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471-05-6,MFCD03700769
Catalog No.:AA00DBTA

471-05-6 | zerumbone

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5mg
≥95%
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$55.00   $38.00
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10mg
≥95%
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$88.00   $61.00
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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:
AA00DBTA
Chemical Name:
zerumbone
CAS Number:
471-05-6
Molecular Formula:
C15H22O
Molecular Weight:
218.3346
MDL Number:
MFCD03700769
SMILES:
CC1=CCC(C)(C)C=CC(=O)C(=CCC1)C
NSC Number:
698299
Properties
Properties
 
Form:
Solid  
MP:
62 - 64°C  
Storage:
2-8℃;Inert atmosphere;Light sensitive;  

Computed Properties
 
Complexity:
354  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
3  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
1  
XLogP3:
3.9  

Literature

Title: Effects of a new synthetic zerumbone pendant derivative (ZPD) on apoptosis induction and anti-migratory effects in human cervical cancer cells.

Journal: Chemico-biological interactions 20171225

Title: Zerumbone reduced the inflammatory response of acute lung injury in endotoxin-treated mice via Akt-NFκB pathway.

Journal: Chemico-biological interactions 20170601

Title: Elevated IL-1β expression induces invasiveness of triple negative breast cancer cells and is suppressed by zerumbone.

Journal: Chemico-biological interactions 20161025

Title: Lipid-lowering effects of zerumbone, a natural cyclic sesquiterpene of Zingiber zerumbet Smith, in high-fat diet-induced hyperlipidemic hamsters.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20140701

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Antiulcer principle from Zingiber montanum.

Journal: Journal of ethnopharmacology 20120507

Title: Zerumbone attenuates the severity of acute necrotizing pancreatitis and pancreatitis-induced hepatic injury.

Journal: Mediators of inflammation 20120101

Title: Ginger phytochemicals mitigate the obesogenic effects of a high-fat diet in mice: a proteomic and biomarker network analysis.

Journal: Molecular nutrition & food research 20110901

Title: A short-chain dehydrogenase involved in terpene metabolism from Zingiber zerumbet.

Journal: The FEBS journal 20110801

Title: Liquid chromatography-tandem mass spectroscopic method for the determination of zerumbone in human plasma and its application to pharmacokinetics.

Journal: Journal of mass spectrometry : JMS 20110801

Title: Zerumbone induces heme oxygenase-1 expression in mouse skin and cultured murine epidermal cells through activation of Nrf2.

Journal: Cancer prevention research (Philadelphia, Pa.) 20110601

Title: Altered cross-linking of HSP27 by zerumbone as a novel strategy for overcoming HSP27-mediated radioresistance.

Journal: International journal of radiation oncology, biology, physics 20110315

Title: Zingiber zerumbet CYP71BA1 catalyzes the conversion of α-humulene to 8-hydroxy-α-humulene in zerumbone biosynthesis.

Journal: Cellular and molecular life sciences : CMLS 20110301

Title: Zerumbone-induced antinociception: involvement of the L-arginine-nitric oxide-cGMP -PKC-K+ ATP channel pathways.

Journal: Basic & clinical pharmacology & toxicology 20110301

Title: Zerumbone induces apoptosis in T-acute lymphoblastic leukemia cells.

Journal: Leukemia research 20110201

Title: Dietary zerumbone prevents against ultraviolet B-induced cataractogenesis in the mouse.

Journal: Molecular vision 20110101

Title: Dietary zerumbone prevents mouse cornea from UVB-induced photokeratitis through inhibition of NF-κB, iNOS, and TNF-α expression and reduction of MDA accumulation.

Journal: Molecular vision 20110101

Title: Effects of selected food phytochemicals in reducing the toxic actions of TCDD and p,p'-DDT in U937 macrophages.

Journal: Archives of toxicology 20101201

Title: Regression of cervical intraepithelial neoplasia by zerumbone in female Balb/c mice prenatally exposed to diethylstilboestrol: involvement of mitochondria-regulated apoptosis.

Journal: Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 20100901

Title: Potential chemoprevention of diethylnitrosamine-initiated and 2-acetylaminofluorene-promoted hepatocarcinogenesis by zerumbone from the rhizomes of the subtropical ginger (Zingiber zerumbet).

Journal: Chemico-biological interactions 20100805

Title: Zerumbone enhances TRAIL-induced apoptosis through the induction of death receptors in human colon cancer cells: Evidence for an essential role of reactive oxygen species.

