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Homodimerization and crossed-dimerization reactions for ferulic acid and related compounds in an acidic ethanol solution were investigated via a formal [3 + 2] cycloaddition reaction. Arylindanes, as the major products, were produced from some of the acids with hydroxy group and/or methoxy groups at the para and meta positions of the phenyl ring. The formation of arylindane required the following consecutive reactions: (I) protonation of the first produced ester to afford to a benzylic cation, (II) which reacts with another ester to afford a new benzylic cation, and (III) followed by cyclization to produce the dimer. It is suggested that the para-substituent promoted both step I and step II and the meta-substituent accelerated step III. To rationalize the selectivity of homodimerization, the stability of the benzyl cations and the specific electron distribution on the molecular surface of each ester is discussed based on the results of the molecular orbital calculations.

Proanthocyanidins (PAs) contribute to the quality factors and health benefits of several Rosaceae fruits. Ume, also known as Japanese apricot (Prunus mume Sieb. Et. Zucc), is one of the most popular fruit trees grown in Japan, and its processed products are employed as a folk remedy in eastern Asian countries. However, the information available regarding the PAs present in the fruit remains limited. In this study, we analyzed the PAs and phenolic acid derivatives present in the fruit of ‘Nnanko,’ the most common cultivar, and found that the flesh tissue of the mature fruit contained levels of PAs similar to those of the hydroxycinnamic acids. The concentration of PAs in the endocarp tissue of the mature fruit was approximately 14 times higher than that of the flesh tissue. We also estimated the chemical structures of the PAs from the flesh and the endocarp by HPLC-ESI-MS/MS. Although 13 kinds of PAs, including 2 monomers, 4 B-type dimers, 3 A-type dimers, 2 B-type trimers, 1 A-type trimer, and 1 B-type tetramer were detected in the flesh, only 2 monomers, 1 B-type dimer, and 2 A-type dimers were detected in the endocarp. All PAs detected in the endocarp were also present in the flesh.

Ferulic acid dimers with phenylindane skeletons were obtained from ferulic acid 1 in an acidic ethanol solution. The reaction conditions used to prepare the dimers or the ester were examined in detail, and the stereochemistries of the dimers were determined. The structural features of the dimers and the diastereoselective formation mechanisms involved in forming the two types of dimers (the racemic diastereomer 8α, which was a major product, and the racemic diastereomer 8γ, which was a minor product) were characterized.

Intramolecular photocycloaddition of ferulic acid derivatives proceeded in high yields to give head-to-head intramolecular photodimers as three atropisomers. The photocycloaddition was sensitized by triplet sensitizers such as benzophenone, whereas photocycloreversion was promoted by 9,10-dicyanoanthracene (DCA) as an electron-transfer photocatalyst. On the other hand, intermolecular photocycloaddition afforded a head-to-tail photodimer. Scheme 1 Recently, much attention has been focused on the chemical and biological properties of ferulic acid derivatives including the anti-carcinogenesis and the anti-oxidation. 1 We have recently found a convenient method for the mass production of ferulic acid from the oily component of rice bran, which contribute to the eco chemistry. 2 Ferulic acid ( 1 ) and its derivatives are expected to be photochemically reactive, because the inter- and intra-molecular photocycloaddition of cinnamic acid and its derivatives have been widely investigated from the synthetic and mechanistic viewpoints. The topochemical intermolecular photocyclodimerization of cinnamic acid in solid states

We have recently developed novel resist materials for micro-lithographic patterning. One is a hydroxystyrene derivative, which is a key compound for KrF excimer laser resists. We found that microwave-assisted decarboxylation of hydroxycinnamic acids smoothly proceeded under the presence of a catalytic amount of amine base, to afford hydroxystyrene derivatives in good yield.The other is positive and negative-tone molecular resists utilizing the unique character of a furan ring. The synthesized compounds showed relatively high glass transition temperature and readily formed uniform amorphous films on a silicon wafer. The sensitivity as an EB resist of both positive and negative-tone resists was below 10 µC/cm2 and line and space patterns of 200 nm could be fabricated. The promising feature of the positive-tone resist is that no outgassed products from base matrixes are theoretically produced under the exposure and post-exposure bake procedure.

