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Shogaol

CAS No.:
555-66-8
Catalog Number:
AG0035YB
Molecular Formula:
C17H24O3
Molecular Weight:
276.3707
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$105
- +
5mg
99%
1 week
United States
$207
- +
10mg
99%
1 week
United States
$307
- +
25mg
99%
1 week
United States
$557
- +
Product Description
Catalog Number:
AG0035YB
Chemical Name:
Shogaol
CAS Number:
555-66-8
Molecular Formula:
C17H24O3
Molecular Weight:
276.3707
MDL Number:
MFCD01736094
IUPAC Name:
(E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
InChI:
InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+
InChI Key:
OQWKEEOHDMUXEO-BQYQJAHWSA-N
SMILES:
CCCCC/C=C/C(=O)CCc1ccc(c(c1)OC)O
UNII:
83DNB5FIRF
NSC Number:
752389
Properties
Complexity:
299  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
276.173g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
276.376g/mol
Monoisotopic Mass:
276.173g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
46.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.7  
Literature
Title Journal
The hidden mechanism beyond ginger (Zingiber officinale Rosc.) potent in vivo and in vitro anti-inflammatory activity. Journal of ethnopharmacology 20180325
Oral Delivery of Nanoparticles Loaded With Ginger Active Compound, 6-Shogaol, Attenuates Ulcerative Colitis and Promotes Wound Healing in a Murine Model of Ulcerative Colitis. Journal of Crohn's & colitis 20180101
6-Shogaol ameliorates diabetic nephropathy through anti-inflammatory, hyperlipidemic, anti-oxidative activity in db/db mice. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20180101
6-Shogaol attenuates LPS-induced inflammation in BV2 microglia cells by activating PPAR-γ. Oncotarget 20170627
[6]-gingerol and [6]-shogaol, active ingredients of the traditional Japanese medicine hangeshashinto, relief oral ulcerative mucositis-induced pain via action on Na(+) channels. Pharmacological research 20170301
Revealing the effect of 6-gingerol, 6-shogaol and curcumin on mPGES-1, GSK-3β and β-catenin pathway in A549 cell line. Chemico-biological interactions 20161025
6-Shogaol enhances renal carcinoma Caki cells to TRAIL-induced apoptosis through reactive oxygen species-mediated cytochrome c release and down-regulation of c-FLIP(L) expression. Chemico-biological interactions 20150225
Ginger compound [6]-shogaol and its cysteine-conjugated metabolite (M2) activate Nrf2 in colon epithelial cells in vitro and in vivo. Chemical research in toxicology 20140915
A novel shogaol analog suppresses cancer cell invasion and inflammation, and displays cytoprotective effects through modulation of NF-κB and Nrf2-Keap1 signaling pathways. Toxicology and applied pharmacology 20131101
In vitro antioxidant and anti-inflammatory activities of 1-dehydro-[6]-gingerdione, 6-shogaol, 6-dehydroshogaol and hexahydrocurcumin. Food chemistry 20121115
Enhanced CD36 expression changes the role of Nrf2 activation from anti-atherogenic to pro-atherogenic in apoE-deficient mice. Atherosclerosis 20121101
Identification of phase II metabolites of thiol-conjugated [6]-shogaol in mouse urine using high-performance liquid chromatography tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20121015
6-Shogaol, a ginger product, modulates neuroinflammation: a new approach to neuroprotection. Neuropharmacology 20120801
Molecular mechanism inhibiting human hepatocarcinoma cell invasion by 6-shogaol and 6-gingerol. Molecular nutrition & food research 20120801
6-shogaol-rich extract from ginger up-regulates the antioxidant defense systems in cells and mice. Molecules (Basel, Switzerland) 20120704
Zingiber officinale extract exhibits antidiabetic potential via modulating glucose uptake, protein glycation and inhibiting adipocyte differentiation: an in vitro study. Journal of the science of food and agriculture 20120701
Effects of [6]-shogaol on cholinergic signaling in HT22 cells following neuronal damage induced by hydrogen peroxide. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120501
Metabolism of [6]-shogaol in mice and in cancer cells. Drug metabolism and disposition: the biological fate of chemicals 20120401
Cytotoxic, cytoprotective and antioxidant effects of isolated phenolic compounds from fresh ginger. Fitoterapia 20120401
Antiinflammatory effects of ginger and some of its components in human bronchial epithelial (BEAS-2B) cells. Phytotherapy research : PTR 20120301
Protection by [6]-shogaol against lipopolysaccharide-induced toxicity in murine astrocytes is related to production of brain-derived neurotrophic factor. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120301
Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators. Bioorganic & medicinal chemistry letters 20120215
4-Shogaol, an active constituent of dietary ginger, inhibits metastasis of MDA-MB-231 human breast adenocarcinoma cells by decreasing the repression of NF-κB/Snail on RKIP. Journal of agricultural and food chemistry 20120125
Anti-inflammatory effects of [6]-shogaol: potential roles of HDAC inhibition and HSP70 induction. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20111101
Synthesis of a new [6]-gingerol analogue and its protective effect with respect to the development of metabolic syndrome in mice fed a high-fat diet. Journal of medicinal chemistry 20110922
Preparation of the monomers of gingerols and 6-shogaol by flash high speed counter-current chromatography. Journal of chromatography. A 20110909
Examination of the pharmacokinetics of active ingredients of ginger in humans. The AAPS journal 20110901
Shogaols at proapoptotic concentrations induce G(2)/M arrest and aberrant mitotic cell death associated with tubulin aggregation. Apoptosis : an international journal on programmed cell death 20110801
Effects of ginger constituents on the gastrointestinal tract: role of cholinergic M3 and serotonergic 5-HT3 and 5-HT4 receptors. Planta medica 20110701
Update on the chemopreventive effects of ginger and its phytochemicals. Critical reviews in food science and nutrition 20110701
Ginger suppresses phthalate ester-induced airway remodeling. Journal of agricultural and food chemistry 20110413
Quantitative analysis of ginger components in commercial products using liquid chromatography with electrochemical array detection. Journal of agricultural and food chemistry 20101222
Zingiber officinale (ginger) compounds have tetracycline-resistance modifying effects against clinical extensively drug-resistant Acinetobacter baumannii. Phytotherapy research : PTR 20101201
6-Shogaol, an active constituent of ginger, inhibits breast cancer cell invasion by reducing matrix metalloproteinase-9 expression via blockade of nuclear factor-κB activation. British journal of pharmacology 20101201
Anti-invasion effects of 6-shogaol and 6-gingerol, two active components in ginger, on human hepatocarcinoma cells. Molecular nutrition & food research 20101101
Larvicidal constituents of Zingiber officinale (ginger) against Anisakis simplex. Planta medica 20101101
6-Shogaol is more effective than 6-gingerol and curcumin in inhibiting 12-O-tetradecanoylphorbol 13-acetate-induced tumor promotion in mice. Molecular nutrition & food research 20100901
Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2). Journal of natural products 20100827
Pharmacokinetics of [6]-shogaol, a pungent ingredient of Zingiber officinale Roscoe (Part I). Journal of natural medicines 20100701
Identification of serotonin 5-HT1A receptor partial agonists in ginger. Bioorganic & medicinal chemistry 20100501
Induction of apoptosis by [8]-shogaol via reactive oxygen species generation, glutathione depletion, and caspase activation in human leukemia cells. Journal of agricultural and food chemistry 20100324
Comparative antioxidant and anti-inflammatory effects of [6]-gingerol, [8]-gingerol, [10]-gingerol and [6]-shogaol. Journal of ethnopharmacology 20100203
6-Shogaol inhibits monosodium urate crystal-induced inflammation--an in vivo and in vitro study. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20100101
Increased growth inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols from Zingiber officinale relative to gingerols. Journal of agricultural and food chemistry 20091125
6-Shogaol, an active constituent of dietary ginger, induces autophagy by inhibiting the AKT/mTOR pathway in human non-small cell lung cancer A549 cells. Journal of agricultural and food chemistry 20091028
Six-shogaol inhibits production of tumour necrosis factor alpha, interleukin-1 beta and nitric oxide from lipopolysaccharide-stimulated RAW 264.7 macrophages. The West Indian medical journal 20090901
Compounds from Sichuan and Melegueta peppers activate, covalently and non-covalently, TRPA1 and TRPV1 channels. British journal of pharmacology 20090801
TBK1-targeted suppression of TRIF-dependent signaling pathway of Toll-like receptors by 6-shogaol, an active component of ginger. Bioscience, biotechnology, and biochemistry 20090701
Inhibition of homodimerization of toll-like receptor 4 by 6-shogaol. Molecules and cells 20090227