Journal: Cancer research 20090815

Title: Combination of zerumbone and cisplatin to treat cervical intraepithelial neoplasia in female BALB/c mice.

Journal: International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20090801

Title: Preliminary analysis of the antinociceptive activity of zerumbone.

Journal: Fitoterapia 20090601

Title: In vitro ultramorphological assessment of apoptosis induced by zerumbone on (HeLa).

Journal: Journal of biomedicine & biotechnology 20090101

Title: Chemoprevention with phytochemicals targeting inducible nitric oxide synthase.

Journal: Forum of nutrition 20090101

Title: Zerumbone down-regulates chemokine receptor CXCR4 expression leading to inhibition of CXCL12-induced invasion of breast and pancreatic tumor cells.

Journal: Cancer research 20081101

Title: Molecular cloning and functional characterization of alpha-humulene synthase, a possible key enzyme of zerumbone biosynthesis in shampoo ginger (Zingiber zerumbet Smith).

Journal: Planta 20080501

Title: Targeting NOX, INOS and COX-2 in inflammatory cells: chemoprevention using food phytochemicals.

Journal: International journal of cancer 20071201

Title: Zerumbone exerts a beneficial effect on inflammatory parameters of cholecystokinin octapeptide-induced experimental pancreatitis but fails to improve histology.

Journal: Pancreas 20071001

Title: Zerumbone suppresses phorbol ester-induced expression of multiple scavenger receptor genes in THP-1 human monocytic cells.

Journal: Bioscience, biotechnology, and biochemistry 20070401

Title: Synthesis of a novel inhibitor against MRSA and VRE: preparation from zerumbone ring opening material showing histidine-kinase inhibition.

Journal: Bioorganic & medicinal chemistry letters 20070215

Title: Citrus nobiletin suppresses bone loss in ovariectomized ddY mice and collagen-induced arthritis in DBA/1J mice: possible involvement of receptor activator of NF-kappaB ligand (RANKL)-induced osteoclastogenesis regulation.

Journal: BioFactors (Oxford, England) 20070101

Title: Zerumbone abolishes NF-kappaB and IkappaBalpha kinase activation leading to suppression of antiapoptotic and metastatic gene expression, upregulation of apoptosis, and downregulation of invasion.

Journal: Oncogene 20051020

Title: Inhibitory actions of several natural products on proliferation of rat vascular smooth muscle cells induced by Hsp60 from Chlamydia pneumoniae J138.

Journal: Journal of agricultural and food chemistry 20041006

Title: Zerumbone, a tropical ginger sesquiterpene, activates phase II drug metabolizing enzymes.

Journal: FEBS letters 20040813

Title: Zerumbone, a sesquiterpene in subtropical ginger, suppresses skin tumor initiation and promotion stages in ICR mice.

Journal: International journal of cancer 20040701

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

Journal: Journal of natural products 20040701

Title: Suppression of dextran sodium sulfate-induced colitis in mice by zerumbone, a subtropical ginger sesquiterpene, and nimesulide: separately and in combination.

Journal: Biochemical pharmacology 20031001

Title: Effects of selected food factors with chemopreventive properties on combined lipopolysaccharide- and interferon-gamma-induced IkappaB degradation in RAW264.7 macrophages.

Journal: Cancer letters 20030530

Title: Antitumor activity of extract of Zingiber aromaticum and its bioactive sesquiterpenoid zerumbone.

Journal: Nutrition and cancer 20030101

Title: Redox-regulated mechanism may account for zerumbone's ability to suppress cancer-cell proliferation.

Journal: Carcinogenesis 20021101

Title: Zerumbone, a Southeast Asian ginger sesquiterpene, markedly suppresses free radical generation, proinflammatory protein production, and cancer cell proliferation accompanied by apoptosis: the alpha,beta-unsaturated carbonyl group is a prerequisite.

Journal: Carcinogenesis 20020501

Title: Chemoprevention of azoxymethane-induced rat aberrant crypt foci by dietary zerumbone isolated from Zingiber zerumbet.

Journal: Life sciences 20010907

Title: Murakami A, et al. Identification of zerumbone in Zingiber zerumbet Smith as a potent inhibitor of 12-O-tetradecanoylphorbol-13-acetate-induced Epstein-Barr virus activation. Biosci Biotechnol Biochem. 1999 Oct;63(10):1811-2.

Title: Kalantari K, et al. A Review of the Biomedical Applications of Zerumbone and the Techniques for Its Extractionfrom Ginger Rhizomes. Molecules. 2017 Sep 30;22(10).

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