| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
Not applicable. N-Acetyl-S-(3,4-dihydroxybutyl)-L-cysteine is a detoxification metabolite and does not have a specific biological target for therapeutic purposes. It is formed through the mercapturic acid pathway, which is a phase II detoxification mechanism to eliminate reactive epoxides. It is an inert end product excreted in urine. Its primary value is as a biomarker of internal dose for 1,3-butadiene exposure. It does not bind to any receptor or enzyme for pharmacological benefit. It is an analytical standard for environmental and occupational health research.
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| ln Vitro |
In vitro, this compound is not used for biological activity studies. It is an analytical standard for LC-MS and HPLC methods used in biomonitoring. For method development, it is dissolved in water or methanol (1 mg/mL) to prepare calibration curves ranging from 0.1-100 ng/mL in blank urine. It is used to assess the specificity, linearity, and accuracy of assays designed to measure mercapturic acids. It does not possess inherent cytotoxicity or enzymatic activity. It may be used as a positive control in assays for glutathione-S-transferase activity.
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| ln Vivo |
In vivo, N-Acetyl-S-(3,4-dihydroxybutyl)-L-cysteine is not administered as a drug. It is an endogenous metabolite formed after exposure to 1,3-butadiene. In research, its concentration is measured in urine samples from animal models (e.g., rats or mice) exposed to butadiene to validate the relationship between external exposure dose and internal biomarker levels. It is used to assess the efficiency of glutathione conjugation pathways. It is not used in efficacy studies (e.g., treating cancer).
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| Enzyme Assay |
General protocol for in vitro analytical use: For LC-MS/MS analysis, prepare a 1 mg/mL stock solution in methanol. Prepare calibration standards in blank human urine at 0.1, 0.5, 1, 5, 10, 25, 50, and 100 ng/mL. Add an internal standard (e.g., N-Acetyl-S-(3,4-dihydroxybutyl)-L-cysteine-d3 or 13C-labeled analog, 10 ng/mL) to each standard and sample. For sample preparation, centrifuge urine, filter through a 0.22 um membrane, and inject 5-10 uL onto an LC-MS/MS system. Use a HILIC column (2.1 × 100 mm, 1.7 um) with mobile phase of acetonitrile:water (80:20) containing 0.1% formic acid. MS detection in positive ion mode: parent m/z 252 → product ion m/z 134. Construct a calibration curve by plotting peak area ratio vs. concentration. Store the standard at -20degC.
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| Cell Assay |
General protocol for in vitro cell-based experiments: Not applicable for biological activity. For a metabolism study, incubate 1,3-butadiene epoxide with glutathione (5 mM) and glutathione S-transferase (0.1 U) in PBS (pH 7.4) at 37degC for 1-2 h. Add N-acetyltransferase and acetyl-CoA to convert the glutathione conjugate to the mercapturic acid. Analyze the reaction mixture by LC-MS. The compound DHBMA will be detected as the final product. No direct cell culture is required.
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| Animal Protocol |
General protocol for in vivo animal experiments: For a biomarker validation study, expose male Sprague-Dawley rats to 1,3-butadiene (200 ppm, inhalation) for 6 hours. Collect 24-hour urine post-exposure. Add internal standard to 1 mL urine, centrifuge, and analyze by LC-MS/MS as described. Quantify DHBMA levels to assess internal dose. This is a toxicokinetic study, not a drug efficacy model.
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| ADME/Pharmacokinetics |
General pharmacokinetic properties: N-Acetyl-S-(3,4-dihydroxybutyl)-L-cysteine (MW 251.30) is a polar, water-soluble mercapturic acid. It is not a drug, so comprehensive ADME data are not available. As a metabolite, it is formed in the liver and rapidly excreted in urine. The elimination half-life in humans is short (approximately 6-12 hours). It is not protein-bound. For storage, the solid reference standard is stable at -20degC for up to 3 years. Stock solutions in water or methanol can be stored at -80degC for 6 months. Protect from light.
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| Toxicity/Toxicokinetics |
General toxicity profile: DHBMA is a detoxification product and is not considered acutely toxic. It is an endogenous metabolite, and at the low levels measured in urine (ng/mL range), it poses no hazard. As a chemical standard, it is an irritant. Standard laboratory safety precautions (gloves, lab coat, safety glasses) should be used. Avoid inhalation of dust. It is not a controlled substance. For research use only.
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| References |
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| Additional Infomation |
N-Acetyl-S-(3,4-dihydroxybutyl)-L-cysteine is also known as DHBMA, 4-(N-Acetyl-L-cystein-S-yl)-1,2-dihydroxybutane, or N-Acetyl-S-(3,4-dihydroxybutyl)-L-cysteine (mixture of diastereomers). It is the major urinary mercapturic acid metabolite of 1,3-butadiene. The compound is often used as a human biomonitoring standard in studies investigating the health effects of smoking (cigarette smoke contains butadiene) and occupational exposure in the rubber and plastics industries. For research and forensic use only.
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| Molecular Formula |
C9H17NO5S
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|---|---|
| Molecular Weight |
251.30
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| Exact Mass |
251.083
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| CAS # |
144889-50-9
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| Related CAS # |
N-Acetyl-S-(3,4-dihydroxybutyl)-L-cysteine-d7; 1240398-27-9
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| PubChem CID |
44151464
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| Appearance |
Typically exists as solids at room temperature
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| Hydrogen Bond Donor Count |
4
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
16
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| Complexity |
236
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC(=O)N[C@@H](CSCCC(CO)O)C(=O)O
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| InChi Key |
VGJNEDFZFZCLSX-MQWKRIRWSA-N
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| InChi Code |
InChI=1S/C9H17NO5S/c1-6(12)10-8(9(14)15)5-16-3-2-7(13)4-11/h7-8,11,13H,2-5H2,1H3,(H,10,12)(H,14,15)/t7?,8-/m0/s1
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| Chemical Name |
(2R)-2-acetamido-3-(3,4-dihydroxybutylsulfanyl)propanoic acid
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| Synonyms |
Dihydroxybutyl mercapturic acid; DHBMA
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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 | 3.9793 mL | 19.8965 mL | 39.7931 mL | |
| 5 mM | 0.7959 mL | 3.9793 mL | 7.9586 mL | |
| 10 mM | 0.3979 mL | 1.9897 mL | 3.9793 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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