Beta-ionone is a colorless to light yellow liquid with an odor of cedar wood. In very dilute alcoholic solution the odor resembles odor of violets. Used in perfumery.
颜色/状态：
Colorless to pale, straw-colored liquid
气味：
Warm woody, dry, and fruity odor
味道：
Woody, berry, floral, green and fruity
蒸汽压力：
0.054 mm Hg at 25 °C
稳定性/保质期：
Stable under recommended storage conditions.
自燃温度：
250 °C (482 °F)
分解：
When heated to decomposition it emits acrid smoke and fumes.
A 3 kg male rabbit was orally administered a total of 23 g beta-ionone for 7 days (approx. 1000 mg/kg bw/day). Urine was collected daily and for 4 days after the final dose. Allylic ring oxidation and ketone reduction yielded 3-oxo-ionone, 3-oxo-beta-ionol, dihydro-3-oxo-beta-ionol, and 3-hydroxy-beta-ionol, which were detected in the urine. Unchanged beta-ionone and the glucuronic acid conjugates of 3-oxo-beta-ionol and dihydro-3-oxo-beta-ionol were also detected.
/Researchers/ fed beta-ionone to three rabbits in daily increasing doses of 2-5 g with a total dose of about 30 g in one week. In another test, feeding continued for two weeks in daily doses of 4 g, which increased to 5 g towards the end. In this schedule, the dose was not administered on some days. Urine was collected from all animals and analyzed for the presence of metabolites. The metabolites identified included 3-oxo-beta-ionone, bionol, dihydro-beta-ionol, oxy-beta-ionol, oxy-dihydro-beta-ionol, and oxy-dihydro-beta-ionone. Tetrahydro derivatives and multiple unsaturated products formed by dehydrogenation were not seen. Two separate feeding tests conducted in the spring and in the fall showed that conversion products of beta-ionone which are hydrogenated to the -hydroxyl and -carbonyl groups were excreted in the spring but not in the fall.
IDENTIFICATION AND USE: Beta-ionone (BI) is a colorless to pale, straw-colored liquid. BI is of use, not only in perfumery, but also as a key intermediate in the synthesis of Vitamins A, E, and K. HUMAN EXPOSURE AND TOXICITY: At 1% BI produced no irritation or sensitization in patients. At 5% concentration, 2 patients showed questionable positive irritation reactions, but there was no sensitization. ANIMAL STUDIES: No evidence of sensitization was observed in guinea pigs. In rabbits application of neat beta-ionone produced very slight to well-defined erythema on the abraded and intact skin at 24 hr and well defined erythema at 72 hr. Very slight conjunctival irritation was observed in all three rabbits at 0, 1, 2, and 4 hr with neat BI. In 90 day feeding study in rats BI did not produce adverse effects. In development study in BI-treated pregnant rats compared to the untreated controls, the uterus weight, the ratio of resorptions per implantations and the percentage of resorptions per implantation per litter were substantially increased, and the ratio of live fetuses per implantations per litter was drastically decreased with 1000 mg/kg; with 250, 500 and 750 mg/kg, no effects were produced. BI exhibited no mutagenic activity in Salmonella typhimurium (strains TA98, TA100, TA1535 and TA1537) at concentrations up to approximately 180 ug/plate with and without metabolic activation. ECOTOXICITY STUDIES: Ultrastructural examination by transmission electron microscopy indicated that the thylakoids were distorted, and the thylakoid membrane stacks began to collapse when M. aeruginosa NIES-843 was exposed to BI at a concentration of 22.5 and 33.75 mg/L.
