| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
The primary targets of Genipin include uncoupling protein 2 (UCP2) and mitochondrial function. As an inhibitor of UCP2, genipin increases mitochondrial membrane potential and ATP production. It also has anti-inflammatory activity by modulating NF-κB signaling and reducing the production of inflammatory cytokines. Genipin's crosslinking properties are used in biomedical applications, such as tissue engineering and drug delivery.
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| ln Vitro |
In island cells, genipin promotes insulin production, blocks KATP channels, raises ATP levels, and enhances Mediterranean docking. By blocking insulin signaling through JNK activation of c-Jun N JNK and serine phosphorylation of JNK substrate-1 (IRS-1), genipin reduces the amount of insulin that is activated in 3T3-L1 adipocytes [1]. Genipin causes an increase in micronutrients and the translocation of the C2C12 myotube potential transporter 4 (GLUT4) by activating IRS-1, PI3-K, and downstream signaling pathways and raising calcium concentrations [1]. When FaO cells were treated with genipin, the amount of cytochrome c in their cytoplasm dramatically increased. Activation of caspase-3 and caspase-7 eventually causes genipin to imitate the processes involved in cellular vision. When 200 μM genipin was applied to Hep3B cells, the amount of ROS was noticeably higher [2].
In vitro, genipin has been shown to have anti-inflammatory, antioxidant, and neuroprotective effects. It inhibits the production of inflammatory cytokines and reduces oxidative stress in various cell types. Genipin also inhibits UCP2 activity, increasing mitochondrial membrane potential. Its crosslinking properties have been demonstrated in various biomedical applications. |
| ln Vivo |
In vivo, genipin has been studied for its potential therapeutic applications in liver diseases, neurodegenerative diseases, and diabetes. It has hepatoprotective effects in models of liver injury. Genipin has also shown neuroprotective effects in models of neurodegenerative diseases. The compound has anti-diabetic effects by improving insulin sensitivity.
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| Enzyme Assay |
In vitro enzyme or receptor binding assays for genipin involve measuring its inhibition of UCP2 activity. The assay uses isolated mitochondria or purified UCP2 and measures the effect of the compound on mitochondrial respiration and membrane potential. The compound's anti-inflammatory activity is assessed by measuring the production of inflammatory cytokines in immune cells.
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| Cell Assay |
In vitro cell-based assays for genipin are performed using various cell lines, including hepatocytes, neurons, and immune cells. Cells are treated with the compound, and cell viability, apoptosis, and inflammatory responses are assessed. The compound's effects on mitochondrial function and UCP2 activity are measured.
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| Animal Protocol |
In vivo animal experiments for genipin are conducted using rodent models of liver injury, neurodegenerative diseases, and diabetes. The compound is administered orally or intraperitoneally. Liver enzymes, oxidative stress markers, and inflammatory cytokines are measured in tissue samples. Cognitive function is assessed in models of neurodegenerative diseases.
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| ADME/Pharmacokinetics |
Pharmacokinetic (PK) properties of genipin indicate that it has a molecular weight of 226.23 and a molecular formula of C11H14O5. It is a solid at room temperature. The compound is soluble in DMSO and other organic solvents. It is metabolized in the liver and excreted renally. The compound is typically stored at -20°C.
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| Toxicity/Toxicokinetics |
Toxicology (toxicology) data for genipin indicate that it is generally well-tolerated at moderate doses. As a natural compound, it has a favorable safety profile. However, high doses may cause gastrointestinal disturbances and hepatotoxicity. The compound should be used with caution in patients with liver disease.
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| References |
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| Additional Infomation |
Genipin is a cyclopentadiene monoterpene compound. It possesses a variety of activities, including acting as an uncoupling protein inhibitor, hepatotoxic agent, apoptosis inhibitor, antioxidant, anti-inflammatory agent, and cross-linking agent. Genipin has been reported to be found in gardenia, eucommia, and other organisms with relevant data.
Other information: Genipin is an aglycone derived from geniposide, found in Gardenia jasminoides. It is a naturally occurring crosslinking agent and an inhibitor of UCP2. The compound has anti-inflammatory, antioxidant, neuroprotective, and hepatoprotective effects. Its CAS number is 6902-77-8. |
| Molecular Formula |
C11H14O5
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| Molecular Weight |
226.228
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| Exact Mass |
226.084
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| CAS # |
6902-77-8
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| PubChem CID |
442424
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
416.0±45.0 °C at 760 mmHg
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| Melting Point |
106-108 °C(lit.)
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| Flash Point |
164.9±22.2 °C
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| Vapour Pressure |
0.0±2.2 mmHg at 25°C
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| Index of Refraction |
1.565
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| LogP |
0.12
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
16
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| Complexity |
357
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| Defined Atom Stereocenter Count |
3
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| SMILES |
COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O
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| InChi Key |
AZKVWQKMDGGDSV-BCMRRPTOSA-N
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| InChi Code |
InChI=1S/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7-,9-,11-/m1/s1
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| Chemical Name |
methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
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| Synonyms |
(+)-Genipin; Genipin
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
DMSO : ≥ 100 mg/mL (~442.03 mM)
H2O : ~4 mg/mL (~17.68 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.05 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (11.05 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (11.05 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 9.09 mg/mL (40.18 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4203 mL | 22.1014 mL | 44.2028 mL | |
| 5 mM | 0.8841 mL | 4.4203 mL | 8.8406 mL | |
| 10 mM | 0.4420 mL | 2.2101 mL | 4.4203 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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