A novel positive-tone molecular resist possessing oxabenzonorbornadiene moiety was developed for electron-beam (EB) lithography. The synthesized resist material showed relatively high glass transition temperature and readily formed uniform amorphous films on a silicon wafer. The sensitivity of an EB resist was ca. 8 >μC. cm -2 and line and space patterns of 200 nm could be fabricated. The promising feature of the resist materials is that no outgassed products from base matrixes are theoretically produced under the exposure and post-exposure bake procedure.

A novel chemically amplified negative-tone molecular resist for electron-beam (EB) lithography was developed. The base matrix had six furan rings as a reactive functional group at its terminal. The resist containing the matrix, a crosslinker and a photoacid generator worked well as a negative-tone resist with high sensitivity (3 μC · cm -2 ). Line and space patterns (1:2) of 200 nm could be fabricated.

Phenols are deprotected with weak bases from their tert-butoxycarbonyl (Boc) derivatives. Boc deprotection with bases can avoid side reactions during the deprotection with acids. We note the lability of the Boc to bases and are able to utilize it as a new cleavage condition for synthetic studies.

Antioxidant activity and biological properties of ferulic acid (FA) are well recognized. This study was designed to estimate the potential utility of FA administered orally at low dosage for improvement of hyperglycemia in diabetes. With this aim we have evaluated the hypoglycemic effect of FA in two type diabetic animal models: (1) streptozotocin (STZ)-induced diabetic mice, a model of insulin-dependent diabetes mellitus (IDDM); (2) KK-Ay mice, a model of non-insulin dependent diabetes mellitus (NIDDM). In addition, we measured the production of thiobarbituric acid-reactive substances (TBARS) in brown adipose tissues of diabetic mice at the end of FA feeding experiment. FA at 0.01% and 0.1% of basal diet showed to suppress significantly blood glucose levels in STZ-induced diabetic mice. In KK-Ay mice 0.05% FA suppressed effectively blood glucose levels. In addition, FA inhibited the lipid peroxidation in brown adipose tissue of diabetic mice. Taken together, these findings suggest that dietary FA may be useful in alleviating oxidative stress and attenuating the hyperglycemic response associated with diabetes.

The authors prepared ferulic acid from rice bran pitch which was discharged in a process of the production of edible oil from rice bran and synthesized ethyl 3- (4-geranyloxy-3-methoxyphenyl) -2-propenoate (EGMP) using ferulic acid. EGMP was found to be a chemopreventive agent toward colon cancer in the rats. The condensation products consisting of ferulic and gallic acids showed strong antioxidative effects. Alkyl ferulates showed antimicrobial activity. Amide derivatives of ferulic acid were recognized as compounds accelerating secretion of insulin. The authors also synthesized nine bisferuloyl-myo-inositols, consisting of ferulic acid and myo-inositol moieties, using four key intermediates. These compounds showed the inhibitory effects on generation of tumor promoter 12-O-tetradecanoylphorbor-13-acetate (TPA) -induced superoxide in differentiated HL-60 cells, the suppressive effects on TPA-induced Esptein-Barr virus activation and the suppressive effects on cyclooxgenase-2 promoter activity. The authors prepared the derivative 42 which has i) a polyoxyethylene chain and methoxy groups on the phenyl rings for metal coordination, ii) aromatic rings for a π-π or CH-π interaction, and iii) carboxylic acids as a hydrogen-bonding moiety.

Objectives: We have previously observed the inhibitory effect of ferulic acid on rat tongue carcinogenesis. In this study, we investigated the modifying effects of a novel geranylated derivative, ethyl 3-(4′-geranyloxy-3′-methoxyphenyl)-2-propenoate (EGMP), synthesized from ferulic acid on tongue carcinogenesis initiated with 4-nitroquinoline 1-oxide (4-NQO). Methods: F344 male rats except those treated with EGMP alone and untreated rats were given 20 ppm 4-NQO in drinking water for 9 weeks to induce tongue neoplasms. Starting 1 week after the cessation of exposure to 4-NQO, the experimental groups given 4-NQO and a basal diet were fed the experimental diets containing EGMP (0.2% and 2%) for 20 weeks. The activities of glutathione S-transferase (GST) and quinone reductase (QR), the expression of proliferating cell nuclear antigen, polyamine content and ornithine decarboxylase activity in the tongue were examined for mechanistic analysis of modifying effects of EGMP on carcinogenesis. The expression of inducible nitric acid synthase (iNOS) was also assessed immunohistochemically. Results: At week 30, the incidence and multiplicity of tongue squamous cell carcinoma were significantly reduced by feeding of a 2% EGMP diet. EGMP feeding (2% in diet) elevated tongue GST activity and lowered QR activity in the tongue. Dietary EGMP decreased the expression of cell proliferation biomarker expression. Interestingly, EGMP feeding altered iNOS expression in the invasive parts of carcinoma. Conclusions: These results suggest that EGMP, when given at the 2% dose level during the promotion phase, exerts a chemopreventive action against tongue tumorigenesis through modification of cell proliferation activity and/or detoxifying enzymatic activity.

