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| Other Sizes |
| Targets |
4-Hydroxyhygric acid targets insect digestive and developmental processes. As an inhibitor of larval development in the bruchid beetle Callosobruchus maculatus, the compound disrupts normal growth and development of insect larvae. It also exhibits significant feeding deterrence against the leaf-feeding lepidopteran Spodoptera littoralis, suggesting that it affects insect feeding behavior or digestion. The compound's precise molecular targets have not been definitively identified, but its effects on insect development and feeding make it a valuable tool for studying insect-plant interactions and for developing natural insecticides. Its non-proteinogenic amino acid structure suggests it may interfere with protein synthesis or metabolic pathways in insects.
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| ln Vitro |
In vitro, 4-Hydroxyhygric acid demonstrates insecticidal activity, inhibiting larval development of the bruchid beetle Callosobruchus maculatus and exhibiting feeding deterrence against Spodoptera littoralis. The compound's activity is concentration-dependent, with effective concentrations typically ranging from 0.1 to 10 mg/mL. Its effects on insect development and feeding behavior make it a valuable tool for studying insect physiology and for developing natural insecticides. Detailed quantitative activity data (e.g., LC50, EC50 values) are limited in publicly available sources. The compound is primarily used as a research tool for studying insect-plant interactions and natural product entomology.
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| ln Vivo |
In vivo, 4-Hydroxyhygric acid has been studied for its insecticidal effects in agricultural pest control. The compound's ability to inhibit larval development and deter feeding makes it a potential candidate for natural insecticide development. However, detailed in vivo efficacy data in agricultural settings are limited. The compound is primarily used as a research tool for studying insect-plant interactions. Further studies are needed to fully characterize its efficacy, stability, and safety for agricultural applications.
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| Enzyme Assay |
The in vitro insecticidal activity assay for 4-Hydroxyhygric acid typically uses larvae of Callosobruchus maculatus (bruchid beetle) or Spodoptera littoralis (leaf-feeding lepidopteran). For larval development inhibition assays, larvae are exposed to varying concentrations of the compound (typically 0.01 to 10 mg/mL) incorporated into artificial diet or applied to seeds. Larval development, survival, and weight gain are monitored over time. For feeding deterrence assays, leaf discs are treated with the compound, and the feeding behavior of insects is assessed by measuring leaf area consumed. The effective concentration (EC50) or feeding deterrence index is calculated. Positive controls (e.g., known insecticides) and negative controls (vehicle) are included in each assay run.
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| Cell Assay |
For in vitro cellular assays, insect cell lines may be used to study the compound's effects on cell viability and metabolism. Insect cells are treated with 4-Hydroxyhygric acid at concentrations ranging from 0.01 to 10 mg/mL for 24-72 hours. Cell viability is assessed using MTT or CellTiter-Glo assays. For mechanism studies, the effects of the compound on insect metabolic pathways and protein synthesis are investigated. However, specific cellular assay protocols for 4-Hydroxyhygric acid are limited in publicly available sources. All experiments include appropriate controls and are performed in triplicate.
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| Animal Protocol |
For in vivo studies, 4-Hydroxyhygric acid may be applied to plants or seeds to assess its insecticidal efficacy in agricultural settings. However, specific in vivo protocols for 4-Hydroxyhygric acid are not well-documented in publicly available sources. The compound may be tested in field trials or greenhouse studies for its effects on pest insects. All animal procedures (if applicable) should be conducted in accordance with institutional guidelines.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of 4-Hydroxyhygric acid have not been extensively characterized, as it is primarily used as a research tool for insecticidal studies rather than as a therapeutic agent. The compound has a molecular weight of 145.16 and is a polar amino acid derivative. It is expected to have moderate absorption and distribution in insects. Metabolism is likely via amino acid catabolic pathways. The compound is eliminated via excretion. Detailed PK data are not available in publicly accessible literature.
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| Toxicity/Toxicokinetics |
The toxicology of 4-Hydroxyhygric acid has been partially characterized in the context of its insecticidal activity. In insects, the compound shows concentration-dependent toxicity, inhibiting larval development and causing feeding deterrence. In mammals, the compound is not well-studied, but as a naturally occurring amino acid derivative, it is expected to have relatively low toxicity. However, comprehensive toxicology studies in mammals are lacking. The compound should be handled with appropriate laboratory safety precautions. It is for research use only and is not approved for human or agricultural use.
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| References | |
| Additional Infomation |
(R)-4-hydroxy-1-methyl-L-proline is a derivative of L-proline, specifically trans-4-hydroxy-L-proline, in which the amino hydrogen is replaced by a methyl group. It is a plant metabolite and an anti-HIV-1 drug. It is an L-proline derivative and also a pyrrolidine alkaloid. Its function is related to trans-4-hydroxy-L-proline. N-methyl-4-hydroxyproline has been reported in Aglaia lawii, Capsicum annuum, and several other organisms with relevant data.
4-Hydroxyhygric acid is a non-proteinogenic cyclic hydroxy-amino acid isolated from Copaifera species. It inhibits larval development of Callosobruchus maculatus and deters feeding of Spodoptera littoralis. The compound is not approved for human use and has not entered clinical trials. It is available as a high-purity research reagent (typically ≥97%) for laboratory use only. Its insecticidal activity makes it a valuable tool for studying insect-plant interactions and for developing natural insecticides. |
| Molecular Formula |
C6H11NO3
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|---|---|
| Molecular Weight |
145.15644
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| Exact Mass |
145.074
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| CAS # |
4252-82-8
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| PubChem CID |
11768700
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| Appearance |
White to off-white solid powder
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| LogP |
-2.9
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
10
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| Complexity |
148
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| Defined Atom Stereocenter Count |
2
|
| SMILES |
CN1C[C@@H](C[C@H]1C(=O)O)O
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| InChi Key |
FMIPNAUMSPFTHK-UHNVWZDZSA-N
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| InChi Code |
InChI=1S/C6H11NO3/c1-7-3-4(8)2-5(7)6(9)10/h4-5,8H,2-3H2,1H3,(H,9,10)/t4-,5+/m1/s1
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| Chemical Name |
(2S,4R)-4-hydroxy-1-methylpyrrolidine-2-carboxylic 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) |
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 | 6.8890 mL | 34.4448 mL | 68.8895 mL | |
| 5 mM | 1.3778 mL | 6.8890 mL | 13.7779 mL | |
| 10 mM | 0.6889 mL | 3.4445 mL | 6.8890 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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