![(Rac)-[6]-Gingerol](/upload/0319/V111175.png)
| Targets |
(Rac)-[6]-Gingerol interacts with multiple molecular targets. It suppresses spontaneous Ca2+ spikes and isometric contraction in smooth muscle, indicating effects on calcium signaling pathways. It exerts its anti-inflammatory activity by inhibiting the production of pro-inflammatory cytokines (e.g., TNF-alpha, IL-6) and suppressing the activity of enzymes like cyclooxygenase-2 (COX-2). Its anticancer effects are mediated through the induction of apoptosis and cell cycle arrest.
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| ln Vitro |
In vitro, (Rac)-[6]-Gingerol exhibits moderate anticancer activity against a range of human cancer cell lines, including lung, ovarian, melanoma, and colon cancer. It has potent anti-inflammatory activity by inhibiting key pro-inflammatory enzymes (COX-2) and cytokines. It also shows antihepatotoxic effects, protecting the liver from damage. As an antioxidant, it protects cells like HL-60 from oxidative stress.
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| ln Vivo |
In animal studies, [6]-Gingerol (the non-racemic active constituent) has demonstrated significant health benefits. These include anti-inflammatory activity in models of acute inflammation, protective effects in models of bowel, breast, and pancreatic tumors, and hepatoprotective effects. The racemic mixture is expected to have similar in vivo properties, although the specific enantiomer responsible for the activity is not specified.
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| Enzyme Assay |
No specific enzyme assay for (Rac)-[6]-Gingerol is detailed, but COX-2 inhibition can be measured. The enzyme (COX-2) is incubated with arachidonic acid and serial dilutions of (Rac)-[6]-Gingerol. Prostaglandin E2 (PGE2) production is measured by ELISA. The IC50 is the concentration inhibiting 50% of PGE2 production compared to a control. The antioxidant capacity is measured by its ability to scavenge the DPPH radical.
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| Cell Assay |
The anticancer activity of (Rac)-[6]-Gingerol is evaluated using the MTT assay. Cancer cells (e.g., A549, HeLa) are seeded in 96-well plates and allowed to attach. The cells are then treated with various concentrations of (Rac)-[6]-Gingerol (0-200 uM) for 48-72 h. Cell viability is determined by MTT reduction. The IC50 values for various cancer cell lines can be calculated. This assay would confirm its antiproliferative effects.
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| Animal Protocol |
In a mouse model of inflammation (e.g., carrageenan-induced paw edema), the in vivo activity of (Rac)-[6]-Gingerol can be evaluated. Male ICR mice are injected with 1% carrageenan into the right hind paw. One hour before the injection, mice are treated orally with (Rac)-[6]-Gingerol (e.g., 10-100 mg/kg) or vehicle. Paw thickness is measured at 1, 2, 3, and 4 hours after the carrageenan challenge. A reduction in paw edema compared to the vehicle control indicates anti-inflammatory activity.
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| ADME/Pharmacokinetics |
No specific PK data are provided for (Rac)-[6]-Gingerol. For the natural product [6]-Gingerol, it is known to be rapidly metabolized and has low oral bioavailability. It is extensively conjugated in the liver to form glucuronides and sulfates. Its plasma half-life in rodents is short (< 1 h). These properties limit its use as a drug.
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| Toxicity/Toxicokinetics |
No specific toxicology data are provided. As a natural food product, ginger and its extracts have a long history of safe use. The isolated compound, [6]-Gingerol, has been tested in some studies and was generally well-tolerated at doses used to demonstrate efficacy. It is not a drug and is not regulated as one. High doses of ginger extract may cause mild gastrointestinal side effects (e.g., heartburn, diarrhea).
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| References | |
| Additional Infomation |
(Rac)-[6]-Gingerol (CAS# 39886-76-5) is a research-grade natural product. It is a racemic mixture of [6]-Gingerol, the primary bioactive compound in ginger. It is not an FDA-approved drug. Due to its broad spectrum of biological activities, it is a valuable tool for nutraceutical research and for studying pathways related to inflammation, oxidative stress, and cancer. For research use only.
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| Molecular Formula |
C17H26O4
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| Molecular Weight |
294.39
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| Exact Mass |
294.183
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| CAS # |
39886-76-5
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| Related CAS # |
[6]-Gingerol; 23513-14-6
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| PubChem CID |
3473
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| Appearance |
Typically exists as solids at room temperature
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| Melting Point |
30 - 32 °C
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| Hydrogen Bond Donor Count |
2
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| Rotatable Bond Count |
10
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| Heavy Atom Count |
21
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| Complexity |
293
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCCC(CC(=O)CCC1=CC(=C(C=C1)O)OC)O
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| InChi Key |
NLDDIKRKFXEWBK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3
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| Chemical Name |
5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
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| Synonyms |
(Rac)-[6]-Gingerol; (±)-[6]-Gingerol
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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 | 3.3969 mL | 16.9843 mL | 33.9685 mL | |
| 5 mM | 0.6794 mL | 3.3969 mL | 6.7937 mL | |
| 10 mM | 0.3397 mL | 1.6984 mL | 3.3969 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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