Modulation of macrophage functions by compounds isolated from Zingiber officinale. Planta medica 20090201
Characterization of novel furan compounds on the basis of their radical scavenging activity and cytoprotective effects against glutamate- and lipopolysaccharide-induced insults. Bioorganic & medicinal chemistry 20081215
6-Shogaol suppressed lipopolysaccharide-induced up-expression of iNOS and COX-2 in murine macrophages. Molecular nutrition & food research 20081201
Specific reaction of alpha,beta-unsaturated carbonyl compounds such as 6-shogaol with sulfhydryl groups in tubulin leading to microtubule damage. FEBS letters 20081015
Muscarinic, Ca(++) antagonist and specific butyrylcholinesterase inhibitory activity of dried ginger extract might explain its use in dementia. The Journal of pharmacy and pharmacology 20081001
6-Shogaol and 6-gingerol, the pungent of ginger, inhibit TNF-alpha mediated downregulation of adiponectin expression via different mechanisms in 3T3-L1 adipocytes. Biochemical and biophysical research communications 20080829
Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20080801
Changes in the contents of oleoresin and pungent bioactive principles of Jamaican ginger (Zingiber officinale Roscoe.) during maturation. Journal of agricultural and food chemistry 20080723
6-Shogaol induces apoptosis in human colorectal carcinoma cells via ROS production, caspase activation, and GADD 153 expression. Molecular nutrition & food research 20080501
[RP-HPLC fingerprint evaluating different ginger juice as processing material]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080501
Cytotoxic components from the dried rhizomes of Zingiber officinale Roscoe. Archives of pharmacal research 20080401
Stability of [6]-gingerol and [6]-shogaol in simulated gastric and intestinal fluids. Journal of pharmaceutical and biomedical analysis 20071130
Ginger ingredients reduce viability of gastric cancer cells via distinct mechanisms. Biochemical and biophysical research communications 20071012
6-shogaol (alkanone from ginger) induces apoptotic cell death of human hepatoma p53 mutant Mahlavu subline via an oxidative stress-mediated caspase-dependent mechanism. Journal of agricultural and food chemistry 20070207
Liquid chromatographic determination of 6-, 8-, 10-gingerol, and 6-shogaol in ginger (Zingiber officinale) as the raw herb and dried aqueous extract. Journal of AOAC International 20070101
6-Shogaol, a natural product, reduces cell death and restores motor function in rat spinal cord injury. The European journal of neuroscience 20060801
Mode of action of gingerols and shogaols on 5-HT3 receptors: binding studies, cation uptake by the receptor channel and contraction of isolated guinea-pig ileum. European journal of pharmacology 20060113
6-Shogaol reduced chronic inflammatory response in the knees of rats treated with complete Freund's adjuvant. BMC pharmacology 20060101
A nonpungent component of steamed ginger--[10]-shogaol--increases adrenaline secretion via the activation of TRPV1. Nutritional neuroscience 20060101
Cardiovascular effects of ginger aqueous extract and its phenolic constituents are mediated through multiple pathways. Vascular pharmacology 20051001
Sesquiterpenes and flavonol glycosides from Zingiber aromaticum and their CYP3A4 and CYP2D6 inhibitory activities. Journal of natural products 20040701
Side-chain length is important for shogaols in protecting neuronal cells from beta-amyloid insult. Bioorganic & medicinal chemistry letters 20040308
Ginger (Zingiber officinale Roscoe) and the gingerols inhibit the growth of Cag A+ strains of Helicobacter pylori. Anticancer research 20030101
Component of Zingiber officinale that improves the enhancement of small intestinal transport. Planta medica 20021001
Shogaols from Zingiber officinale as promising antifouling agents. Bioscience, biotechnology, and biochemistry 20020801
Shogaols from Zingiber officinale protect IMR32 human neuroblastoma and normal human umbilical vein endothelial cells from beta-amyloid(25-35) insult. Planta medica 20020401
The herbal medicine Dai-kenchu-to and one of its active components [6]-shogaol increase intestinal blood flow in rats. Life sciences 20020315
Structure-antiemetic-activity of some diarylheptanoids and their analogues. Phytomedicine : international journal of phytotherapy and phytopharmacology 20020301
The stability of gingerol and shogaol in aqueous solutions. Journal of pharmaceutical sciences 20011001
Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes. Pest management science 20010301
Properties