In our previous study, FA15 (2-methyl-1-butyl ferulic acid) was chemically synthesized as a novel ferulic acid (FA) analog, and found to notably suppress phorbol ester-induced Epstein-Barr virus activation and superoxide anion generation in vitro. In this report, we demonstrated that FA15, in contrast to FA, markedly suppressed the combined lipopolysaccharide and interferon-gamma-induced protein expressions of inducible nitric oxide synthase and cyclooxygenase-2, and also inhibited the release of tumor necrosis factor-alpha accompanied by suppression of I-kappa B degradation in RAW264.7, a murine macrophage cell line. In ICR mouse skin, topical application of FA15 significantly attenuated phorbol ester-triggered hydrogen peroxide production and edema formation as well as papilloma development while that of FA did not. Our results suggest that FA15, derived from natural sources, is a novel chemopreventive agent, both structurally and functionally.

Novel ferulic acid derivatives in which feruloyl groups were attached to the hydroxyl groups of myo-inositol 1,3,5-orthoformate derivatives were synthesized. These feruloyl-myo-inositols suppressed the cyclooxygenase-2 (COX-2) promoter activity in a concentration-dependent manner. Among the examined compounds, compound 9 showed the highest activity. A treatment with 100 μM of compound 9 for 24 h resulted in a 50% decrease of COX-2 promoter activity without marked cytotoxicity. Both the molecular structure in which two ferulic acid moieties are facing each other and the molecular hydrophobicity may be essential for the suppression of COX-2 promoter activity.

Tannin-like p-tert-butylcalix[4]arene 1,3-digallate was synthesized, and its conformational property was investigated by dynamic (1)H NMR and X-ray crystallography. It was found that the 3-OH (or 5-OH) group of the galloyl group in p-tert-butylcalix[4]arene 1,3-digallate is placed at the position where an unusual nonbonded close contact is observed between the OH group and the aromatic ring of the galloyl group facing each other. The calixarene 1,3-diesters of various hydroxybenzoic acids were also prepared, and the conformational properties of those calixarenes were compared with that of p-tert-butylcalix[4]arene 1,3-digallate. A significant contribution of the 3- and 5-OH groups in pendant groups toward the close contact was found. It was suggested that the conformation of p-tert-butylcalix[4]arene 1,3-digallate was stabilized by intramolecular hydrogen bonds including OH.O and OH-pi interactions.

The inhibitory influence of ferulic acid (FA), a rice germ component, and its geranylated derivative 3-(4'-geranyloxy-3-methoxyphenyl)-2-propenoate (EGMP) on the post-initiation stage of azoxymethane (AOM)-induced colon carcinogenesis was studied in male F344 rats given two s.c. injections of AOM (15 mg / kg body weight) during week 1. Diets containing EGMP or FA at doses of 0.1 or 0.2% were then fed for 3 weeks from week 2 to 5, when the animals were sacrificed. The numbers of aberrant crypt foci (ACF) and aberrant crypts (AC) per rat in the group given 0.2% FA were significantly decreased (P < 0.001) as compared to the AOM alone group. Furthermore, the numbers of ACF and AC per rat fed the 0.2% and 0.1% EGMP were significantly reduced (P < 0.001 and P < 0.01, respectively). Colonic epithelial cells in S-phase, as measured by bromodeoxyuridine (BrdU) labeling, in rats fed EGMP were significantly decreased in the 0.2 and 0.1% EGMP groups as compared to the AOM alone group (P < 0.05). BrdU labeling indices in rats fed FA and EGMP assessed by a test using a coefficient for linear contrast were also significantly decreased as compared to the AOM alone value (P < 0.05, P < 0.01, respectively). The results indicate that FA and EGMP have inhibitory effects on ACF and AC development, EGMP being more potent, possibly due to stronger suppressive effects on cell proliferation. No toxic effects were observed in rats given either compound in terms of body and organ weights, and liver or kidney histology. The findings thus suggest that EGMP and FA, especially the former, might have potential as chemopreventive agents against colon tumor development.

