| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 100mg |
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| Targets |
VR1 (vanilloid receptor subtype-1, capsaicin-activated receptor) – EC50 for plasma membrane current induction: 5.0 ± 0.6 μM [1]
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| ln Vitro |
Induced capsaicin-like increases in plasma membrane conductance exclusively in capsaicin-sensitive DRG neurones, with a reversal potential of -6 ± 2 mV. The maximum current induced by 8-Gingerol was 96 ± 7% of that induced by a maximal concentration of capsaicin (10 μM), indicating it is likely a full agonist. Concentration-response curve determined at a holding potential of +40 mV to minimize Ca2+ entry and desensitization; currents normalized to those produced by 10 μM capsaicin in each cell. EC50 for plasma membrane current induction was 5.0 ± 0.6 μM. Currents evoked by 1 μM 8-Gingerol were almost completely blocked (>99% reduction) by pre-application of 10 μM capsazepine, a VR1 receptor antagonist. [1]
Preincubation of DRG neurones with 8-Gingerol (10 μM) evoked a capsaicin-like increase in intracellular Ca2+ transients, measured using Fluo-4 fluorescence. This effect was blocked by pre-treatment with 10 μM capsazepine. [1] 8-Gingerol (along with [8]-paradol and [8]-shogaol) was identified as a potent inhibitor of cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2). Specifically, [8]-paradox, [8]-shogaol, and [8]-gingerol were potent inhibitors of COX-2. [2] 8-Gingerol potently inhibited platelet aggregation induced by arachidonic acid, ADP, epinephrine, and collagen. It was more potent than aspirin in a COX-1 inhibitor assay. [2] 8-Gingerol (along with [6]-gingerol and [8]-shogaol) inhibited the growth of 19 strains of Helicobacter pylori (including five CagA+ strains) in vitro. [2] 8-Gingerol (along with [6]-shogaol) was identified as a component that kills Anisakis larvae in vitro, leading to destruction of the digestive tract and disturbances of the cuticle. [2] |
| Enzyme Assay |
The activity of ginger constituents, including 8-Gingerol, on cyclooxygenase (COX) enzymes was assessed. For the COX-1 inhibitor assay, the ability of compounds to inhibit the conversion of arachidonic acid to prostaglandins was measured. 8-Gingerol was found to be a potent inhibitor, showing greater potency than aspirin. For COX-2, 8-Gingerol was identified as a potent inhibitor, along with [8]-paradox and [8]-shogaol. [2]
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| Cell Assay |
Dorsal root ganglion (DRG) neurones were isolated from neonatal (3-5 day old) rats and cultured overnight. For intracellular calcium measurement using Fluo-4, cells were incubated with 10 μM Fluo-4 for 15 min at 37°C. Neurones were first exposed to a low dose of capsaicin (100 nM) for 5-10 seconds to identify capsaicin-sensitive neurones, followed by addition of 8-Gingerol (10 μM). Fluorescence changes were recorded every 2 seconds. In capsazepine antagonism experiments, neurones were exposed to capsaicin, washed, then capsazepine (10 μM), gingerol, and capsaicin were added sequentially. A 3-minute wash was employed between each addition of drugs. Calcium transients were represented as a ratio F/Fmax versus time. 8-Gingerol (10 μM) evoked a clear increase in [Ca2+]i, which was blocked by pre-treatment with capsazepine. [1]
For electrophysiological studies, whole-cell patch-clamp recordings were performed on cultured DRG neurones. Micropipettes were filled with a solution containing (in mM): CsCl 130, NaCl 5, HEPES 10, EGTA 10, CaCl2 2, MgATP 5, NaGTP 0.3 (pH 7.3). The external bathing solution contained (in mM): NaCl 140, KCl 5, CaCl2 2, MgCl2 1, HEPES 10, glucose 10 (pH 7.4). To determine concentration-response curves, agonists were applied at increasing concentrations while the cell was voltage-clamped at +40 mV to minimize Ca2+ entry and desensitization. Currents were normalized to those produced by 10 μM capsaicin in each cell. 8-Gingerol induced plasma membrane currents with an EC50 of 5.0 ± 0.6 μM. Currents evoked by 1 μM 8-Gingerol were almost completely blocked by pre-application of 10 μM capsazepine. [1] |
| References | |
| Additional Infomation |
8-Gingerol is a β-hydroxy ketone, belonging to the phenolic and monomethoxybenzene classes. It has been reported that ginger (Zingiber officinale) contains 8-gingerol, and relevant data are available. See also: Ginger (partial).
8-Gingerol is a pungent constituent of ginger (Zingiber officinale). Its potency for activating the VR1 receptor increases with increasing size of the side chain and overall hydrophobicity; [8]-gingerol (Log P = 2.88, side chain C8) is approximately 10-fold more potent than [6]-gingerol (Log P = 1.90, side chain C6) in inducing plasma membrane currents. In contrast, zingerone, which lacks the side chain, was dramatically less active (at 1 mM, produced only ~10% of the maximal capsaicin current). The presence of the hydroxyl moiety at the C5 position in the 'B' region and substitution with an amide function (as in capsaicin) may influence potency. [1] The discovery of gingerols as VR1 receptor agonists may explain the traditional use of ginger for pain relief in rheumatic and inflammatory conditions. The presence of VR1 receptors in the brainstem (nausea centre) may also be associated with ginger's use as an antiemetic. [1] The gingerol structure may be used as a template for developing moderately potent activators of the VR1 receptor. [1] Zingiberis rhizoma (ginger) is used as a broad-spectrum antiemetic. Clinical evidence for its effectiveness is most robust for pregnancy-related nausea and vomiting. While ginger constituents interfere with the inflammatory cascade and the vanilloid nociceptor (VR1), clinical usefulness for osteoarthritis or other pain remains to be confirmed. [2] |
| Molecular Formula |
C19H30O4
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|---|---|
| Molecular Weight |
322.4391
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| Exact Mass |
322.214
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| CAS # |
23513-08-8
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| PubChem CID |
168114
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| Appearance |
White to yellow solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
476.4±35.0 °C at 760 mmHg
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| Melting Point |
30 - 32 °C
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| Flash Point |
162.6±19.4 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.517
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| LogP |
3.55
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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 |
12
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| Heavy Atom Count |
23
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| Complexity |
319
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CCCCCCC[C@@H](CC(=O)CCC1=CC(=C(C=C1)O)OC)O
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| InChi Key |
BCIWKKMTBRYQJU-INIZCTEOSA-N
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| InChi Code |
InChI=1S/C19H30O4/c1-3-4-5-6-7-8-16(20)14-17(21)11-9-15-10-12-18(22)19(13-15)23-2/h10,12-13,16,20,22H,3-9,11,14H2,1-2H3/t16-/m0/s1
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| Chemical Name |
(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one
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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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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 (~310.14 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.75 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 (7.75 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 (7.75 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1014 mL | 15.5068 mL | 31.0135 mL | |
| 5 mM | 0.6203 mL | 3.1014 mL | 6.2027 mL | |
| 10 mM | 0.3101 mL | 1.5507 mL | 3.1014 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05882864 | NOT YET RECRUITING | Drug: 6-Gingerol Drug: Triamcinolone Acetonide 0.1% Oromucosal Paste |
Oral Lichen Planus | Ain Shams University | 2023-08-01 | Phase 4 |
| NCT03698318 | COMPLETED | Dietary Supplement: Tested product n°1 Dietary Supplement: Tested product n°2 Dietary Supplement: Tested product n°3 |
Healthy Subject | Givaudan France Naturals | 2018-10-15 | Not Applicable |
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