Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H26O4 |
| Molecular Weight | 294.3859 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC[C@H](O)CC(=O)CCC1=CC=C(O)C(OC)=C1
InChI
InChIKey=NLDDIKRKFXEWBK-AWEZNQCLSA-N
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
DescriptionCurator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT01344538 | https://www.ncbi.nlm.nih.gov/pubmed/24552266 | https://clinicaltrials.gov/ct2/show/NCT03268655 | https://www.ncbi.nlm.nih.gov/pubmed/28349496
Curator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT01344538 | https://www.ncbi.nlm.nih.gov/pubmed/24552266 | https://clinicaltrials.gov/ct2/show/NCT03268655 | https://www.ncbi.nlm.nih.gov/pubmed/28349496
Gingerol (6-Gingerol) is bioactive compound found in ginger (Zingiber officinale) with antioxidant activity, which functions as an anti-inflammatory and antitumor agent. 6-Gingerol has been found to possess anticancer activities via its effect on a variety of biological pathways involved in apoptosis, cell cycle regulation, cytotoxic activity, and inhibition of angiogenesis. Gingerol has been investigated for its effect on cancerous tumors in the bowel, breast tissue, ovaries, the pancreas, among other tissues, with positive results. In phase II clinical trials Gingerol was successfully studied for preventing chemotherapy- induced nausea and vomiting in patients receiving highly emetogenic chemotherapy.
Originator
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18708382/ |
21.5 mg single, oral dose: 21.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
GINGEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.85 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18708382/ |
43 mg single, oral dose: 43 mg route of administration: Oral experiment type: SINGLE co-administered: |
GINGEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.69 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18708382/ |
32.25 mg single, oral dose: 32.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
GINGEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
12.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18708382/ |
21.5 mg single, oral dose: 21.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
GINGEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
65.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18708382/ |
43 mg single, oral dose: 43 mg route of administration: Oral experiment type: SINGLE co-administered: |
GINGEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
75.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18708382/ |
32.25 mg single, oral dose: 32.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
GINGEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
110 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18708382/ |
43 mg single, oral dose: 43 mg route of administration: Oral experiment type: SINGLE co-administered: |
GINGEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes. | 2001 Mar |
|
| [HPLC determination of 6-gingerol in Rhizoma Zingiberis Recens]. | 2002 May |
|
| Modifications of capsaicin-sensitive neurons in isolated guinea pig ileum by [6]-gingerol and lafutidine. | 2003 Aug |
|
| Extraction of chili, black pepper, and ginger with near-critical CO2, propane, and dimethyl ether: analysis of the extracts by quantitative nuclear magnetic resonance. | 2003 Aug 13 |
|
| Chemoprevention: eat ginger, rub on pomegranate. | 2003 Dec |
|
| Analysis of a ginger extract by high-performance liquid chromatography coupled to nuclear magnetic resonance spectroscopy using superheated deuterium oxide as the mobile phase. | 2003 Mar 28 |
|
| Bioassay-guided isolation and identification of antifungal compounds from ginger. | 2003 Sep |
|
| Suppression of the nuclear factor-kappaB activation pathway by spice-derived phytochemicals: reasoning for seasoning. | 2004 Dec |
|
| [6]-Gingerol inhibits COX-2 expression by blocking the activation of p38 MAP kinase and NF-kappaB in phorbol ester-stimulated mouse skin. | 2005 Apr 7 |
|
| Induction of an epithelial to mesenchymal transition in human immortal and malignant keratinocytes by TGF-beta1 involves MAPK, Smad and AP-1 signalling pathways. | 2005 Aug 1 |
|
| Cancer preventive role of selected dietary factors. | 2005 Jan-Mar |
|
| Mechanism of inhibition of peroxynitrite-induced oxidation and nitration by [6]-gingerol. | 2005 Jun |
|
| Prokinetic effect of a Kampo medicine, Hange-koboku-to (Banxia-houpo-tang), on patients with functional dyspepsia. | 2005 Nov |
|
| Instrument dependence of electrospray ionization and tandem mass spectrometric fragmentation of the gingerols. | 2006 |
|
| [6]-Gingerol induces cell cycle arrest and cell death of mutant p53-expressing pancreatic cancer cells. | 2006 Oct 31 |
|
| In vitro and in vivo modulation of testosterone mediated alterations in apoptosis related proteins by [6]-gingerol. | 2007 Dec |
|
| Indian herbal medicines: possible potent therapeutic agents for rheumatoid arthritis. | 2007 Jul |
|
| Cancer preventive properties of ginger: a brief review. | 2007 May |
|
| Cytotoxic components from the dried rhizomes of Zingiber officinale Roscoe. | 2008 Apr |
|
| 6-Shogaol and 6-gingerol, the pungent of ginger, inhibit TNF-alpha mediated downregulation of adiponectin expression via different mechanisms in 3T3-L1 adipocytes. | 2008 Aug 29 |
|
| 6-Shogaol suppressed lipopolysaccharide-induced up-expression of iNOS and COX-2 in murine macrophages. | 2008 Dec |
|
| 6-Shogaol induces apoptosis in human colorectal carcinoma cells via ROS production, caspase activation, and GADD 153 expression. | 2008 May |
|
| [6]-Gingerol inhibits metastasis of MDA-MB-231 human breast cancer cells. | 2008 May |
|
| Cancer is a preventable disease that requires major lifestyle changes. | 2008 Sep |
Sample Use Guides
The HUVECs were used for activity evaluation. The HUVECs were cultured in Minimum Essential Medium (MEM) containing 10% fetal bovine serum, penicillin (100 mkg/mkL), streptomycin (100 mg/mL) in a 5% carbon dioxide atmosphere at 37C. For each experiment, cells were treated with 6-gingerol (10 mkM) for 1 h and then exposed to MEHP (10, 20, and 40 mkM) for 24 h.
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1626 (Number of products:14)
Created by
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442793
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GINGEROL
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10136
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23513-14-6
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C007845
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m5729
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DTXSID3041035
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925QK2Z900
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SUBSTANCE RECORD
