Abstract: The invention relates to a method for the storage of cooling agents without caking, characterized in that the latter are filled into standard packages having a maximum capacity of 25 l, with the proviso that (a) the packages are filled to 50% maximum, and (b) the amount filled into the package does not exceed 10 kg.

Abstract: The present invention relates to an optically active axially chiral ?-allenic alcohol, a synthetic method and use thereof. A method of preparing a high optically active chiral ?-allenic alcohol by using propargyl alcohol, aldehyde and chiral ?,?-diphenyl-L-prolinol under the protection of tert-butyldimethylsilyl with a mediator zinc bromide. The axially chiral ?-allenic alcohol has the structural formula (I). The method of the present invention has the following advantages: the synthesis route is short, operations are simple, raw materials are readily available, separation and purification are convenient, the substrate has high generality, the total yield is high, and enantioselectivity and diastereoselectivity are high.

Abstract: A process for the preparation of 1-ethynyl-3,3-dimethylcyclohexan-1-ol from dimedone by a reaction sequence of reduction and ethynylation and its further transformation into green ketone.

Abstract: The invention relates to the chemistry of fragrances and to the field of perfumery. It relates more particularly to compounds with a woody note, responding to the general formula: in which: the ring with 6 carbon atoms is saturated or has a double bond between carbons C1 and C2 or between carbons C1 and C6, R is selected from a C2-C5 alkyl or C2-C5 alkenyl group.

Abstract: This invention discloses 2-methylene-vitamin D analogs, and specifically (20S)-1?,25-dihydroxy-2-methylene-vitamin D3 as well as (5E)-(20S)-1?,25-dihydroxy-2-methylene-vitamin D3 and (20R)-1?,25-dihydroxy-2-methylene-vitamin D3, as well as pharmaceutical uses therefor. These compounds exhibit relatively high binding activity and pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent especially for the treatment or prevention of osteosarcoma, leukemia, colon cancer, breast cancer, skin cancer or prostate cancer. These compounds also have relatively high calcemic activities evidencing use in the treatment of bone diseases.

Abstract: The present invention provides a method of treating glaucoma or ocular hypertension which comprises applying to the eye of a person in need thereof an amount sufficient to treat glaucoma or ocular hypertension of a compound of formula I wherein Y, Q, Z, R, R1 and R2 are as defined in the specification. The present invention further comprises pharmaceutical compositions, e.g. ophthalmic compositions, including said compound of formula I.

Abstract: The present invention provides a substance which promotes the transdermal absorption of a pharmacologically active component while little irritating the skin. The present invention relates to a transdermal absorption promoter which comprises, as the active component, at least one member selected from among isopulegol, 2-(menthoxy)ethanol and 2-methyl-3-(menthoxy)propane-1,2-diol; and an external skin formulation which comprises a pharmacologically active component such as a psychotropic component, an anti-inflammatory component, an analgesic component, an antipyretic component, a whitening component or a hair growth-promoting component, together with the aforesaid transdermal absorption promoter.

Abstract: Provided is a process in which cyclization of a compound having, in a molecule, a formyl group and a double bond which allow carbonyl-ene cyclization, the compound existing as a mixture of optical isomers thereof, increases the ratio of a particular optical isomer not only in a cyclized compound, but also in an unreacted compound. The process comprises performing, in the presence of a specified aluminum complex represented by the general formula: [Al2(L1)n(L2)3-n]m, cyclization of a compound having, in a molecule, a formyl group and a double bond which allow carbonyl-ene cyclization, the compound existing as a mixture of optical isomers thereof, to increase the ratio of a particular optical isomer.

Abstract: A catalyst for obtaining isopulegol of high diastereoselectivity by highly selective cyclization reaction of citronellal is provided. The present invention relates to an organoaluminum compound obtained by reacting at least one organoaluminumoxy compound selected from the group consisting of chain aluminoxanes, cyclic aluminoxanes and bis(dialkylaluminumoxy)alkylboranes, with at least one hydroxy compound selected from the group consisting of diarylphenols, bis(diarylphenol) compounds, biaryldiols, dimethanols and silanols.

