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14901-07-6,MFCD00001549
Catalog No.:AA00393N

14901-07-6 | 4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00393N
Chemical Name:
4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one
CAS Number:
14901-07-6
Molecular Formula:
C13H20O
Molecular Weight:
192.2973
MDL Number:
MFCD00001549
SMILES:
CC(=O)C=CC1=C(C)CCCC1(C)C
FEMA Number:
2595
Properties
Computed Properties
 
Complexity:
292  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
2.9  

Literature

Title: Functional Characterization of the Odorant Receptor 51E2 in Human Melanocytes.

Journal: The Journal of biological chemistry 20160819

Title: Apoptosis initiation of β-ionone in SGC-7901 gastric carcinoma cancer cells via a PI3K-AKT pathway.

Journal: Archives of toxicology 20130301

Title: β-Ionone attenuates LPS-induced pro-inflammatory mediators such as NO, PGE2 and TNF-α in BV2 microglial cells via suppression of the NF-κB and MAPK pathway.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20130301

Title: Synthesis of β-ionone derived chalcones as potent antimicrobial agents.

Journal: Bioorganic & medicinal chemistry letters 20121015

Title: Mislocalized opsin and cAMP signaling: a mechanism for sprouting by rod cells in retinal degeneration.

Journal: Investigative ophthalmology & visual science 20120901

Title: Synergistic effects of the combination of β-ionone and sorafenib on metastasis of human hepatoma SK-Hep-1 cells.

Journal: Investigational new drugs 20120801

Title: CYP264B1 from Sorangium cellulosum So ce56: a fascinating norisoprenoid and sesquiterpene hydroxylase.

Journal: Applied microbiology and biotechnology 20120701

Title: Chemical composition and in vitro cytotoxic, genotoxic effects of essential oil from Urtica dioica L.

Journal: Bulletin of environmental contamination and toxicology 20120501

Title: Antiproliferative and antioxidant potential of beta-ionone against benzo(a)pyrene-induced lung carcinogenesis in Swiss albino mice.

Journal: Molecular and cellular biochemistry 20120401

Title: The anti-metastatic efficacy of β-ionone and the possible mechanisms of action in human hepatocarcinoma SK-Hep-1 cells.

Journal: The British journal of nutrition 20120301

Title: Function and immunocytochemical localization of two novel odorant-binding proteins in olfactory sensilla of the scarab beetle Holotrichia oblita Faldermann (Coleoptera: Scarabaeidae).

Journal: Chemical senses 20120201

Title: Microwave-assisted purge-and-trap extraction device coupled with gas chromatography and mass spectrometry for the determination of five predominant odors in sediment, fish tissues, and algal cells.

Journal: Journal of chromatography. A 20120106

Title: Aroma evaluation of gamazumi (Viburnum dilatatum) by aroma extract dilution analysis and odour activity value.

Journal: Phytochemical analysis : PCA 20120101

Title: Biosynthesis of α- and β-ionone, prominent scent compounds, in flowers of Osmanthus fragrans.

Journal: Acta biochimica Polonica 20120101

Title: Enhanced β-ionone emission in Arabidopsis over-expressing AtCCD1 reduces feeding damage in vivo by the crucifer flea beetle.

Journal: Environmental entomology 20111201

Title: Elucidating the toxicity targets of β-ionone on photosynthetic system of Microcystis aeruginosa NIES-843 (Cyanobacteria).

Journal: Aquatic toxicology (Amsterdam, Netherlands) 20110701

Title: Simultaneous determination of eight common odors in natural water body using automatic purge and trap coupled to gas chromatography with mass spectrometry.

Journal: Journal of chromatography. A 20110617

Title: Structural characteristics around the β-ionone ring of the retinal chromophore in Salinibacter sensory rhodopsin I.

Journal: Biochemistry 20110607

Title: Efficacy of geraniol but not of β-ionone or their combination for the chemoprevention of rat colon carcinogenesis.

Journal: Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20110601

Title: Chemopreventive effects of β-ionone and geraniol during rat hepatocarcinogenesis promotion: distinct actions on cell proliferation, apoptosis, HMGCoA reductase, and RhoA.

Journal: The Journal of nutritional biochemistry 20110201

Title: Structural Analysis of CYP101C1 from Novosphingobium aromaticivorans DSM12444.