A possible role of metabolic activation by cytochrome P450 (P450) in thioacetamide-induced hepatotoxicity was investigated in male BALB/c mice. The mice were pretreated with the P450 inducer, beta-ionone, subcutaneously at 600 mg/kg, 72 and 48 hr prior to an intraperitoneal administration of either 100 or 200 mg/kg of thioacetamide. The elevated activities of serum alanine aminotransferase and serum aspartate aminotransferase by thioacetamide were greatly potentiated by the pretreatment with beta-ionone. Moreover, the potentiation of thioacetamide-induced hepatotoxicity was also observed in the histopathological examination of livers. The hepatic necrosis by thioacetamide was potentiated when mice were pretreated with beta-ionone. In liver microsomes, the activities of P450 2B-specific pentoxyresorufin O-depentylase and benzyloxyresorufin O-debenzylase were significantly induced by the treatment with beta-ionone. Beta-ionone also induced other P450-associated monooxygenases. Because the pretreatment with beta-ionone was not hepatotoxic at the dose inducing P450s. our present results suggest that beta-ionone may be a useful model inducer of P450 enzyme(s) in studying toxic mechanism of certain chemicals which require metabolic activation by P450s in mice.
Female ICR mice were treated with cocaine either alone or in combination with one of several cytochrome P450 (CYP) inducers, i.e. phenobarbital, beta-ionone, dexamethasone and beta-naphthoflavone. Cocaine-induced hepatotoxicity was first observed by pretreatment with phenobarbital, beta-ionone or dexamethasone in accordance with significant elevation of cocaine N-demethylation, the first step of cocaine bioactivation. The hepatic lesions occured in the periportal region (zone 1) by phenobarbital and beta-ionone and in the perivenular region (zone 3) by dexamethasone. The activities of the enzyme specific for CYP isozyme were determined to elucidate the effects of pretreatment with CYP inducers. Beta-naphthoflavone induced CYP1A and 2B but had no effects on hepatotoxicity by cocaine. On the other hand, beta-ionone enhanced hepatotoxicity without induction of CYP3A. Activities of cocaine N-demethylase correlated well with CYP2A (r=0.83) and CYP2B (r=0.81). Cocaine N-demethylation was inhibited particularly by addition of the CYP2A specific inhibitor, 8-methoxypsoralen. Moreover, pretreatment with 8-methoxypsoralen produced a marked inhibition of the hepatotoxicity induced by cocaine in phenobarbital-treated mice. These results suggest that cocaine-induced hepatotoxicity in female mice was mediated in part by CYP2A, participating in cocaine N-demethylation.
beta-Ionone demonstrates potent anticancer activity both in vitro and in vivo. We determined tumor incidence and the number of rats bearing tumors as well as cell proliferation and apoptosis in a rat mammary cancer model induced by 7, 12-dimethylbenz[a]anthracene (DMBA). Rats were fed an AIN-76A diet containing beta-ionone (0, 9, 18 or 36 mmol/kg), starting 2 weeks before DMBA administration and continuing for 24 weeks. A dose-dependent inhibition of mammary carcinogenesis by dietary beta-ionone was observed. Corresponding tumor incidence values were 82.1, 53.3, 25.9 and 10.0% (p < 0.01 or 0.05). Time to tumor appearance increased and tumor multiplicity decreased with increasing dietary beta-ionone. Histopathological and immunohistochemical evaluations of tumors were performed on the 64, 31, 15 and 3 tumors, respectively, identified in rats from the respective groups of 30. The proportions of adenocarcinomas, adenomas and benign masses were equally distributed in the latter group. In proportions within the other groups, the proportions of adenocarcinomas and benign masses decreased and increased with increasing dietary beta-ionone. Proliferating cell nuclear antigen (PCNA), cyclin D1 and Bcl-2 expression decreased, and Bax expression and nuclear fragmentation increased with increasing dietary beta-ionone. These results demonstrate the potent capacity of dietary beta-ionone to suppress DMBA-initiated mammary cancer in rats.
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.