A total of 23 ferulic acid (FA) derivatives were synthesized, and investigated for their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate-induced Epstein-Barr virus (EBV) activation and superoxide (O(2)(-)) generation. Most of the derivatives showed significant EBV activation suppression or cytotoxicity at a concentration of 100 microM, with FA15 as the most potent suppressor. In both assays, FA6-FA17, bearing straight- or branched-alkyl side chains, exhibited marked suppression of O(2)(-) generation, with both FA16 and FA17 being highly active, while FA itself was virtually inactive. The activity differences seen between FA16/FA17 and FA are attributable, at least in part, to their cellular incorporating efficiencies. Further, both FA15 and FA21 attenuated the expression of inducible nitric oxide synthase and cyclooxygenase-2 proteins, while FA did not. Our results suggest that these novel FA derivatives are effective chemopreventive agents.

Studies were made on the polymorphism of p-tert-butylcalix[4]arene derivatives having amino acid groups on the lower rim to stabilize their hydrophilic pseudocavity by circular intramolecular hydrogen bonding. The calixarenes exhibit a polymorphic transformation upon heating in the solid state. This transformation is controlled by the thermal history of solids, accompanying the change on the conformation of the calixarene skeleton and also the change of hydrogen bonding in the hydrophilic pseudocavity.

A series of calix[6]arene-based surfactants have been synthesized, which contain amide oxime head groups on their upper rim and 5,5-dimethylhexyl (I), n-octyl (II), n-dodecyl (III), and n-hexadecyl (IV) groups on their lower rim. Composite membranes that were fabricated from Langmuir−Blodgett (LB) multilayers derived from each surfactant plus poly[1-(trimethylsilyl)-1-propyne] (PTMSP) cast film showed a significant increase in their selectivity toward helium and nitrogen, relative to bare PTMSP. In sharp contrast, analogous composites that were prepared with LB multilayers of conventional single chain surfactants [arachidic acid (AA), cadmium arachidate (AA/Cd2+), and stearoamideoxime (SA)] exhibited permeation properties that were identical with those of bare PTMSP. When a polymeric surfactant [poly(1-octadecene-co-maleic anhydride), POM] was used for LB film construction, a modest increase in selectivity was observed. These findings, together with an analysis of representative composites by X-ray photoe...

The formation of ethers was catalyzed by 5,11,17,23,29,35-hexa-p-t-butyl-37,38,39,40,41,42-hexakis(3,6,9-trioxadecyloxy)calix[6]arene (1). It was found that the calixarene-catalyzed reaction of phe...

This paper deals with the ability ofp-tert-butylcalix[6]arene derivative1, which has six 3,6,9-trioxadecyl substituents at the phenolic oxygens, to encapsulate CT complexes of alkadienes with iodine. By adding I2 to alkadienes in CH2Cl2 in the presence of1, the absorbance at 363 nm, which was ascribed to I3− ion, increased in the order: 1,5-hexadiene

The dichlorocarbene generation reaction from CHCl3 and solid KOH in CH2Cl2 was catalyzed by the p-t-butylcalix[6]arene derivative 1 which bears six 3,6,9-trioxadecyl substituents on the phenolic oxygens. Dichlorocarbene generated by this method reacted efficiently with alkenes and amides to give dichlorocyclopropane derivatives and nitriles, respectively, in high yields. The reaction with alkadiene having isolated double bonds gave mixtures of the mono- and bis-dichlorocarbene adducts, but the monoadduct formation always predominated. The catalytic action of the calixarene and the reactivity features of dichlorocarbene generated by the above procedure are discussed on the basis of kinetic measurements. They are also compared with those of the 18-crown-6-catalyzed reactions.

The binding properties of p-(phenylazo)calix[n]arenes (n = 6 and n = 4) for metal ions have been studied. The calixarenes show a highly selective binding ability toward Ag+, Hg+, and Hg2+. This property can be explained in terms of a metal ion-induced azo/hydrazone tautomerism. The Ag+ ion forms complexes with the azocalixarenes by binding with their hydrazone tautomers.

