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555-66-8,MFCD01736094
Catalog No.:AA0035VJ

555-66-8 | Shogaol

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1mg
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5mg
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50mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0035VJ
Chemical Name:
Shogaol
CAS Number:
555-66-8
Molecular Formula:
C17H24O3
Molecular Weight:
276.3707
MDL Number:
MFCD01736094
SMILES:
CCCCC/C=C/C(=O)CCc1ccc(c(c1)OC)O
NSC Number:
752389
Properties
Properties
 
BP:
427.5±35.0℃ at 760 Torr   
Form:
Solid  
Storage:
Light sensitive;Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
299  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
9  
XLogP3:
3.7  

Literature

Title: The hidden mechanism beyond ginger (Zingiber officinale Rosc.) potent in vivo and in vitro anti-inflammatory activity.

Journal: Journal of ethnopharmacology 20180325

Title: 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: Journal of Crohn's & colitis 20180101

Title: 6-Shogaol ameliorates diabetic nephropathy through anti-inflammatory, hyperlipidemic, anti-oxidative activity in db/db mice.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20180101

Title: 6-Shogaol attenuates LPS-induced inflammation in BV2 microglia cells by activating PPAR-γ.

Journal: Oncotarget 20170627

Title: [6]-gingerol and [6]-shogaol, active ingredients of the traditional Japanese medicine hangeshashinto, relief oral ulcerative mucositis-induced pain via action on Na(+) channels.

Journal: Pharmacological research 20170301

Title: Revealing the effect of 6-gingerol, 6-shogaol and curcumin on mPGES-1, GSK-3β and β-catenin pathway in A549 cell line.

Journal: Chemico-biological interactions 20161025

Title: 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.

Journal: Chemico-biological interactions 20150225

Title: Ginger compound [6]-shogaol and its cysteine-conjugated metabolite (M2) activate Nrf2 in colon epithelial cells in vitro and in vivo.

Journal: Chemical research in toxicology 20140915

Title: A novel shogaol analog suppresses cancer cell invasion and inflammation, and displays cytoprotective effects through modulation of NF-κB and Nrf2-Keap1 signaling pathways.

Journal: Toxicology and applied pharmacology 20131101

Title: In vitro antioxidant and anti-inflammatory activities of 1-dehydro-[6]-gingerdione, 6-shogaol, 6-dehydroshogaol and hexahydrocurcumin.

Journal: Food chemistry 20121115

Title: Enhanced CD36 expression changes the role of Nrf2 activation from anti-atherogenic to pro-atherogenic in apoE-deficient mice.

Journal: Atherosclerosis 20121101

Title: Identification of phase II metabolites of thiol-conjugated [6]-shogaol in mouse urine using high-performance liquid chromatography tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20121015

Title: 6-Shogaol, a ginger product, modulates neuroinflammation: a new approach to neuroprotection.

Journal: Neuropharmacology 20120801

Title: Molecular mechanism inhibiting human hepatocarcinoma cell invasion by 6-shogaol and 6-gingerol.

Journal: Molecular nutrition & food research 20120801

Title: 6-shogaol-rich extract from ginger up-regulates the antioxidant defense systems in cells and mice.

Journal: Molecules (Basel, Switzerland) 20120704

Title: Zingiber officinale extract exhibits antidiabetic potential via modulating glucose uptake, protein glycation and inhibiting adipocyte differentiation: an in vitro study.

Journal: Journal of the science of food and agriculture 20120701

Title: Effects of [6]-shogaol on cholinergic signaling in HT22 cells following neuronal damage induced by hydrogen peroxide.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120501

Title: Metabolism of [6]-shogaol in mice and in cancer cells.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20120401

Title: Cytotoxic, cytoprotective and antioxidant effects of isolated phenolic compounds from fresh ginger.

Journal: Fitoterapia 20120401

Title: Antiinflammatory effects of ginger and some of its components in human bronchial epithelial (BEAS-2B) cells.

Journal: Phytotherapy research : PTR 20120301

Title: Protection by [6]-shogaol against lipopolysaccharide-induced toxicity in murine astrocytes is related to production of brain-derived neurotrophic factor.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120301

Title: Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators.

Journal: Bioorganic & medicinal chemistry letters 20120215

Title: 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: Journal of agricultural and food chemistry 20120125

Title: Anti-inflammatory effects of [6]-shogaol: potential roles of HDAC inhibition and HSP70 induction.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20111101

Title: 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: Journal of medicinal chemistry 20110922

Title: Preparation of the monomers of gingerols and 6-shogaol by flash high speed counter-current chromatography.