(E)-ψ-紫罗兰酮 、 硫酸 、 水 在
disodium;carbonate 、 beta-紫罗酮 作用下，
以
二氯甲烷 为溶剂，
42.0 ℃
、2.67 kPa
条件下，
反应 0.17h，
以495 g of 97.0% pure β-ionone were obtained, corresponding to a yield of β-ionone of 83.3% of theory的产率得到beta-紫罗酮
Fe(0)-Mediated Synthesis of Tri- and Tetra-Substituted Olefins from Carbonyls: An Environmentally Friendly Alternative to Cr(II)
作者：J. R. Falck、Romain Bejot、Deb K. Barma、Anish Bandyopadhyay、Suju Joseph、Charles Mioskowski
DOI：10.1021/jo061445u
日期：2006.10.1
carbonyls by activated polyhalides. In many instances, Fe(0) was equivalent or superior to Cr(II). Notably, Fe(0), but not Cr(II), proved compatible with a wide range of functionality, inter alia, unprotected phenol, aryl nitro, carboxylic acid, and alkyl nitrile. A surprising reversal of stereoselectivity for aldehydes versus ketones was observed using both metals. The resultant α-halo-α,β-unsaturated or α
Highly chemoselective palladium-catalyzed conjugate reduction of .alpha.,.beta.-unsaturated carbonyl compounds with silicon hydrides and zinc chloride cocatalyst
作者：Ehud. Keinan、Noam. Greenspoon
DOI：10.1021/ja00283a029
日期：1986.11
experiments and 'H NMR studies, a catalytic cycle is postulated in which the first step involves reversible coordination of the palladium complex to the electron-deficient olefin and oxidative addition of silicon hydride to form a hydridopalladium olefin complex. Migratory insertion of hydride into the coordinated olefin produces an intermediate palladium enolate which, via reductive elimination, collapses back
由可溶性钯催化剂、氢化硅烷和氯化锌组成的三组分体系能够有效地共轭还原α、不饱和酮和醛。最佳条件组包括二苯基硅烷作为最有效的氢化物供体，任何可溶于 0 或 I1 氧化态的钯配合物，当它被膦配体稳定时，以及作为最佳路易斯酸助催化剂的 ZnCl。该反应对于范围广泛的不饱和酮和醛非常普遍，并且对于这些迈克尔受体具有高度选择性，因为在这些条件下α，-不饱和羧酸衍生物的还原非常缓慢。当双氘代二苯基硅烷用于还原不饱和酮时，氘在底物的受阻较少的面上立体选择性地引入，并在 8 位上以区域选择性的方式引入。相反，当在痕量 D2O 存在下进行还原时，氘掺入发生在 a 位。在掺入氘的实验和 1 H NMR 研究的基础上，假定催化循环，其中第一步涉及钯配合物与缺电子烯烃的可逆配位和氢化硅的氧化加成以形成氢化钯烯烃配合物。氢化物迁移插入配位的烯烃产生中间体烯醇钯，通过还原消除，它塌缩回 Pd(0) 络合物和甲硅烷基烯
Organo tin nucleophiles IV. Palladium catalyzed conjugate reduction with tin hydride
作者：Ehud Keinan、Pierre A Gleize
DOI：10.1016/s0040-4039(00)86866-5
日期：——
Highly chemoselective conjugatereduction of α,β-unsaturated carbonyl compounds is now possible by using tributyl tin hydride with Pd(PØ3)4; an optimization study puts forth the importance of added radical scavenger and proton source in these reductions.
AlCl<sub>3</sub>-Promoted Conjugate Reduction of α,β Unsaturated Carbonyl Compounds with 1,3-Dimethyl-2-phenylbenzimidazoline
作者：Hidenori Chikashita、Kazuyoshi Itoh
DOI：10.1246/bcsj.59.1747
日期：1986.6
substrates. The catalytic efficiency of Lewis acids was found to be proportional to the efficiency to form a complex with a carbonyl group. The reduction of 2-cinnamoylpyridine with 2-deuterated DMBI revealed that in the reduction product, a deuterium atom was located at the β-position with respect to the carbonyl group. On the other hand, the reduction of the same substrate with DMBI followed by quenching
acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(III) intermediates were involved
