| InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+ |
| PSQYTAPXSHCGMF-BQYQJAHWSA-N |
| CC(=O)\C=C\C1=C(C)CCCC1(C)C |
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antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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volatile oil component
Any plant metabolite that is found naturally as a component of a volatile oil.
(via ionone )
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via ionone )
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fragrance
A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.
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View more via ChEBI Ontology
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(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one
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(E)-β-Ionone
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NIST Chemistry WebBook
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(E)-beta-Ionone
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ChemIDplus
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β-E-Ionone
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NIST Chemistry WebBook
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β-Ionon
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ChEBI
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β-ionone
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UniProt
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beta-Ionone
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KEGG COMPOUND
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trans-β-Ionone
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NIST Chemistry WebBook
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trans-beta-Ionone
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ChemIDplus
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1909545
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Reaxys Registry Number
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Reaxys
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79-77-6
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CAS Registry Number
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ChemIDplus
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79-77-6
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CAS Registry Number
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NIST Chemistry WebBook
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Asokkumar S, Naveenkumar C, Raghunandhakumar S, Kamaraj S, Anandakumar P, Jagan S, Devaki T (2012)
Antiproliferative and antioxidant potential of beta-ionone against benzo(a)pyrene-induced lung carcinogenesis in Swiss albino mice.
Molecular and cellular biochemistry 363, 335-345 [PubMed:22187222]
[show Abstract]
Nowadays, in developing countries like India, incidence of lung cancer is increasing rapidly, and as a consequence it has become the most common cause of malignancy-associated death. This study is aimed to evaluate the therapeutic efficacy of beta-ionone (ION), a precursor for carotenoids against benzo(a)pyrene [B(a)P]-induced lung carcinogenesis. B(a)P (50 mg/kg body weight, orally twice a week for 4 successive weeks)-induced lung cancer in mice was assessed both in tissue and serum in terms of increase LPO and tissue marker enzymes, such as aryl hydrocarbon hydroxylase, γ-glutamyl transpeptidase, 5'-nucleotidase, and lactate dehydrogenase, and serum tumor markers such as carcinoembryonic antigen and neuron-specific enolase with concordant decrease in activities of tissue enzymic and non-enzymic antioxidants were observed on the treatment of ION (60 mg/kg body weight, orally twice a week for 16 weeks) significantly attenuated LPO and restored all cancer marker enzymes and antioxidants levels to near normal, which indicates the anticancer effect of ION. This was further confirmed by histological staining of argyrophilic nucleolar organizer region and histopathological analysis of lung tissue, immunohistochemical and immunoblot analysis of proliferating cell nuclear antigen. Overall findings suggested that the ION effectively ameliorated the lung carcinogenesis, which is attributed to the antiproliferative and antioxidant potential through free radical scavenging property. | Ogunwande IA, Jimoh R, Ajetunmobi AA, Avoseh NO, Flamini G (2012)
Essential oil composition of Ficus benjamina (Moraceae) and Irvingia barteri (Irvingiaceae).
Natural product communications 7, 1673-1675 [PubMed:23413580]
[show Abstract]
Essential oils obtained by hydrodistillation of leaves of two Nigerian species were analyzed for their constituents by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The leaf oil of Ficus benjamina L. (Moraceae), collected during the day, contained high contents of alpha-pinene (13.9%), abietadiene (9.7%), cis-alpha-bisabolene (8.2%) and germacrene-D-4-ol (8.4%), while the night sample was dominated by germacrene-D-4-ol (31.5%), 1,10-di-epi-cubenol (8.8%) and hexahydrofarnesylacetone (8.3%). This could be a possible indication of differences in emissions of volatiles by F. benjamina during the day and night. The main compounds of Irvingia barteri Hook. f. (Irvingiaceae) were beta-caryophyllene (17.0%), (E)-a-ionone (10.0%), geranial (7.6%), (E)-beta-ionone (6.6%) and beta-gurjunene (5.1%). | Lalko J, Lapczynski A, McGinty D, Bhatia S, Letizia CS, Api AM (2007)
Fragrance material review on trans-beta-ionone.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 45 Suppl 1, S248-50 [PubMed:18031901]
[show Abstract]
A toxicologic and dermatologic review of trans-beta-Ionone when used as a fragrance ingredient is presented. | Zorn H, Langhoff S, Scheibner M, Berger RG (2003)
Cleavage of beta,beta-carotene to flavor compounds by fungi.
Applied microbiology and biotechnology 62, 331-336 [PubMed:12719936]
[show Abstract]
More than 50 filamentous fungi and yeasts, known for de novo synthesis or biotransformation of mono-, sesqui-, tri-, or tetraterpenes, were screened for their ability to cleave beta,beta-carotene to flavor compounds. Ten strains discolored a beta,beta-carotene-containing growth agar, indicating efficient degradation of beta,beta-carotene. Dihydroactinidiolide was formed as the sole conversion product of beta,beta-carotene in submerged cultures of Ganoderma applanatum, Hypomyces odoratus, Kuehneromyces mutabilis, and Trametes suaveolens. When mycelium-free culture supernatants from five species were applied for the conversions, nearly complete degradation of beta,beta-carotene was observed after 12 h. Carotenoid-derived volatile products were detected in the media of Ischnoderma benzoinum, Marasmius scorodonius, and Trametes versicolor. beta-Ionone proved to be the main metabolite in each case, whereas beta-cyclocitral, dihydroactinidiolide, and 2-hydroxy-2,6,6-trimethylcyclohexanone were formed in minor quantities. Using a photometric bleaching test, the beta,beta-carotene cleaving enzyme activities of M. scorodonius were partially characterized. | Gomes-Carneiro MR, De-Oliveira AC, De-Carvalho RR, Araujo IB, Souza CA, Kuriyama SN, Paumgartten FJ (2003)
Inhibition of cyclophosphamide-induced teratogenesis by beta-ionone.
Toxicology letters 138, 205-213 [PubMed:12565197]
[show Abstract]
Beta-ionone (BI) is a degraded (C 13) sesquiterpene found in plant essential oils. It has been used in the synthesis of perfume chemicals and vitamin A. Recently, it was reported that BI is a rather potent in vitro inhibitor of CYP2B1-catalysed reactions in rat liver microsomes. The present study was performed to investigate whether inhibition of CYP2B1 reactions by BI could lead to an attenuation of cyclophosphamide (CP)-induced embryotoxicity in the rat. In a preliminary experiment, a dose-dependent prolongation of pentobarbital sleeping time in male and female Wistar rats suggested that BI inhibits CYP2B1 in vivo as well. In a second experiment, rats were treated by gavage with BI (0, 250, 500, 750 or 1000 mg/kg body wt) 45 min prior to a subcutaneous injection of either CP (7.5 mg/kg body wt) or its vehicle (saline) on day 11 of pregnancy. BI alone, at the highest dose tested, caused a high proportion of resorptions. Lower doses of BI, however, clearly attenuated CP-induced embryolethality and teratogenicity. These results seem to support the view that, as far as rats are concerned, CYP2B1 plays an important role in the conversion of CP into its embryolethal and teratogenic metabolites. |
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