Abstract: A process for the preparation of 1-ethynyl-3,3-dimethylcyclohexan-1-ol from dimedone by a reaction sequence of reduction and ethynylation and its further transformation into green ketone.

Abstract: The present invention relates to the field of perfumery. More particularly, it concerns specific derivatives of 1-alkenyl cyclopentanol, or 1-alkenyl cyclohexanol, wherein the alkenyle group is branched. These compounds are useful perfuming ingredients capable of imparting sap and/or earthy notes.

Abstract: The present invention relates to a method of working up an aluminium-containing reaction product from the production of isopulegol by cyclization of citronellal in the presence of complex compounds, comprising at least one ligand of the formula (I), where Ar1, Ar2, Ar3, Ar4 are chosen from C6-C15-aryl or C2-C15-hetero; R1, R2, R3, R4 are chosen from H, C1-C6-alkyl, C1-C6-perfluoroalkyl, C1-C6-alkoxy, C7-C12-aralkyl, halogen, SiR5bR6bR7b, C6-C10-aryl, NR8bR9b, SR10b, NO2; and where R1 or R2 and/or R3 or R4, together with A, can form an aromatic or nonaromatic cycle; etc.; in which a) the aluminum-containing reaction product is subjected to distillative separation, b) the isopulegol-depleted bottom product is brought into close contact with an aqueous base and c) the ligand of the formula (I) is separated off from the organic phase, preferably by crystallization. Moreover, the invention relates to a method of producing isopulegol, and to a method of producing menthol.

Abstract: To provide a process for increasing the proportion of an optical isomer of not only a compound having a closed ring but also a compound not having a closed ring when an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule is subjected to a ring closing reaction. A process for increasing the proportion of an optical isomer characterized by subjecting an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule to a ring closing reaction in the presence of a predetermined aluminum complex represented by the general formula: [Al1(L1)1(L2)m(Lh)n]k.

Abstract: A catalyst for obtaining isopulegol of high diastereoselectivity by highly selective cyclization reaction of citronellal is provided. The present invention relates to an organoaluminum compound obtained by reacting at least one organoaluminumoxy compound selected from the group consisting of chain aluminoxanes, cyclic aluminoxanes and bis(dialkylaluminumoxy)alkylboranes, with at least one hydroxy compound selected from the group consisting of diarylphenols, bis(diarylphenol) compounds, biaryldiols, dimethanols and silanols.

Abstract: To provide a process for increasing the proportion of an optical isomer of not only a compound having a closed ring but also a compound not having a closed ring when an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule is subjected to a ring closing reaction. A process for increasing the proportion of an optical isomer characterized by subjecting an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule to a ring closing reaction in the presence of a predetermined aluminum complex represented by the general formula: [Al2(L1)n(L2)3-n]m.

Abstract: The present invention relates to a method of working up an aluminum-containing reaction product from the production of isopulegol by cyclization of citronellal in the presence of complex compounds, comprising at least one ligand of the formula (I), where R1, R2, R3 are chosen from hydrogen, halogen, nitro, C1-C8-alkyl, C1-C8-alkoxy, di(C1-C4-alkyl)amino and aryl; R4, R5 are chosen from halogen, nitro, C1-C8-alkyl, C1-C8-alkoxy, di(C1-C4-alkyl)amino, aryl or heteroaryl; in which a) the reaction product is subjected to distillative separation to obtain an isopulegol-enriched top product and an isopulegol-depleted bottom product and b) the ligand of the formula (I) is separated off from the bottom product. Moreover, the invention relates to a method of producing isopulegol, and to a method of producing menthol.

Abstract: Provided is a process in which cyclization of a compound having, in a molecule, a formyl group and a double bond which allow carbonyl-ene cyclization, the compound existing as a mixture of optical isomers thereof, increases the ratio of a particular optical isomer not only in a cyclized compound, but also in an unreacted compound. The process comprises performing, in the presence of a specified aluminum complex represented by the general formula: [Al2(L1)n(L2)3-m]m, cyclization of a compound having, in a molecule, a formyl group and a double bond which allow carbonyl-ene cyclization, the compound existing as a mixture of optical isomers thereof, to increase the ratio of a particular optical isomer.