Journal: Chembiochem : a European journal of chemical biology 20110103

Title: A systematic study on spatial and seasonal patterns of eight taste and odor compounds with relation to various biotic and abiotic parameters in Gonghu Bay of Lake Taihu, China.

Journal: The Science of the total environment 20101215

Title: QM/MM study of dehydro and dihydro β-ionone retinal analogues in squid and bovine rhodopsins: implications for vision in salamander rhodopsin.

Journal: Journal of the American Chemical Society 20101117

Title: Binding of more than one retinoid to visual opsins.

Journal: Biophysical journal 20101006

Title: Carotenoid content impacts flavor acceptability in tomato (Solanum lycopersicum).

Journal: Journal of the science of food and agriculture 20101001

Title: beta-Ionone-induced apoptosis in human osteosarcoma (U2os) cells occurs via a p53-dependent signaling pathway.

Journal: Molecular biology reports 20100701

Title: Allelopathy and allelopathic substance in the moss Rhynchostegium pallidifolium.

Journal: Journal of plant physiology 20100415

Title: beta-Ionone enhances TRAIL-induced apoptosis in hepatocellular carcinoma cells through Sp1-dependent upregulation of DR5 and downregulation of NF-kappaB activity.

Journal: Molecular cancer therapeutics 20100401

Title: A cytochrome P450 class I electron transfer system from Novosphingobium aromaticivorans.

Journal: Applied microbiology and biotechnology 20100301

Title: Effects of beta-ionone on mammary carcinogenesis and antioxidant status in rats treated with DMBA.

Journal: Nutrition and cancer 20100101

Title: Design and synthesis of androgen receptor antagonists with bulky side chains for overcoming antiandrogen resistance.

Journal: Journal of medicinal chemistry 20090910

Title: Online gas chromatography combustion/pyrolysis-isotope ratio mass spectrometry (HRGC-C/P-IRMS) of (+/-)-Dihydroactinidiolide from tea ( Camellia sinensis ) and rooibos tea ( Aspalathus linearis ).

Journal: Journal of agricultural and food chemistry 20090708

Title: Activation of an olfactory receptor inhibits proliferation of prostate cancer cells.

Journal: The Journal of biological chemistry 20090612

Title: Occurrence of dissolved and particle-bound taste and odor compounds in Swiss lake waters.

Journal: Water research 20090501

Title: Substrate specificity of a recombinant chicken beta-carotene 15,15'-monooxygenase that converts beta-carotene into retinal.

Journal: Biotechnology letters 20090301

Title: Changes in some carotenoids and apocarotenoids during flower development in Boronia megastigma (Nees).

Journal: Journal of agricultural and food chemistry 20090225

Title: Beta-ionone activates and bleaches visual pigment in salamander photoreceptors.

Journal: Visual neuroscience 20090101

Title: A high-throughput screening method for small-molecule pharmacologic chaperones of misfolded rhodopsin.

Journal: Investigative ophthalmology & visual science 20080701

Title: beta-Ionone suppresses mammary carcinogenesis, proliferative activity and induces apoptosis in the mammary gland of the Sprague-Dawley rat.

Journal: International journal of cancer 20080615

Title: Lysis of cyanobacteria with volatile organic compounds.

Journal: Chemosphere 20080401

Title: Improved co-oxidation of beta-carotene to beta-ionone using xanthine oxidase-generated reactive oxygen species in a multiphasic system.

Journal: Biotechnology journal 20080201

Title: Beta-ionone inhibits colonic aberrant crypt foci formation in rats, suppresses cell growth, and induces retinoid X receptor-alpha in human colon cancer cells.

Journal: Molecular cancer therapeutics 20080101

Title: [Beta-ionone induced apoptosis in SGC-7901 cells].

Journal: Wei sheng yan jiu = Journal of hygiene research 20071101

Title: alpha-Tocopherol increases caspase-3 up-regulation and apoptosis by beta-carotene cleavage products in human neutrophils.

Journal: Biochimica et biophysica acta 20070901

Title: Flavor authentication studies of alpha-ionone, beta-ionone, and alpha-ionol from various sources.

Journal: Journal of agricultural and food chemistry 20070808

Title: 4-pyridyl carbonyl and related compounds as thrips lures: effectiveness for onion thrips and new zealand flower thrips in field experiments.