Journal: Journal of chromatography. A 20110909

Title: Examination of the pharmacokinetics of active ingredients of ginger in humans.

Journal: The AAPS journal 20110901

Title: Shogaols at proapoptotic concentrations induce G(2)/M arrest and aberrant mitotic cell death associated with tubulin aggregation.

Journal: Apoptosis : an international journal on programmed cell death 20110801

Title: Effects of ginger constituents on the gastrointestinal tract: role of cholinergic M3 and serotonergic 5-HT3 and 5-HT4 receptors.

Journal: Planta medica 20110701

Title: Update on the chemopreventive effects of ginger and its phytochemicals.

Journal: Critical reviews in food science and nutrition 20110701

Title: Ginger suppresses phthalate ester-induced airway remodeling.

Journal: Journal of agricultural and food chemistry 20110413

Title: Quantitative analysis of ginger components in commercial products using liquid chromatography with electrochemical array detection.

Journal: Journal of agricultural and food chemistry 20101222

Title: Zingiber officinale (ginger) compounds have tetracycline-resistance modifying effects against clinical extensively drug-resistant Acinetobacter baumannii.

Journal: Phytotherapy research : PTR 20101201

Title: 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.

Journal: British journal of pharmacology 20101201

Title: Anti-invasion effects of 6-shogaol and 6-gingerol, two active components in ginger, on human hepatocarcinoma cells.

Journal: Molecular nutrition & food research 20101101

Title: Larvicidal constituents of Zingiber officinale (ginger) against Anisakis simplex.

Journal: Planta medica 20101101

Title: 6-Shogaol is more effective than 6-gingerol and curcumin in inhibiting 12-O-tetradecanoylphorbol 13-acetate-induced tumor promotion in mice.

Journal: Molecular nutrition & food research 20100901

Title: Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2).

Journal: Journal of natural products 20100827

Title: Pharmacokinetics of [6]-shogaol, a pungent ingredient of Zingiber officinale Roscoe (Part I).

Journal: Journal of natural medicines 20100701

Title: Identification of serotonin 5-HT1A receptor partial agonists in ginger.

Journal: Bioorganic & medicinal chemistry 20100501

Title: Induction of apoptosis by [8]-shogaol via reactive oxygen species generation, glutathione depletion, and caspase activation in human leukemia cells.

Journal: Journal of agricultural and food chemistry 20100324

Title: Comparative antioxidant and anti-inflammatory effects of [6]-gingerol, [8]-gingerol, [10]-gingerol and [6]-shogaol.

Journal: Journal of ethnopharmacology 20100203

Title: 6-Shogaol inhibits monosodium urate crystal-induced inflammation--an in vivo and in vitro study.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20100101

Title: Increased growth inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols from Zingiber officinale relative to gingerols.

Journal: Journal of agricultural and food chemistry 20091125

Title: 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: Journal of agricultural and food chemistry 20091028

Title: Six-shogaol inhibits production of tumour necrosis factor alpha, interleukin-1 beta and nitric oxide from lipopolysaccharide-stimulated RAW 264.7 macrophages.

Journal: The West Indian medical journal 20090901

Title: Compounds from Sichuan and Melegueta peppers activate, covalently and non-covalently, TRPA1 and TRPV1 channels.

Journal: British journal of pharmacology 20090801

Title: TBK1-targeted suppression of TRIF-dependent signaling pathway of Toll-like receptors by 6-shogaol, an active component of ginger.

Journal: Bioscience, biotechnology, and biochemistry 20090701

Title: Inhibition of homodimerization of toll-like receptor 4 by 6-shogaol.

Journal: Molecules and cells 20090227

Title: Modulation of macrophage functions by compounds isolated from Zingiber officinale.

Journal: Planta medica 20090201

Title: Characterization of novel furan compounds on the basis of their radical scavenging activity and cytoprotective effects against glutamate- and lipopolysaccharide-induced insults.

Journal: Bioorganic & medicinal chemistry 20081215

Title: 6-Shogaol suppressed lipopolysaccharide-induced up-expression of iNOS and COX-2 in murine macrophages.

Journal: Molecular nutrition & food research 20081201

Title: Specific reaction of alpha,beta-unsaturated carbonyl compounds such as 6-shogaol with sulfhydryl groups in tubulin leading to microtubule damage.

