| Size | Price | Stock | Qty |
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Purity: =99.17%
| Targets |
Natural product; adiponectin, peroxisome proliferator-activated receptor γ2 (PPARγ2), glucose transporter 4 (GLUT4), fatty acid-binding protein (aP2), and CCAAT/enhancer-binding protein (C/EBP) α and β
The specific molecular targets of Retrofractamide A are not fully characterized. However, it is known to promote adipogenesis in 3T3-L1 cells, indicating that it modulates pathways involved in the differentiation of preadipocytes into mature adipocytes. This suggests interactions with key transcriptional regulators of adipocyte differentiation such as PPARγ and C/EBPα. |
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| ln Vitro |
In a previous study, retrofractamide A from the fruit of Piper chaba was shown to promote adipogenesis in 3T3-L1 cells. In the present study, retrofractamide A and its derivatives were synthesized, and their adipogenetic effects in 3T3-L1 cells were examined. Among the tested compounds, an amide composed of 9-(3',4'-methylenedioxyphenyl)-nona-2E,4E,8E-trienoic acid and an n-butyl or n-pentyl amine showed strongest activity. Moreover, the amide with the n-pentyl amine moiety significantly increased the uptake of 2-deoxyglucose into the cells, and also increased the mRNA levels of adiponectin, peroxisome proliferator-activated receptor γ2 (PPARγ2), glucose transporter 4 (GLUT4), fatty acid-binding protein (aP2), and CCAAT/enhancer-binding protein (C/EBP) α and β in a similar manner as the PPARγ agonist troglitazone, although it had less agonistic activity against PPARγ.[1]
In vitro, Retrofractamide A promotes adipogenesis in 3T3-L1 cells, a well-established model for studying fat cell differentiation. This activity suggests that the compound can stimulate the differentiation of preadipocytes into mature adipocytes, a process characterized by the accumulation of lipid droplets and the expression of adipocyte-specific genes. Specific EC50 or IC50 values are not detailed in the available literature. |
| ln Vivo |
Specific in vivo data for Retrofractamide A are not reported in the available literature. Given its in vitro activity in promoting adipogenesis, the compound has potential for in vivo studies in models of obesity, metabolism, and fat tissue development. However, specific published in vivo protocols for this compound are not available.
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| Enzyme Assay |
The adipogenic activity of Retrofractamide A is assessed using cell-based differentiation assays. 3T3-L1 preadipocytes are cultured and induced to differentiate into adipocytes using a standard differentiation cocktail. Retrofractamide A is added to the culture medium during the differentiation process. Adipogenesis is quantified by Oil Red O staining of accumulated lipid droplets, which is measured spectrophotometrically, or by measuring the activity of glycerol-3-phosphate dehydrogenase (GPDH), a marker of adipocyte differentiation.
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| Cell Assay |
For cellular studies, 3T3-L1 preadipocytes are cultured in Dulbecco's Modified Eagle Medium (DMEM) supplemented with 10% fetal bovine serum (FBS). Cells are treated with Retrofractamide A at various concentrations during the differentiation process. Adipogenesis is assessed by Oil Red O staining, triglyceride content measurement, and qPCR or Western blot analysis of adipogenic marker genes such as PPARγ, C/EBPα, and aP2. The compound is typically dissolved in DMSO and diluted in culture media.
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| Animal Protocol |
In vivo studies for Retrofractamide A would be conducted in appropriate animal models of adipogenesis and metabolism. For example, mice could be treated with the compound via oral gavage or intraperitoneal injection, and effects on adipose tissue development, body weight, and metabolic parameters could be assessed. However, specific published protocols for this compound are not available.
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| ADME/Pharmacokinetics |
Specific pharmacokinetic data for Retrofractamide A are not reported. The compound has a molecular formula of C20H25NO3 and a molecular weight of 327.42 g/mol. As an amide, it may have moderate lipophilicity. Pharmacokinetic studies would be required to determine its absorption, distribution, metabolism, and excretion profile.
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| Toxicity/Toxicokinetics |
Specific toxicological data for Retrofractamide A are not reported. As a natural product from Piper chaba, which has traditional medicinal uses, the compound is generally considered to have a moderate safety profile. However, comprehensive toxicology studies have not been published. The compound is for research use only and not for human therapeutic use.
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| References | |
| Additional Infomation |
Retrofractamide A belongs to the benzodioxane class of compounds. It has been reported to be found in Piper mullesua, Piper eucalyptifolium, and other organisms with relevant data.
Retrofractamide A is an amide constituent from Piper chaba fruit that promotes adipogenesis in 3T3-L1 cells. Molecular formula: C20H25NO3, molecular weight: 327.42 g/mol. No clinical trials exist. For research use only. |
| Molecular Formula |
C20H25NO3
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|---|---|
| Molecular Weight |
327.42
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| Exact Mass |
327.183
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| CAS # |
94079-67-1
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| PubChem CID |
11012859
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| Appearance |
Typically exists as solid at room temperature
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| Melting Point |
129 °C
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| LogP |
4.484
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
24
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| Complexity |
468
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)CNC(=O)C=CC=CCCC=CC1=CC2=C(C=C1)OCO2
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| InChi Key |
BPSWISYORIWKCT-FCGWLDPVSA-N
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| InChi Code |
InChI=1S/C20H25NO3/c1-16(2)14-21-20(22)10-8-6-4-3-5-7-9-17-11-12-18-19(13-17)24-15-23-18/h4,6-13,16H,3,5,14-15H2,1-2H3,(H,21,22)/b6-4+,9-7+,10-8+
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| Chemical Name |
(2E,4E,8E)-9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,4,8-trienamide
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| Synonyms |
RETROFRACTAMIDE A; 94079-67-1; (2E,4E,8E)-9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,4,8-trienamide; (2E,4E,8E)-9-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,4,8-trienamide; VVK45GJ3K5;
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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 | 3.0542 mL | 15.2709 mL | 30.5418 mL | |
| 5 mM | 0.6108 mL | 3.0542 mL | 6.1084 mL | |
| 10 mM | 0.3054 mL | 1.5271 mL | 3.0542 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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