Abstract: The present invention relates to a process for the preparation of a compound of the formula B having the following steps: provision of a compound of the formula A intramolecular reaction of the compound of the formula A in the presence of an aluminium siloxide of the formula (Ia) or (Ib).

Abstract: The present invention relates to a process for preparing enriched isopulegol by crystallization from a melt comprising isopulegol. The invention relates specifically to a process for preparing enantiomerically enriched n-isopulegol proceeding from optically active isopulegol having a relatively low enantiomeric excess by crystallization from the melt. The invention further relates to a process for preparing menthol proceeding from enantiomerically and/or diastereomerically enriched n-isopulegol prepared by crystallization from the melt.

Abstract: An antidiarrhetic composition is provided which is efficacious against diarrhea, in particular, the predominant secretory diarrhea; an antidiarrhetic medicinal composition containing the same is also provided; a food containing the antidiarrhetic composition is also provided; and a method of preventing diarrhea using the same is also disclosed. The composition for relieving diarrhea is a cool composition capable of acting on the digestive tract in the recipient's body and inhibiting the secretion of the intestinal Cl?. In other words, a composition containing one or more kinds of cool act compounds. It may be provided by adding to medicines, foods or drinks.

Abstract: The invention provides compounds having the following general formula (I): wherein X, R1, R2, R7 and Z are as described here.

Abstract: The present invention relates to a method of working up an aluminum-containing reaction product from the production of isopulegol by cyclization of citronellal in the presence of complex compounds, comprising at least one ligand of the formula (I), where R1, R2, R3 are chosen from hydrogen, halogen, nitro, C1-C8-alkyl, C1-C8-alkoxy, di(C1-C4-alkyl)amino and aryl; R4, R5 are chosen from halogen, nitro, C1-C8-alkyl, C1-C8-alkoxy, di(C1-C4-alkyl)amino, aryl or heteroaryl; in which a) the reaction product is subjected to distillative separation to obtain an isopulegol-enriched top product and an isopulegol-depleted bottom product and b) the ligand of the formula (I) is separated off from the bottom product. Moreover, the invention relates to a method of producing isopulegol, and to a method of producing menthol.

Abstract: The present invention relates to a method of working up an aluminium-containing reaction product from the production of isopulegol by cyclization of citronellal in the presence of complex compounds, comprising at least one ligand of the formula (I), where Ar1, Ar2, Ar3, Ar4 are chosen from C6-C15-aryl or C2-C15-hetero; R1, R2, R3, R4 are chosen from H, C1-C6-alkyl, C1-C6-perfluoroalkyl, C1-C6-alkoxy, C7-C12-aralkyl, halogen, SiR5bR6bR7b, C6-C10-aryl, NR8bR9b, SR10b, NO2; and where R1 or R2 and/or R3 or R4, together with A, can form an aromatic or nonaromatic cycle; etc.; in which a) the aluminum-containing reaction product is subjected to distillative separation, b) the isopulegol-depleted bottom product is brought into close contact with an aqueous base and c) the ligand of the formula (I) is separated off from the organic phase, preferably by crystallization. Moreover, the invention relates to a method of producing isopulegol, and to a method of producing menthol.

Abstract: The present invention provides a method of treating glaucoma or ocular hypertension which comprises applying to the eye of a person in need thereof an amount sufficient to treat glaucoma or ocular hypertension of a compound of formula I wherein Y, Q, Z, R, R1 and R2 are as defined in the specification. The present invention further comprises pharmaceutical compositions, e.g. ophthalmic compositions, including said compound of formula I.

Abstract: The present invention relates to diarylphenoxyaluminum compounds which are obtainable by reacting a bis(diarylphenol) ligand of the formula (I) with an alkylaluminum compound and/or a complex aluminum hydride. The invention moreover relates to the use of such diarylphenoxyaluminum compounds as catalysts. Moreover, the invention relates to a method of producing isopulegol by cyclization of citronellal in the presence of diarylphenoxyaluminum compounds as catalysts. The invention also relates to a method of producing menthol by cyclization of citronellal in the presence of diarylphenoxyaluminum compounds as catalysts and subsequent hydrogenation.

