Physicochemical Properties
| Molecular Formula | C17H26O4 |
| Molecular Weight | 294.3859 |
| Exact Mass | 294.183 |
| Elemental Analysis | C, 69.36; H, 8.90; O, 21.74 |
| CAS # | 23513-14-6 |
| Related CAS # | 23513-14-6 |
| PubChem CID | 442793 |
| Appearance | White to off-white solid |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 453.0±35.0 °C at 760 mmHg |
| Melting Point | 30 - 32ºC |
| Flash Point | 159.0±19.4 °C |
| Vapour Pressure | 0.0±1.2 mmHg at 25°C |
| Index of Refraction | 1.523 |
| LogP | 2.48 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 10 |
| Heavy Atom Count | 21 |
| Complexity | 293 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | O([H])[C@]([H])(C([H])([H])C(C([H])([H])C([H])([H])C1C([H])=C([H])C(=C(C=1[H])OC([H])([H])[H])O[H])=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] |
| InChi Key | NLDDIKRKFXEWBK-AWEZNQCLSA-N |
| 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/t14-/m0/s1 |
| Chemical Name | (5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one |
| Synonyms | 6-Gingerol |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| Targets | AMPK; Apoptosis |
| ln Vitro | In a dose-dependent manner, treatment with 6-gingerol significantly lowers the LoVo human colon cancer cell's ability to proliferate. In LoVo cells, 6-gingerol strongly induces G2/M phase arrest and only slightly affects sub-G1 phase. Cyclin A, cyclin B1, and CDK1 levels are decreased; however, the negative cell cycle regulators p27Kip1 and p21Cip1 are elevated as a result of 6-gingerol treatment. Furthermore, treatment with 6-gingerol increases p53 phosphorylation and intracellular reactive oxygen species (ROS). As well as the later stages of carcinogenesis, such as angiogenesis and metastasis, 6-gingerol is effective at suppressing the transformation, hyperproliferation, and inflammatory processes that cause and promote carcinogenesis[1]. 6-gingerol has direct cytotoxic effects on cultures of tumor cells, such as colorectal cancer cells, HL-60 cells and breast cancer cells[2]. |
| ln Vivo | 6-gingerol inhibits tumor growth in several types of murine tumors, such as B16F1 melanomas, Renca renal cell carcinomas and CT26 colon carcinomas, established by inoculating tumor cells on the flanks of mice, although it does not lead to complete eradication of the tumors. 6-gingerol treatment of tumor-bearing mice results in massive infiltration of CD4 and CD8 T-cells and B220+ B-cells, but decreases the number of CD4+Foxp3+ regulatory T-cells. In 6-gingerol-treated mice, the CD8 tumor-infiltrating T lymphocytes exhibit high levels of IFN-, a CTL CD107a cell activation marker, and chemokine receptors CXCR3 and CCR5 that are expressed on TH1 cells[2]. |
| Cell Assay | A cell line for colon cancer The DMEM supplemented with 10% fetal bovine serum, 1% non-essential amino acids, 1% L-glutamine, and 100 μg/mL penicillin/streptomycin is used to maintain LoVo at 37°C in a humid environment with 5% CO2. Approximately 80% confluence is reached after cell growth in 10 cm Petri dishes that were initially seeded with 2 105 cells per mL. After that, the cells are gathered for the subsequent analyses, such as the analyses of cell viability, flow cytometry, and immunoblotting. In order to treat cells with 6-gingerol, cells are first starved for 24 hours (h) in serum-free DMEM, and then they are incubated for 24 or 48 hours with 6-gingerol at a series of concentrations (1, 5, 10, and 15 μg/mL) in the same medium. |
| Animal Protocol | Mice: For 14 days, different oral dosages of [6]-gingerol were administered to mice with colitis brought on by the DSS. The level of proinflammatory cytokines in colon tissues is measured, and body weight and colon inflammation are assessed[2]. |
| References |
[1]. 6-Gingerol Inhibits Growth of Colon Cancer Cell LoVo via Induction of G2/M Arrest [2]. Int J Cancer . 2012 Jun 1;130(11):2618-28. |
| Additional Infomation |
Gingerol is a beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger. It has a role as an antineoplastic agent and a plant metabolite. It is a beta-hydroxy ketone and a member of guaiacols. Gingerol has been reported in Cuminum cyminum, Aframomum melegueta, and other organisms with data available. See also: Ginger (part of); (S)-6-Gingerol (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | DMSO: 50~58 mg/mL (169.8~197 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.49 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 (8.49 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (8.49 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. Solubility in Formulation 4: 25 mg/mL (84.92 mM) in 50% PEG300 50% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (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 |