Journal: FEBS letters 20081015

Title: Muscarinic, Ca(++) antagonist and specific butyrylcholinesterase inhibitory activity of dried ginger extract might explain its use in dementia.

Journal: The Journal of pharmacy and pharmacology 20081001

Title: 6-Shogaol and 6-gingerol, the pungent of ginger, inhibit TNF-alpha mediated downregulation of adiponectin expression via different mechanisms in 3T3-L1 adipocytes.

Journal: Biochemical and biophysical research communications 20080829

Title: Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20080801

Title: Changes in the contents of oleoresin and pungent bioactive principles of Jamaican ginger (Zingiber officinale Roscoe.) during maturation.

Journal: Journal of agricultural and food chemistry 20080723

Title: 6-Shogaol induces apoptosis in human colorectal carcinoma cells via ROS production, caspase activation, and GADD 153 expression.

Journal: Molecular nutrition & food research 20080501

Title: [RP-HPLC fingerprint evaluating different ginger juice as processing material].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080501

Title: Cytotoxic components from the dried rhizomes of Zingiber officinale Roscoe.

Journal: Archives of pharmacal research 20080401

Title: Stability of [6]-gingerol and [6]-shogaol in simulated gastric and intestinal fluids.

Journal: Journal of pharmaceutical and biomedical analysis 20071130

Title: Ginger ingredients reduce viability of gastric cancer cells via distinct mechanisms.

Journal: Biochemical and biophysical research communications 20071012

Title: 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: Journal of agricultural and food chemistry 20070207

Title: Liquid chromatographic determination of 6-, 8-, 10-gingerol, and 6-shogaol in ginger (Zingiber officinale) as the raw herb and dried aqueous extract.

Journal: Journal of AOAC International 20070101

Title: 6-Shogaol, a natural product, reduces cell death and restores motor function in rat spinal cord injury.

Journal: The European journal of neuroscience 20060801

Title: 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.

Journal: European journal of pharmacology 20060113

Title: 6-Shogaol reduced chronic inflammatory response in the knees of rats treated with complete Freund's adjuvant.

Journal: BMC pharmacology 20060101

Title: A nonpungent component of steamed ginger--[10]-shogaol--increases adrenaline secretion via the activation of TRPV1.

Journal: Nutritional neuroscience 20060101

Title: Cardiovascular effects of ginger aqueous extract and its phenolic constituents are mediated through multiple pathways.

Journal: Vascular pharmacology 20051001

Title: Sesquiterpenes and flavonol glycosides from Zingiber aromaticum and their CYP3A4 and CYP2D6 inhibitory activities.

Journal: Journal of natural products 20040701

Title: Side-chain length is important for shogaols in protecting neuronal cells from beta-amyloid insult.

Journal: Bioorganic & medicinal chemistry letters 20040308

Title: Ginger (Zingiber officinale Roscoe) and the gingerols inhibit the growth of Cag A+ strains of Helicobacter pylori.

Journal: Anticancer research 20030101

Title: Component of Zingiber officinale that improves the enhancement of small intestinal transport.

Journal: Planta medica 20021001

Title: Shogaols from Zingiber officinale as promising antifouling agents.

Journal: Bioscience, biotechnology, and biochemistry 20020801

Title: Shogaols from Zingiber officinale protect IMR32 human neuroblastoma and normal human umbilical vein endothelial cells from beta-amyloid(25-35) insult.

Journal: Planta medica 20020401

Title: The herbal medicine Dai-kenchu-to and one of its active components [6]-shogaol increase intestinal blood flow in rats.

Journal: Life sciences 20020315

Title: Structure-antiemetic-activity of some diarylheptanoids and their analogues.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20020301

Title: The stability of gingerol and shogaol in aqueous solutions.

Journal: Journal of pharmaceutical sciences 20011001

Title: Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes.

Journal: Pest management science 20010301

Title: Semwal RB, et al. Gingerols and shogaols: Important nutraceutical principles from ginger. Phytochemistry. 2015 Sep;117:554-68.

Title: Peng F, et al. Cytotoxic, cytoprotective and antioxidant effects of isolated phenolic compounds from fresh ginger. Fitoterapia. 2012 Apr;83(3):568-85.

Title: Sang S, et al. Increased growth inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols from Zingiber officinale relative to gingerols. J Agric Food Chem. 2009 Nov 25;57(22):10645-50.

Title: Bak MJ, et al. 6-shogaol-rich extract from ginger up-regulated the antioxidant defense systems in cells and mice. Molecules. 2012 Jul 4;17(7):8037-55.

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