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| Other Sizes |
| Targets |
As an endogenous metabolite, NSC 8751 does not have a specific therapeutic target in the traditional sense. However, it is known to be converted to beta-hydroxybutyryl-CoA by the enzyme known as crotonase (enoyl CoA hydratase) present in the liver and other tissues. It has been demonstrated to inhibit the formation of infectious diseases by binding to the agonist binding site on the surface of bacteria. It is also used as a reference compound for evaluating the skin sensitization and toxicological safety of structurally similar unsaturated carboxylic acid fragrances.
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| ln Vitro |
NSC 8751 is primarily used in vitro to evaluate the skin sensitization and toxicological safety of structurally similar unsaturated carboxylic acid fragrances (such as 2-methyl-trans-2-butenoic acid). For example, the human repeated patch test (HRIPT) and local lymph node assay can be used to confirm the safety of similar substances in cosmetics. The toxicological data of NSC 8751 can be used to deduce the safety of similar compounds through cross-species and structural analogies. It has been shown that when NSC 8751 is applied to local lymph nodes, a 50% concentration does not cause skin sensitization, and its structural analogs have been shown to be non-genotoxic.
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| ln Vivo |
In vivo activity data for NSC 8751 as a standalone therapeutic compound are not extensively reported, as it is primarily utilized as a reference standard for toxicological evaluation rather than as a therapeutic agent. The compound is used in animal models to assess the safety and toxicological properties of structurally similar fragrance ingredients. Its in vivo effects are primarily related to its metabolism via the enzyme crotonase to beta-hydroxybutyryl-CoA. The compound's safety profile in vivo is established through standard toxicological assessments such as the local lymph node assay.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for NSC 8751 typically involve studying its interaction with crotonase (enoyl CoA hydratase), the enzyme responsible for its conversion to beta-hydroxybutyryl-CoA. Enzyme activity assays can be performed to measure the rate of conversion of crotonic acid to beta-hydroxybutyryl-CoA. Additionally, binding studies may be conducted to assess the interaction of crotonic acid with bacterial surface proteins, as it has been shown to inhibit the formation of infectious diseases by binding to the agonist binding site on the surface of bacteria.
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| Cell Assay |
In vitro cell-based assays for NSC 8751 typically involve the use of cell lines to evaluate its cytotoxic or sensitizing potential. The human repeated patch test (HRIPT) is a standard assay used to confirm the safety of similar substances in cosmetics. Additionally, cell-based assays may be used to evaluate the compound's effects on bacterial growth, given its demonstrated ability to inhibit the formation of infectious diseases. The compound is also used as a reference standard in metabolic studies to assess the activity of crotonase in various cell types.
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| Animal Protocol |
In vivo animal studies for NSC 8751 typically involve the use of animal models to assess its toxicological and sensitizing potential. The local lymph node assay (LLNA) is a standard in vivo assay used to evaluate the skin sensitization potential of chemicals. In this assay, the compound is applied to the ears of mice, and the proliferation of lymphocytes in the draining lymph nodes is measured. The compound has been shown to not cause skin sensitization at a 50% concentration in this assay. These studies are critical for the safety assessment of fragrance ingredients.
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| ADME/Pharmacokinetics |
Metabolism/Metabolites...It is known that crotonic acid is converted to β-hydroxybutyryl-CoA by crotonic acid hydrate, which is present in the liver and other tissues.
NSC 8751 has a molecular formula of C4H6O2 and a molecular weight of 86.09. The compound appears as a white to off-white solid powder. It has a density of 1.027, a boiling point of 185-199 ºC, a melting point of 70-73ºC, and a flash point of 88 ºC. The logP is 0.8, and it is soluble in water. The compound is stable at room temperature for up to 3 years and should be stored as a powder at -20°C for up to 3 years or at 4°C for up to 2 years. |
| Toxicity/Toxicokinetics |
The toxicity profile of NSC 8751 has been evaluated as part of its use in safety assessment of fragrance ingredients. When applied to local lymph nodes, a 50% concentration does not cause skin sensitization. Structural analogs of NSC 8751 have been shown to be non-genotoxic. The compound is corrosive to metals and tissue. It is considered an endogenous metabolite and is used as a reference compound for evaluating the safety of structurally similar unsaturated carboxylic acid fragrances.
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| Additional Infomation |
Crotonic acid is a white crystalline solid, transported in solid or liquid form. It is soluble in water but less dense. It is corrosive to metals and tissues. Crotonic acid is a butyric acid with a trans double bond at the C-2 position. It has been isolated from carrot (Daucus carota). It is a plant metabolite and the conjugate acid of crotonic acid. Crotonic acid has been reported in croton (Croton tiglium), carrot (Daucus carota), and other organisms with relevant data. See also: crotonic acid (note moved to); isocrotonic acid (note moved to).
NSC 8751 ((E)-2-Butenoic acid; (E)-Crotonic acid; trans-2-Butenoic acid; trans-Crotonic acid) (CAS 107-93-7) has a molecular formula of C4H6O2 and a molecular weight of 86.09. It is an endogenous metabolite and an unsaturated carboxylic acid compound. The compound is a but-2-enoic acid with a trans-double bond at C-2 and has been isolated from Daucus carota. It is primarily used as a reference standard for evaluating the safety of fragrance ingredients and structurally similar compounds. It has a role as a plant metabolite and is not approved for therapeutic use. |
| Molecular Formula |
C4H6O2
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|---|---|
| Molecular Weight |
86.09
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| Exact Mass |
86.036
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| CAS # |
107-93-7
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| Related CAS # |
NSC 8751-d6;21386-86-7
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| PubChem CID |
637090
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| Appearance |
White to off-white solid powder
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| Density |
1.027
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| Boiling Point |
185-199 ºC
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| Melting Point |
70-73ºC
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| Flash Point |
88 ºC
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| Vapour Pressure |
0.5±0.7 mmHg at 25°C
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| Index of Refraction |
1.449
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| LogP |
0.8
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
6
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| Complexity |
73.6
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C/C=C/C(=O)O
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| InChi Key |
LDHQCZJRKDOVOX-NSCUHMNNSA-N
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| InChi Code |
InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+
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| Chemical Name |
(E)-but-2-enoic acid
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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) |
H2O :~33.33 mg/mL (~387.15 mM)
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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 | 11.6158 mL | 58.0788 mL | 116.1575 mL | |
| 5 mM | 2.3232 mL | 11.6158 mL | 23.2315 mL | |
| 10 mM | 1.1616 mL | 5.8079 mL | 11.6158 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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