benzoyl-CoA intracellularly via natural conversion) or Benzoyl-CoA is added directly after permeabilization to measure hippurate synthesis rates and changes in mitochondrial respiratory function.
|
| Animal Protocol |
Benzoyl-CoA is typically not administered directly to animals but is generated endogenously by administering sodium benzoate orally or intraperitoneally. In typical pharmacokinetic studies, rats are given benzoic acid via gavage, and blood and urine samples are collected at various time points (0-24 hours). LC-MS/MS is used to detect benzoic acid, glycine conjugates (hippurate), and metabolic intermediates in plasma to infer the in vivo generation and turnover of Benzoyl-CoA.
|
| ADME/Pharmacokinetics |
Specific pharmacokinetic data (e.g., half-life, volume of distribution) for Benzoyl-CoA is extremely limited in public literature. As an intracellular metabolite, it is unstable in plasma and is rapidly hydrolyzed by esterases or metabolized. In vivo, it exists primarily as a transient intermediate; it is synthesized in the liver mitochondria and quickly utilized by glycine N-acyltransferase, with its rate of formation being rate-limiting for hippurate production. In vitro studies indicate that Benzoyl-CoA is susceptible to hydrolysis under neutral and alkaline conditions, with a half-life of tens of minutes at 30°C under alkaline conditions.
|
| Toxicity/Toxicokinetics |
Benzoyl coenzyme A itself is an endogenous metabolite and is non-toxic at normal physiological concentrations. However, its precursor, sodium benzoate, can cause glycine depletion in the liver at high doses, leading to central nervous system toxicity. No specific toxicological data is available for Benzoyl-CoA alone. When used as a chemical reagent, standard laboratory practices should be followed to avoid inhalation, ingestion, and skin contact. In microorganisms, abnormal accumulation of Benzoyl-CoA can lead to CoA pool depletion by inhibiting thioesterase activity, thereby affecting cellular metabolism.
|
| References |
| Molecular Formula |
C28H40N7O17P3S
|
|---|---|
| Molecular Weight |
871.64
|
| Exact Mass |
871.141
|
| CAS # |
6756-74-7
|
| Related CAS # |
102185-37-5
|
| PubChem CID |
9543169
|
| Appearance |
Typically exists as solids at room temperature
|
| LogP |
1.342
|
| Hydrogen Bond Donor Count |
9
|
| Hydrogen Bond Acceptor Count |
22
|
| Rotatable Bond Count |
21
|
| Heavy Atom Count |
56
|
| Complexity |
1510
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)C(C(=O)NCCC(=O)NCCSC(=O)C4=CC=CC=C4)O
|
| InChi Key |
VEVJTUNLALKRNO-TYHXJLICSA-N
|
| 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)/t17-,20-,21-,22+,26-/m1/s1
|
| Chemical Name |
S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] benzenecarbothioate
|
| Synonyms |
Benzoyl-coa; Benzoyl Coenzyme A; Coenzyme A, S-benzoate; Benzoyl CoA
|
| 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 | 1.1473 mL | 5.7363 mL | 11.4726 mL | |
| 5 mM | 0.2295 mL | 1.1473 mL | 2.2945 mL | |
| 10 mM | 0.1147 mL | 0.5736 mL | 1.1473 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