Journal: Journal of agricultural and food chemistry 20070725

Title: Batch and continuous culture kinetics for production of carotenoids by beta-ionone-resistant mutant of Xanthophyllomyces dendrorhous.

Journal: Journal of microbiology and biotechnology 20070701

Title: Light-induced changes in an aqueous beta-carotene system stored under halogen and fluorescent lamps, affected by two oxygen partial pressures.

Journal: Journal of agricultural and food chemistry 20070627

Title: The role of the beta-ionone ring in the photochemical reaction of rhodopsin.

Journal: The journal of physical chemistry. A 20070111

Title: Annual dynamics and origins of the odorous compounds in the pilot experimental area of Lake Dianchi, China.

Journal: Water science and technology : a journal of the International Association on Water Pollution Research 20070101

Title: Fragrance material review on beta-ionone.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20070101

Title: Fragrance material review on ionone.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20070101

Title: Synthesis and preliminary biological evaluation of beta-carotene and retinoic acid oxidation products.

Journal: Bioorganic & medicinal chemistry 20061201

Title: Novel method for aroma recovery from the bioconversion of lutein to beta-ionone by Trichosporon asahii using a mesoporous silicate material.

Journal: Applied microbiology and biotechnology 20060701

Title: Study on the mutagenicity and antimutagenicity of beta-ionone in the Salmonella/microsome assay.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20060401

Title: Biotransformation of beta-ionone by engineered cytochrome P450 BM-3.

Journal: Applied microbiology and biotechnology 20060301

Title: Differences in the pharmacological activation of visual opsins.

Journal: Visual neuroscience 20060101

Title: [Effect of beta-ionone in human mammary cancer cells (Er-) by MAPK pathway].

Journal: Wei sheng yan jiu = Journal of hygiene research 20051101

Title: Efficient terpene hydroxylation catalysts based upon P450 enzymes derived from actinomycetes.

Journal: Organic & biomolecular chemistry 20050821

Title: Chemical defenses of Trifolium glanduliferum against redlegged earth mite Halotydeus destructor.

Journal: Journal of agricultural and food chemistry 20050810

Title: Structure, spectroscopy, and spectral tuning of the gas-phase retinal chromophore: the beta-ionone 'handle' and alkyl group effect.

Journal: The journal of physical chemistry. A 20050728

Title: Electrospray tandem mass spectrometric analysis of zeaxanthin and its oxidation products.

Journal: Journal of mass spectrometry : JMS 20050701

Title: [Inhibitory effect of potential metastasis in SGC-7901 cells induced by beta-ionone].

Journal: Wei sheng yan jiu = Journal of hygiene research 20050701

Title: Geranylgeraniol and beta-ionone inhibit hepatic preneoplastic lesions, cell proliferation, total plasma cholesterol and DNA damage during the initial phases of hepatocarcinogenesis, but only the former inhibits NF-kappaB activation.

Journal: Carcinogenesis 20050601

Title: Comprehensive authentication of (E)-alpha(beta)-ionone from raspberries, using constant flow MDGC-C/P-IRMS and enantio-MDGC-MS.

Journal: Journal of agricultural and food chemistry 20050223

Title: The tomato carotenoid cleavage dioxygenase 1 genes contribute to the formation of the flavor volatiles beta-ionone, pseudoionone, and geranylacetone.

Journal: The Plant journal : for cell and molecular biology 20041201

Title: Geraniol and beta-ionone inhibit proliferation, cell cycle progression, and cyclin-dependent kinase 2 activity in MCF-7 breast cancer cells independent of effects on HMG-CoA reductase activity.

Journal: Biochemical pharmacology 20041101

Title: Circadian regulation of the PhCCD1 carotenoid cleavage dioxygenase controls emission of beta-ionone, a fragrance volatile of petunia flowers.

Journal: Plant physiology 20041101

Title: The ring of the rhodopsin chromophore in a hydrophobic activation switch within the binding pocket.

Journal: Journal of molecular biology 20041022

Title: [Inhibitory effect on mammary carcinoma cells induced by beta-ionone].

Journal: Wei sheng yan jiu = Journal of hygiene research 20040301

Title: Apoptosis of human gastric adenocarcinoma cells induced by beta-ionone.