Abstract: The present invention relates to novel substituted cyclohexyl monohydric alcohols possessing woody odor which are useful as fragrance materials. The invention also provides method for synthesis of the above compounds. The invention also provides fragrance compositions which utilize the compounds of the invention to impart woody aroma to such compositions.

Abstract: 13,13-Dimethyl-des-C,D analogs of 1?,25-dihydroxy-19-nor-vitamin D3 compounds and topical composition dosage forms thereof, and methods of treating skin conditions thereof. Exemplary active pharmaceutical ingredients include (1R,3R)-5-[(E)-(S)-11?-hydroxy-5?,5?,7?,11?-tetramethyl-dodec-2?-enylidene]-2-metylene-cyclohexane-1,3-diol, (1R,3R)-5-[(Z)-(S)-11?-hydroxy-5?,5?,7?,11?-tetramethyl-dodec-2?-enylidene]-2-metylene-cyclohexane-1,3-diol, (1R,3R)-5-[(E)-(R)-11?-hydroxy-5?,5?,7?,11?-tetramethyl-dodec-2?-enylidene]-2-metylene-cyclohexane-1,3-diol, and (1R,3R)-5-[(Z)-(R)-11?-hydroxy-5?,5?,7?,11?-tetramethyl-dodec-2?-enylidene]-2-metylene-cyclohexane-1,3-diol.

Abstract: The use as fragrance ingredient of a compound of formula (I) wherein R1 and Y have the same meaning as given in the description, and fragrance applications comprising them.

Abstract: The present invention relates to a process for the preparation of isopulegol of formula (I): comprising the cyclization of citronellal of formula (II): in the presence of a tris(aryloxy)aluminum catalyst, wherein the cyclization is carried out in the presence of I. at least one acid and/or II. at least one compound selected from the group comprising carboxylic anhydrides, aldehydes, ketones and vinyl ethers.

Abstract: The present invention relates to a process for the preparation of a compound of the formula B having the following steps: provision of a compound of the formula A intramolecular reaction of the compound of the formula A in the presence of an aluminium siloxide of the formula (Ia) or (Ib).

Abstract: The present invention relates to a process for preparing enriched isopulegol by crystallization from a melt comprising isopulegol. The invention relates specifically to a process for preparing enantiomerically enriched n-isopulegol proceeding from optically active isopulegol having a relatively low enantiomeric excess by crystallization from the melt. The invention further relates to a process for preparing menthol proceeding from enantiomerically and/or diastereomerically enriched n-isopulegol prepared by crystallization from the melt.

Abstract: Provided is a crystallization method for reducing the level of impurities in calcipotriene in which a solution of a starting calcipotriene in a first process solvent, for example THF, is combined with second process solvent, for example methyl formate, and, after cooling, calcipotriene is isolated. The method can include a slurry step for reducing the level of residual first process solvent.

Abstract: A process for producing l-isopulegol by simple operations with safety in high yield. A process for producing isopulegol, which comprises selectively cyclizing citronellal in the presence of a tris(2,6-diarylphenoxy)aluminum catalyst represented by the following general formula (3): wherein Al represents an aluminum atom, Ar1 and Ar2 each represent a substituted or unsubstituted aryl group or a heteroaryl group; and R1, R2 and R3 each represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atom(s), an alkoxy group having 1 to 8 carbon atom(s), a substituted or unsubstituted aryl group, a dialkylamino group having 1 to 4 carbon atom(s), or a nitro group.

Abstract: A process for the preparation of optically pure acetylenediols of the formulae R-I and S-I and their further reaction to give meso-zeaxanthin are described.

Abstract: Free perfluorosulfonylmethide compounds and metal salts thereof show strong catalytic activity in carbon-carbon bond formation reactions, in amounts as low as 0.1 mole %. Fluorous media may be used, especially biphasic fluorous media enabling ready recycling of the catalyst. The formula thereof is: M[C(SO2R1)3−(m+q)(SO2R2)m(SO2R3)q]x where M is H, Sc, Y, La, Ce, Pr, Nd, Sm Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Zr, Hf, Th, Nb, Ta, U, Bi, Al, Ga, In or Tl, x is the common oxidation state of a said metal M, R1, R2 and R3 are perfluorinated or polyfluoronated hydrocarbon, ether or amine moieties or mixtures thereof and m+q=0, 1, 2 or 3 (m and q being zero or integers).

