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 |
|---|---|---|
| Effect of ginger constituents and synthetic analogues on cyclooxygenase-2 enzyme in intact cells. | 2001 Jun |
|
| The stability of gingerol and shogaol in aqueous solutions. | 2001 Oct |
|
| Structure-antiemetic-activity of some diarylheptanoids and their analogues. | 2002 Mar |
|
| 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 |
|
| Bioassay-guided isolation and identification of antifungal compounds from ginger. | 2003 Sep |
|
| Dietary ginger constituents, galanals A and B, are potent apoptosis inducers in Human T lymphoma Jurkat cells. | 2003 Sep 25 |
|
| Ginger (Zingiber officinale Roscoe) and the gingerols inhibit the growth of Cag A+ strains of Helicobacter pylori. | 2003 Sep-Oct |
|
| Enhancement of insulin sensitivity in adipocytes by ginger. | 2004 |
|
| Protective role of vanilloid receptor type 1 in HCl-induced gastric mucosal lesions in rats. | 2004 Apr |
|
| Diarylheptanoids from the rhizomes of Zingiber officinale. | 2004 Apr |
|
| 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 |
|
| Commercially processed dry ginger (Zingiber officinale): composition and effects on LPS-stimulated PGE2 production. | 2005 Jul |
|
| Mechanism of inhibition of peroxynitrite-induced oxidation and nitration by [6]-gingerol. | 2005 Jun |
|
| Cytotoxic and apoptotic activities of diarylheptanoids and gingerol-related compounds from the rhizome of Chinese ginger. | 2005 Nov 14 |
|
| [6]-Gingerol, a pungent ingredient of ginger, inhibits angiogenesis in vitro and in vivo. | 2005 Sep 23 |
|
| Instrument dependence of electrospray ionization and tandem mass spectrometric fragmentation of the gingerols. | 2006 |
|
| Synergistic effect of [10]-gingerol and aminoglycosides against vancomycin-resistant enterococci (VRE). | 2006 Mar |
|
| Indian herbal medicines: possible potent therapeutic agents for rheumatoid arthritis. | 2007 Jul |
|
| [6]-Gingerol prevents UVB-induced ROS production and COX-2 expression in vitro and in vivo. | 2007 May |
|
| Ginger ingredients reduce viability of gastric cancer cells via distinct mechanisms. | 2007 Oct 12 |
|
| Screening of biochemical modulator by tumor cell permeability of doxorubicin. | 2008 Apr 16 |
|
| Plasma pharmacokinetics and tissue distribution of [6]-gingerol in rats. | 2008 Dec |
|
| Effects of spice constituents on P-glycoprotein-mediated transport and CYP3A4-mediated metabolism in vitro. | 2008 Jul |
|
| Inhibitory effect of gingerol on the proliferation and invasion of hepatoma cells in culture. | 2008 Jun |
|
| Multiple mechanisms are involved in 6-gingerol-induced cell growth arrest and apoptosis in human colorectal cancer cells. | 2008 Mar |
|
| 6-Shogaol induces apoptosis in human colorectal carcinoma cells via ROS production, caspase activation, and GADD 153 expression. | 2008 May |
|
| Antibacterial activity of [10]-gingerol and [12]-gingerol isolated from ginger rhizome against periodontal bacteria. | 2008 Nov |
|
| Cancer is a preventable disease that requires major lifestyle changes. | 2008 Sep |
|
| Differential growth suppression of human melanoma cells by tea (Camellia sinensis) epicatechins (ECG, EGC and EGCG). | 2009 Dec |
|
| Modulation of macrophage functions by compounds isolated from Zingiber officinale. | 2009 Feb |
|
| Simultaneous determination of 6-gingerol, 8-gingerol, 10-gingerol and 6-shogaol in rat plasma by liquid chromatography-mass spectrometry: Application to pharmacokinetics. | 2009 Mar 15 |
|
| Ginger's (Zingiber officinale Roscoe) inhibition of rat colonic adenocarcinoma cells proliferation and angiogenesis in vitro. | 2009 May |
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.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
DSLD |
1626 (Number of products:14)
Created by
admin on Fri Dec 15 17:16:59 GMT 2023 , Edited by admin on Fri Dec 15 17:16:59 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
442793
Created by
admin on Fri Dec 15 17:17:00 GMT 2023 , Edited by admin on Fri Dec 15 17:17:00 GMT 2023
|
PRIMARY | |||
|
GINGEROL
Created by
admin on Fri Dec 15 17:17:00 GMT 2023 , Edited by admin on Fri Dec 15 17:17:00 GMT 2023
|
PRIMARY | |||
|
10136
Created by
admin on Fri Dec 15 17:16:59 GMT 2023 , Edited by admin on Fri Dec 15 17:16:59 GMT 2023
|
PRIMARY | |||
|
23513-14-6
Created by
admin on Fri Dec 15 17:16:59 GMT 2023 , Edited by admin on Fri Dec 15 17:16:59 GMT 2023
|
PRIMARY | |||
|
C007845
Created by
admin on Fri Dec 15 17:16:59 GMT 2023 , Edited by admin on Fri Dec 15 17:16:59 GMT 2023
|
PRIMARY | |||
|
m5729
Created by
admin on Fri Dec 15 17:16:59 GMT 2023 , Edited by admin on Fri Dec 15 17:16:59 GMT 2023
|
PRIMARY | Merck Index | ||
|
DTXSID3041035
Created by
admin on Fri Dec 15 17:16:59 GMT 2023 , Edited by admin on Fri Dec 15 17:16:59 GMT 2023
|
PRIMARY | |||
|
925QK2Z900
Created by
admin on Fri Dec 15 17:16:59 GMT 2023 , Edited by admin on Fri Dec 15 17:16:59 GMT 2023
|
PRIMARY |
SUBSTANCE RECORD