Journal: World journal of gastroenterology 20040201

Title: Inhibition of beta-ionone on SGC-7901 cell proliferation and upregulation of metalloproteinases-1 and -2 expression.

Journal: World journal of gastroenterology 20040115

Title: Conformational similarities in the beta-ionone ring region of the rhodopsin chromophore in its ground state and after photoactivation to the metarhodopsin-I intermediate.

Journal: Biochemistry 20031125

Title: Production of tobacco aroma from lutein. Specific role of the microorganisms involved in the process.

Journal: Applied microbiology and biotechnology 20031001

Title: Cleavage of beta,beta-carotene to flavor compounds by fungi.

Journal: Applied microbiology and biotechnology 20030901

Title: Expression of CYP2A3 mRNA and its regulation by 3-methylcholanthrene, pyrazole, and beta-ionone in rat tissues.

Journal: Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20030701

Title: A peroxidase from Lepista irina cleaves beta,beta-carotene to flavor compounds.

Journal: Biological chemistry 20030701

Title: Enzymatic carotenoid cleavage in star fruit (Averrhoa carambola).

Journal: Phytochemistry 20030501

Title: Effect of cis/trans isomerism of beta-carotene on the ratios of volatile compounds produced during oxidative degradation.

Journal: Journal of agricultural and food chemistry 20030326

Title: Investigation of binding behavior of alpha- and beta-ionones to beta-lactoglobulin at different pH values using a diffusion-based NOE pumping technique.

Journal: Journal of agricultural and food chemistry 20030326

Title: Inhibition of cyclophosphamide-induced teratogenesis by beta-ionone.

Journal: Toxicology letters 20030303

Title: Modelling of photointermediates suggests a mechanism of the flip of the beta-ionone moiety of the retinylidene chromophore in the rhodopsin photocascade.

Journal: Chembiochem : a European journal of chemical biology 20030303

Title: Differential effects of tomato (Lycopersicon esculentum mill) matrix on the volatility of important aroma compounds.

Journal: Journal of agricultural and food chemistry 20030129

Title: 11-cis-retinal protonated Schiff base: influence of the protein environment on the geometry of the rhodopsin chromophore.

Journal: Biochemistry 20021224

Title: Nuclear magnetic resonance spectroscopic study of beta-lactoglobulin interactions with two flavor compounds, gamma-decalactone and beta-ionone.

Journal: Journal of agricultural and food chemistry 20021120

Title: Determination of volatile compounds in Grenache wines in relation with different terroirs in the Rhone Valley.

Journal: Journal of agricultural and food chemistry 20021023

Title: Beta-carotene cleavage products induce oxidative stress in vitro by impairing mitochondrial respiration.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20020801

Title: Effect of storage on some volatile aroma compounds in fresh-cut cantaloupe melon.

Journal: Journal of agricultural and food chemistry 20020703

Title: Relative orientation between the beta-ionone ring and the polyene chain for the chromophore of rhodopsin in native membranes.

Journal: Biochemistry 20020618

Title: Improved hardware and software for quick gas chromatography-olfactometry using CHARM and GC-'SNIF' analysis.

Journal: Analytical chemistry 20020515

Title: Induction of cytochrome P450 1A and 2B by alpha- and beta-ionone in Sprague Dawley rats.

Journal: Archives of pharmacal research 20020401

Title: Fullerene modified supported lipid membrane as sensitive element of sensor for odorants.

Journal: Biosensors & bioelectronics 20011201

Title: Identification and characterization of a mammalian enzyme catalyzing the asymmetric oxidative cleavage of provitamin A.

Journal: The Journal of biological chemistry 20010427

Title: Apoptosis and cell-cycle arrest in human and murine tumor cells are initiated by isoprenoids.

Journal: The Journal of nutrition 19990401

Title: Antifungal properties of essential oils and their main components upon Cryptococcus neoformans.

Journal: Mycopathologia 19941201

Title: Mahsa Ansari, et al. β-Ionone and Its Analogs as Promising Anticancer Agents. Eur J Med Chem. 2016 Nov 10;123:141-154.

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SDS
Tags:14901-07-6 Molecular Formula|14901-07-6 MDL|14901-07-6 SMILES|14901-07-6 4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one