Abstract: The present invention provides a process for producing an acetylenediol continuously by reacting a ketone with acetylene in the presence of an alkali catalyst, which process comprises continuously feeding, into a first-stage reactor, a reaction solvent, an alkali catalyst, a ketone and acetylene to give rise to a reaction, continuously introducing the reaction mixture into a second-stage reactor, and continuously feeding a fresh portion of the same ketone into the second-stage reactor to give rise to a reaction.

Abstract: A process for producing l-isopulegol by simple operations with safety in high yield.

Abstract: A cis-olefin of the formula: R1—CH═CH—R2 is prepared by reducing an alkyne of the formula: R1—C≡C—R2 with formic acid in the presence of a palladium catalyst. R1 and R2 are independently selected from the group consisting of a hydrogen atom, ester group, substituted silyl group, carboxyl group, cyano group, aliphatic C1-C20 hydrocarbon group, and phenyl group. The cis-olefin which is a useful intermediate for the synthesis of fine chemicals is selectively produced in high yields.

Abstract: A new process prepares retiferol derivatives of formula I: wherein A is —C ≡C— or —CH═CH—, and R1 and R2 are independently of each other lower alkyl or lower perfluoroalkyl, one version couples ketones of formula 1I with compounds of formula III A second version couples phosphinoxides of formula IV with aldehydes of formula V. Compounds of formula I are useful in the treatment or prevention of hyperproliferative skin diseases and for reversing the conditions associated with photodamage.

Abstract: There is described a process of transferring &agr;,&bgr;-unsaturated alkyl groups to an electrophile (aldehyde, ketone, nitrile, imine, alkyne) by means of a masked zinc alkyl in an aprotic solvent.

Abstract: Compounds of formula I wherein X is C═CH2 or CH2; Y and Z are independently of each other hydrogen, fluorine or hydroxy; A is —C≡C—, —CH═CH— or —CH2—CH2—, R1 and R2 are independently of each other alkyl or perfluoroalkyl; and R3 is lower alkyl are useful in the treatment or prevention of hyperproliferative skin diseases, particularly psoriasis, basal cell carcinomas, disorders of keratinization and keratosis; or for reversing the conditions associated with photodamage.

Abstract: An active highly acidic microporous solid catalyst comprising sulphated metal oxide and at least one of carbon molecular sieve and/or heteropoly acid and having pore volume in the range of 0.1-0.2 m3/g and pore size distribution in the range of 25-40 Å for use in acid catalized organic reactions which occur in the microporous range of the catalysts such as nitration of aromatic compounds, cyclization of terpenoids and more particularly relates to the preparation of modified sulphated zirconia catalysts. The invention also covers the process for producing the abovesaid solid catalyst and its use in producing isopulegol-rich in 1-isopulegol isomer from d-citronellal and in process for mononitration of aromatic compounds C6H4R1R2 wherein R1=—CH3, —C2H5, —Cl, —Br or —I and R2—H or —CH3.

Abstract: This invention relates to a process for producing 2-substituted succinate esters of formula (I) by reacting (a) a dicarboxylic compound with a first alcohol R'O[CH'.CH.sub.2 O].sub.x H where x is 0 or an integer from 1-6 in the presence of a catalyst to form a hydrocarbyl ester or, when x=1-6, a hydrocarbyloxy alkylene ester of maleic and/or fumaric acid and (b) the ester from step (a) with an alkaline earth metal alkoxide in the presence of a second alcohol R.OH to form the 2-substituted succinate ester of formula (I). The esters and paint formulations based thereon are also claimed.

Abstract: The compound, (E)-(1R,3R)-5-[(R)-11-hydroxy-7,11-dimethyl-dodec-2-enylidene]-cyclohexane -1,3-diol of the formula I: ##STR1## is useful in the treatment or prevention of hyperproliferative skin diseases, particularly psoriasis, basal cell carcinomas, disorders of keratinization and keratosis; or for reversing the conditions associated with photodamage.