Calix[4]quinone (7) and calix[4]hydroquinone (6) have been synthesized using three different synthetic pathways, The first pathway to 7 from calix[4]arene (1) consists of six steps: acetylation, Fries rearrangement, Baeyer-Villiger oxidation after acetylation, hydrolysis, and oxidation. The second pathway to 7 from 1 consists of four steps: acetylation, Fries rearrangement, reaction of the product obtained by Fries rearrangement with sodium azide, and oxidation.The NMR behavior of 6 and 7 is described

The calix[6]arene 1 bearing six trioxadecyl groups on the phenolic oxygens served as an effective catalyst for the oxidation of alkenes, alkynes, and alcohols with KMnO4 in CH2Cl2. The reaction of ...

The formation of ethers was catalyzed by 5,11,17,23,29,35-hexa-p-t-butyl-37,38,39,40,41,42-hexakis(3,6,9-trioxadecyloxy)calix[6]arene (1). It was found that the calixarene-catalyzed reaction of phe...

Novel ferulic acid derivatives in which feruloyl groups were attached to the hydroxyl groups of myo-inositol 1,3,5-orthoformate derivatives were synthesized. These feruloyl-myo-inositols suppressed the cyclooxygenase-2 (COX-2) promoter activity in a concentration-dependent manner. Among the examined compounds, compound 9 showed the highest activity. A treatment with 100 μM of compound 9 for 24 h resulted in a 50% decrease of COX-2 promoter activity without marked cytotoxicity. Both the molecular structure in which two ferulic acid moieties are facing each other and the molecular hydrophobicity may be essential for the suppression of COX-2 promoter activity.

We prepared novel polyphenols which were esters composed of two naturally occurring products, ferulic and gallic acids, and investigated their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced Epstein–Barr virus (EBV) activation and superoxide (O2−) generation. Most of these compounds exhibited significant EBV activation suppression at a concentration of 20 μM and in particular, the ester 5f having 2-metyl-1-butyl group showed high activity. The suppressive effects on O2− generation were also observed in most of the esters.

Calix[4]arene derivatives bearing carboxyl groups at the upper rim and alkyl groups at the lower rim were synthesized. Micrometer-size porous honeycomb-patterned thin films were prepared by evaporating chloroform solution of polystyrene containing the calixarene derivatives under high humidity. These films were coated on gold electrodes of QCM, and the high-frequency changes were observed to detect volatile organic compounds such as dichlorobenzene.

Calix[4]quinone (7) and calix[4]hydroquinone (6) have been synthesized using three different synthetic pathways, The first pathway to 7 from calix[4]arene (1) consists of six steps: acetylation, Fries rearrangement, Baeyer-Villiger oxidation after acetylation, hydrolysis, and oxidation. The second pathway to 7 from 1 consists of four steps: acetylation, Fries rearrangement, reaction of the product obtained by Fries rearrangement with sodium azide, and oxidation.The NMR behavior of 6 and 7 is described

p-tert-Butylcalix[4]arene 1,3-digallate, which contains a nonbonded close contact between galloyl groups, was synthesized and its structure was determined by dynamic (1)H NMR and X-ray crystallography. The electronic spectra showed that a new absorption band of the complexes appeared at a longer wavelength region upon adding Ag(+) ion. This spectral shift was explained in terms of the interaction between the facing galloyl groups of the lower rim of the calixarene framework.

5,11,17,23,29,35-Hexa-p-tert-butyl-37,38,39,40,41,42-hexakis(3,6,9-trioxadecyloxy)calix[6]arene efficiently catatalyzes the reaction of alkyl halides with alkali metal carboxylates to produce esters.

Plasmon absorption of silver colloid, which was formed by reduction of silver ion with compounds bearing gallate ester groups in ethanol, was observed by absorption spectroscopy. The time-dependent absorption of silver colloid was found, which shows that the silver colloid is unstable and easy to aggregate. It seemed that a calixarene derivative bearing two gallate ester groups was the most suitable for determining silver ion. In order to prevent the silver colloid aggregation, poly( N -vinylpyrrolidone) (PVP) was added into the solution at a constant time after the preparation of sample solutions. In the calibration graph, the absorbance increased with increasing silver ion concentration, especially in the concentration range of 2.00 × 10 −6 to 1.00 × 10 −5 M. It is possible to determine silver ion concentrations using this method.

We prepared amide compounds which were derived from ferulic acid using various amines, and investigated their stimulatory effects on insulin secretion using rat pancreatic RIN-5F cells. Most of these compounds exhibited significant promotion of the insulin-release at a concentration of 10 μM and in particular, the amides having n-butyl, n-pentyl, pyrrolidine, and piperidine groups showed high activity.

