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
| Molecular Formula | C17H26O4 |
| Molecular Weight | 294.3859 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|---|---|
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 |
|
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 |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
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 |
|---|---|---|
| Differential growth suppression of human melanoma cells by tea (Camellia sinensis) epicatechins (ECG, EGC and EGCG). | 2009-12 |
|
| Ginger's (Zingiber officinale Roscoe) inhibition of rat colonic adenocarcinoma cells proliferation and angiogenesis in vitro. | 2009-05 |
|
| Simultaneous determination of 6-gingerol, 8-gingerol, 10-gingerol and 6-shogaol in rat plasma by liquid chromatography-mass spectrometry: Application to pharmacokinetics. | 2009-03-15 |
|
| Modulation of macrophage functions by compounds isolated from Zingiber officinale. | 2009-02 |
|
| Plasma pharmacokinetics and tissue distribution of [6]-gingerol in rats. | 2008-12 |
|
| 6-Shogaol suppressed lipopolysaccharide-induced up-expression of iNOS and COX-2 in murine macrophages. | 2008-12 |
|
| Antibacterial activity of [10]-gingerol and [12]-gingerol isolated from ginger rhizome against periodontal bacteria. | 2008-11 |
|
| Specific reaction of alpha,beta-unsaturated carbonyl compounds such as 6-shogaol with sulfhydryl groups in tubulin leading to microtubule damage. | 2008-10-15 |
|
| Muscarinic, Ca(++) antagonist and specific butyrylcholinesterase inhibitory activity of dried ginger extract might explain its use in dementia. | 2008-10 |
|
| Cancer is a preventable disease that requires major lifestyle changes. | 2008-09 |
|
| 6-Shogaol and 6-gingerol, the pungent of ginger, inhibit TNF-alpha mediated downregulation of adiponectin expression via different mechanisms in 3T3-L1 adipocytes. | 2008-08-29 |
|
| Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects. | 2008-08 |
|
| Changes in the contents of oleoresin and pungent bioactive principles of Jamaican ginger (Zingiber officinale Roscoe.) during maturation. | 2008-07-23 |
|
| Analysis of anti-platelet aggregation components of Rhizoma Zingiberis using chicken thrombocyte extract and high performance liquid chromatography. | 2008-07-05 |
|
| Effects of spice constituents on P-glycoprotein-mediated transport and CYP3A4-mediated metabolism in vitro. | 2008-07 |
|
| Inhibitory effect of gingerol on the proliferation and invasion of hepatoma cells in culture. | 2008-06 |
|
| [RP-HPLC fingerprint evaluating different ginger juice as processing material]. | 2008-05 |
|
| 6-Shogaol induces apoptosis in human colorectal carcinoma cells via ROS production, caspase activation, and GADD 153 expression. | 2008-05 |
|
| [6]-Gingerol inhibits metastasis of MDA-MB-231 human breast cancer cells. | 2008-05 |
|
| Screening of biochemical modulator by tumor cell permeability of doxorubicin. | 2008-04-16 |
|
| Systemic administration of [6]-gingerol, a pungent constituent of ginger, induces hypothermia in rats via an inhibitory effect on metabolic rate. | 2008-04-14 |
|
| Cytotoxic components from the dried rhizomes of Zingiber officinale Roscoe. | 2008-04 |
|
| Multiple mechanisms are involved in 6-gingerol-induced cell growth arrest and apoptosis in human colorectal cancer cells. | 2008-03 |
|
| [6]-gingerol induces Ca2+ mobilization in Madin-Darby canine kidney cells. | 2008-01 |
|
| In vitro synthesis of curcuminoids by type III polyketide synthase from Oryza sativa. | 2007-12-28 |
|
| Ginger inhibits cell growth and modulates angiogenic factors in ovarian cancer cells. | 2007-12-20 |
|
| Evaluation of the topical anti-inflammatory activity of ginger dry extracts from solutions and plasters. | 2007-12 |
|
| In vitro and in vivo modulation of testosterone mediated alterations in apoptosis related proteins by [6]-gingerol. | 2007-12 |
|
| Induction of multiple antibiotic resistance in Bacteroides fragilis by benzene and benzene-derived active compounds of commonly used analgesics, antiseptics and cleaning agents. | 2007-12 |