Abstract: This invention provides a novel class of vitamin D related compounds, namely, the 2-alkylidene-19-nor-vitamin D derivatives, as well as a general method for their chemical synthesis. The compounds have the formula: ##STR1## where Y.sub.1 and Y.sub.2, which may be the same or different, are each selected from the group consisting of hydrogen and a hydroxy-protecting group, R.sub.6 and R.sub.8, which may be the same or different, are each selected from hydrogen, alkyl, hydroxyalkyl and fluoroalkyl, or when taken together represent the group --(CH.sub.2).sub.x -- where x is an integer from 2 to 5, and where the group R represents any of the typical side chains known for vitamin D type compounds. These 2-substituted compounds are characterized by low intestinal calcium transport activity and high bone calcium mobilization activity resulting in novel therapeutic agents for the treatment of diseases where bone formation is desired, particularly low bone turnover osteoporosis.

Abstract: Compounds of formula I: ##STR1## wherein the dotted carbon-carbon bond in the D-ring is C--C or C.dbd.C; C(R,R) is CH.sub.2 or C.dbd.CH.sub.2,R.sup.1 is H, F or OH,R.sup.2 and R.sup.3 are each independently C.sub.1-4 -alkyl or CF.sub.3, or together with the carbon to which they are bound form C.sub.3-6 -cycloalkyl.are useful in the treatment of vitamin D dependent disorders, such as psoriasis, leukemia; acne and seborrhoic dermatitis; osteoporosis hyperparathyroidism accompanying renal failure; and multiple sclerosis.

Abstract: The present invention relates to a modified Raney nickel catalyst which can serves as hydrogenation catalyst for hydroxy aldehydes, such as 4-hydroxy-butanal, and 2-methyl-3-hydroxypropanal and hydroxy cyclic ethers such as 2-hydroxy-tetrahydrofuran. Further, a process for preparing diols by using the modified Raney nickel catalyst is provided.

Abstract: A liquid l-n-menthol composition containing 30 to 80% by weight of (-)-n-isopulegol and a process for preparing a liquid l-n-menthol composition comprising mixing 20 to 70 parts by weight of liquid menthol at a temperature of not lower than 42.degree. C. as obtained in the production of l-n-menthol with 30 to 80 parts by weight of (-)-n-isopulegol are disclosed. Further, the liquid l-n-menthol composition in which part of the (-)-n-isopulegol is replaced with 3-l-n-menthoxypropane-1,2-diol and the process for preparing the same are also disclosed. The liquid l-n-menthol composition of the present invention is less expensive than conventionally available menthol and yet has an improved feeling of coolness (particularly, the bitterness is reduced) and can be used in place of conventional menthol. Besides, the liquid menthol composition of the present invention is excellent in workability and hygiene on use.

Abstract: The invention relates to a compound selected from these of formula (I): ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and B are as defined in the description, their enantiomers and diastereoisomers, their Z and E isomers, and their addition salts with a pharmaceutically-acceptable acid or base, and medicinal products containing the same which is useful for treating a disorder selected from an inflammatory disorder and a pathological inflammatory condition.

Abstract: This invention provides a purified retro-retinoid compound characterized by a molecular mass of about 302 daltons. Also provided by this invention is a method of enhancing the growth of a cell in a vitamin A reduced environment which comprises contacting the cell with an effective growth enhancing amount of a compound having a structure: ##STR1## wherein the configuration of the C6, C8, C10 and C12 double bond independently is Z or E and the absolute configuration at C-14 is independently R or S; wherein R.sub.1 is alkyl, alkyl halide, alcohol, ester, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, acid halide, amide, nitrile, or amine; and wherein R.sub.2 is hydroxyl, halide, alkoxy, ester, alkyl, alcohol, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, nitrile, amine, azide, alkyl halide, acid halide, acid azide, or amide; or wherein R.sub.1 and R.sub.2 are replaced by a 14, 15-oxirane group; and wherein the retro structure is alpha or gamma.