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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
Structure of GINGEROL

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

HIDE SMILES / InChI

Molecular Formula C17H26O4
Molecular Weight 294.3859
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
125.0 µM [IC50]
129.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Primary
PubMed

PubMed

TitleDatePubMed
Effective anti-platelet and COX-1 enzyme inhibitors from pungent constituents of ginger.
2003
Enhancement of insulin sensitivity in adipocytes by ginger.
2004
Antioxidant properties of gingerol related compounds from ginger.
2004
Suppression of the nuclear factor-kappaB activation pathway by spice-derived phytochemicals: reasoning for seasoning.
2004 Dec
Cardiovascular effects of ginger aqueous extract and its phenolic constituents are mediated through multiple pathways.
2005 Oct
Biological basis for the use of botanicals in osteoarthritis and rheumatoid arthritis: a review.
2005 Sep
[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
Microsomal hydroxylation and glucuronidation of [6]-gingerol.
2006 Nov 15
Determination of 6-gingerol in ginger (Zingiber officinale) using high-performance thin-layer chromatography.
2006 Oct
[6]-Gingerol induces cell cycle arrest and cell death of mutant p53-expressing pancreatic cancer cells.
2006 Oct 31
Effect of 6-gingerol on pro-inflammatory cytokine production and costimulatory molecule expression in murine peritoneal macrophages.
2007 Apr
TRP channels and pain.
2007 Aug
Evaluation of the topical anti-inflammatory activity of ginger dry extracts from solutions and plasters.
2007 Dec
In vitro and in vivo modulation of testosterone mediated alterations in apoptosis related proteins by [6]-gingerol.
2007 Dec
Induction of multiple antibiotic resistance in Bacteroides fragilis by benzene and benzene-derived active compounds of commonly used analgesics, antiseptics and cleaning agents.
2007 Dec
Ginger inhibits cell growth and modulates angiogenic factors in ovarian cancer cells.
2007 Dec 20
In vitro synthesis of curcuminoids by type III polyketide synthase from Oryza sativa.
2007 Dec 28
Indian herbal medicines: possible potent therapeutic agents for rheumatoid arthritis.
2007 Jul
Antioxidant actions of phenolic compounds found in dietary plants on low-density lipoprotein and erythrocytes in vitro.
2007 Jun
Chemopreventive anti-inflammatory activities of curcumin and other phytochemicals mediated by MAP kinase phosphatase-5 in prostate cells.
2007 Jun
[6]-Gingerol prevents UVB-induced ROS production and COX-2 expression in vitro and in vivo.
2007 May
Activation of TRPA1 channels by the fatty acid amide hydrolase inhibitor 3'-carbamoylbiphenyl-3-yl cyclohexylcarbamate (URB597).
2007 May
Cancer preventive properties of ginger: a brief review.
2007 May
Stability of [6]-gingerol and [6]-shogaol in simulated gastric and intestinal fluids.
2007 Nov 30
Ginger ingredients reduce viability of gastric cancer cells via distinct mechanisms.
2007 Oct 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 Sep 1
Liquid chromatographic determination of 6-, 8-, 10-gingerol, and 6-shogaol in ginger (Zingiber officinale) as the raw herb and dried aqueous extract.
2007 Sep-Oct
Systemic administration of [6]-gingerol, a pungent constituent of ginger, induces hypothermia in rats via an inhibitory effect on metabolic rate.
2008 Apr 14
Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects.
2008 Aug
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
Plasma pharmacokinetics and tissue distribution of [6]-gingerol in rats.
2008 Dec
6-Shogaol suppressed lipopolysaccharide-induced up-expression of iNOS and COX-2 in murine macrophages.
2008 Dec
[6]-gingerol induces Ca2+ mobilization in Madin-Darby canine kidney cells.
2008 Jan
Effects of spice constituents on P-glycoprotein-mediated transport and CYP3A4-mediated metabolism in vitro.
2008 Jul
Changes in the contents of oleoresin and pungent bioactive principles of Jamaican ginger (Zingiber officinale Roscoe.) during maturation.
2008 Jul 23
Analysis of anti-platelet aggregation components of Rhizoma Zingiberis using chicken thrombocyte extract and high performance liquid chromatography.
2008 Jul 5
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
[RP-HPLC fingerprint evaluating different ginger juice as processing material].
2008 May
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
Antibacterial activity of [10]-gingerol and [12]-gingerol isolated from ginger rhizome against periodontal bacteria.
2008 Nov
Muscarinic, Ca(++) antagonist and specific butyrylcholinesterase inhibitory activity of dried ginger extract might explain its use in dementia.
2008 Oct
Specific reaction of alpha,beta-unsaturated carbonyl compounds such as 6-shogaol with sulfhydryl groups in tubulin leading to microtubule damage.
2008 Oct 15
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
Patents

Sample Use Guides

In Vivo Use Guide
10 mg orally twice daily for 12 weeks.
Route of Administration: Oral
In Vitro Use Guide
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 Tue Oct 22 13:54:21 UTC 2019
Edited
by admin
on Tue Oct 22 13:54:21 UTC 2019
Record UNII
925QK2Z900
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GINGEROL
Common Name English
(6)-GINGEROL [MI]
Common Name English
3-DECANONE, 5-HYDROXY-1-(4-HYDROXY-3-METHOXYPHENYL)-, (S)-
Systematic Name English
6-GINGEROL (CONSTITUENT OF GINGER) [DSC]
Common Name English
(6)-GINGEROL
MI  
Common Name English
(5S)-5-HYDROXY-1-(4-HYDROXY-3-METHOXYPHENYL)-3-DECANONE
Systematic Name English
C17-H26-O4
Common Name English
(S)-5-HYDROXY-1-(4-HYDROXY-3-METHOXYPHENYL)-3-DECANONE
Systematic Name English
6-GINGEROL
Common Name English
Code System Code Type Description
PUBCHEM
442793
Created by admin on Tue Oct 22 13:54:21 UTC 2019 , Edited by admin on Tue Oct 22 13:54:21 UTC 2019
PRIMARY
WIKIPEDIA
GINGEROL
Created by admin on Tue Oct 22 13:54:21 UTC 2019 , Edited by admin on Tue Oct 22 13:54:21 UTC 2019
PRIMARY
CAS
23513-14-6
Created by admin on Tue Oct 22 13:54:21 UTC 2019 , Edited by admin on Tue Oct 22 13:54:21 UTC 2019
PRIMARY
MESH
C007845
Created by admin on Tue Oct 22 13:54:21 UTC 2019 , Edited by admin on Tue Oct 22 13:54:21 UTC 2019
PRIMARY
MERCK INDEX
M5729
Created by admin on Tue Oct 22 13:54:21 UTC 2019 , Edited by admin on Tue Oct 22 13:54:21 UTC 2019
PRIMARY Merck Index
EPA CompTox
23513-14-6
Created by admin on Tue Oct 22 13:54:21 UTC 2019 , Edited by admin on Tue Oct 22 13:54:21 UTC 2019
PRIMARY
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