|
| Stability of [6]-gingerol and [6]-shogaol in simulated gastric and intestinal fluids. | 2007-11-30 |
|
| Liquid chromatographic determination of 6-, 8-, 10-gingerol, and 6-shogaol in ginger (Zingiber officinale) as the raw herb and dried aqueous extract. | 2007-10-25 |
|
| Ginger ingredients reduce viability of gastric cancer cells via distinct mechanisms. | 2007-10-12 |
|
| High-performance liquid chromatographic analysis of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol in ginger-containing dietary supplements, spices, teas, and beverages. | 2007-09-01 |
|
| TRP channels and pain. | 2007-08 |
|
| Indian herbal medicines: possible potent therapeutic agents for rheumatoid arthritis. | 2007-07 |
|
| Antioxidant actions of phenolic compounds found in dietary plants on low-density lipoprotein and erythrocytes in vitro. | 2007-06 |
|
| Chemopreventive anti-inflammatory activities of curcumin and other phytochemicals mediated by MAP kinase phosphatase-5 in prostate cells. | 2007-06 |
|
| [6]-Gingerol prevents UVB-induced ROS production and COX-2 expression in vitro and in vivo. | 2007-05 |
|
| Activation of TRPA1 channels by the fatty acid amide hydrolase inhibitor 3'-carbamoylbiphenyl-3-yl cyclohexylcarbamate (URB597). | 2007-05 |
|
| Cancer preventive properties of ginger: a brief review. | 2007-05 |
|
| Effect of 6-gingerol on pro-inflammatory cytokine production and costimulatory molecule expression in murine peritoneal macrophages. | 2007-04 |
|
| Microsomal hydroxylation and glucuronidation of [6]-gingerol. | 2006-11-15 |
|
| [6]-Gingerol induces cell cycle arrest and cell death of mutant p53-expressing pancreatic cancer cells. | 2006-10-31 |
|
| Determination of 6-gingerol in ginger (Zingiber officinale) using high-performance thin-layer chromatography. | 2006-10 |
|
| Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases. | 2006-09 |
|
| [Effect of gingerol on endotoxemia mouse model induced by heatstroke]. | 2006-06 |
|
| Variation in concentration and labeling of ginger root dietary supplements. | 2006-06 |
|
| Gingerol metabolite and a synthetic analogue Capsarol inhibit macrophage NF-kappaB-mediated iNOS gene expression and enzyme activity. | 2006-06 |
|
| Instrument dependence of electrospray ionization and tandem mass spectrometric fragmentation of the gingerols. | 2006 |
|
| 6-Gingerol prevents cisplatin-induced acute renal failure in rats. | 2006 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:43:34 GMT 2025
by
admin
on
Mon Mar 31 18:43:34 GMT 2025
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| Record UNII |
925QK2Z900
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| Record Status |
Validated (UNII)
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| Record Version |
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DSLD |
1626 (Number of products:14)
Created by
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| Code System | Code | Type | Description | ||
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442793
Created by
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GINGEROL
Created by
admin on Mon Mar 31 18:43:35 GMT 2025 , Edited by admin on Mon Mar 31 18:43:35 GMT 2025
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10136
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23513-14-6
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C007845
Created by
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PRIMARY | |||
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m5729
Created by
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PRIMARY | Merck Index | ||
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DTXSID3041035
Created by
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PRIMARY | |||
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925QK2Z900
Created by
admin on Mon Mar 31 18:43:35 GMT 2025 , Edited by admin on Mon Mar 31 18:43:35 GMT 2025
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PRIMARY |
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