The calix[6]arene 1 bearing six trioxadecyl groups on the phenolic oxygens served as an effective catalyst for the oxidation of alkenes, alkynes, and alcohols with KMnO4 in CH2Cl2. The reaction of ...

Ferulic acid derivative assembles with three kinds of non-covalent interactions, i.e., metal coordination, hydrogen bonding and CH-pi interaction: X-ray crystallographic study illustrated the molecular assembly mode.

We prepared 14 feruloyl- myo -inositol derivatives, and evaluated the relationships between their stereostructure and inhibitory activity toward the 12- O -tetradecanoylphorbol-13-acetate (TPA)-induced superoxide (O 2 − ) generation. And further, their suppressive effect on the TPA-induced Epstein–Barr virus (EBV) activation was examined in order to estimate their anti-carcinogenic potentials. Among the derivatives tested, 1,6- O -bis[3-(4′-hydroxy-3′-methoxyphenyl)-2-propenoyl]- myo -inositol ( 6b ) showed an excellent suppressive activity on the O 2 − generation at a concentration of 20 μM. For the suppressive effects on the EBV activation, 2,4,6- O -tris[3-(4′-hydroxy-3′-methoxyphenyl)-2-propenoyl]- myo -inositol 1,3,5-orthoformate ( 9b ) showed the highest activity at a concentration of 100 μM among the derivatives tested. These results suggest that the inhibitory potencies of feruloyl- myo -inositol derivatives depend on the stereostructure of molecules rather than the hydrophobicity of molecules.

We prepared novel polyphenols which were esters composed of two naturally occurring products, ferulic and gallic acids, and investigated their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced Epstein–Barr virus (EBV) activation and superoxide (O2−) generation. Most of these compounds exhibited significant EBV activation suppression at a concentration of 20 μM and in particular, the ester 5f having 2-metyl-1-butyl group showed high activity. The suppressive effects on O2− generation were also observed in most of the esters.

Calix[4]arenes bearing amino acid moieties were prepared by the reaction of carboxyl-protected amino acids with the acid chlorides of O-carboxymethylcalix[4]arenes. The binding ability toward metal ions was estimated by solvent extraction. These calixarenes showed selective extraction capability toward Na(+) and Ag(+) ions, which increased in the order 2a < 2b < 2d < 2c. The complexing ability was also affected by the nature of the solvents and was higher in ethyl acetate than dichloromethane. (1)H NMR studies showed that the complexation of 2c with Na(+) ion induces a change of the orientation of the amide groups from a network-like pattern with circular N-H- - -O=C intramolecular hydrogen bonding of 2c to a pattern in which carbonyl groups converge on the Na(+) ion. This change was also supported by a measurement of CD spectra.

Studies were made on the polymorphism of p-tert-butylcalix[4]arene derivatives having amino acid groups on the lower rim to stabilize their hydrophilic pseudocavity by circular intramolecular hydrogen bonding. The calixarenes exhibit a polymorphic transformation upon heating in the solid state. This transformation is controlled by the thermal history of solids, accompanying the change on the conformation of the calixarene skeleton and also the change of hydrogen bonding in the hydrophilic pseudocavity.

Ester compounds consisting of ferulic acid and myo-inositol, obtained from rice bran, were synthesized. The inhibitory effects of these feruloyl-myo-inositols on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced superoxide (O2−) generation were examined using differentiated HL-60 cells. Among the derivatives tested, only 3,4,5,6-tetra-O-acetyl-1,2-di-O-[3-(4′-acetoxy-3′-methoxyphenyl)-2-propenoyl]-myo-inositol (3) showed a distinct inhibitory activity.

Two novel optically active myo-inositol derivatives having a bulky alkyl–silyl group as a hydrophobic part were synthesized. These compounds acted as a gelator toward nonpolar hydrophobic solvents such as n-hexane, cyclohexane, and toluene via the formation of an intermolecular OH···O hydrogen bonding network.

The title compound, C22H30O4, is known as a chemopreventive agent against colon tumor development. The molecular structure is nearly planar, showing a trans arrangement with respect to the C=C bond of the phenyl­propenoate moiety.

Rapid preparation of p-tert-butylcalix[4]arene using microwave irradiation was studied and p-tert-butylcalix[4]arene was obtained as a pure form in modest yield with shortening the reaction time from hours to minutes.

Calix[4]quinone and other functionalized calixarenes were synthesized in high yields. The crystal structure of the calix[4]quinone was determined by the X-ray diffraction method.