The present application relates to the preparation of cyclohexyl-alkyl carbinols, including 1-(cyclohex-3-en-1-yl)-2-methylpropan-1-ol, which possesses a minty aroma that can be described as fresh, invigorating, and menthol-like, and also possesses cooling properties. The use of cyclohexyl-alkyl carbinols as readily accessible and cost effective fragrance, flavor, and cooling ingredients, and potential applications thereof is also described.

Provided are colored 1,4-benzoquinone compounds obtained by oxidation of precursor molecules from the venom of the scorpion Diplocentrus melici (Diplocentridae family). Schemes for the chemical synthesis of these compounds using reagents commercially available are also provided. Biological assays show that the red compound (3,5-dimethoxy-2-(methylthio)cyclohexa-2,5-diene-1,4-dione) is very effective at killing Staphylococcus aureus and that the blue compound (5-methoxy-2,3-bis(methylthio)cyclohexa-2,5-diene-1,4-dione) has remarkable activity against Mycobacterium tuberculosis. The blue compound is effective against multi-drug-resistant tuberculosis (MDR-TB) and is not detrimental to lung epithelium. Both compounds were found to be cytotoxic to human neoplastic cell lines and to mononuclear cells (PBMCs).

Provided are colored 1,4-benzoquinone compounds obtained by oxidation of precursor molecules from the venom of the scorpion Diplocentrus melici (Diplocentridae family). Schemes for the chemical synthesis of these compounds using reagents commercially available are also provided. Biological assays show that the red compound (3,5-dimethoxy-2-(methylthio)cyclohexa-2,5-diene-1,4-dione) is very effective at killing Staphylococcus aureus and that the blue compound (5-methoxy-2,3-bis(methylthio)cyclohexa-2,5-diene-1,4-dione) has remarkable activity against Mycobacterium tuberculosis. The blue compound is effective against multi-drug-resistant tuberculosis (MDR-TB) and is not detrimental to lung epithelium. Both compounds were found to be cytotoxic to human neoplastic cell lines and to mononuclear cells (PBMCs).

A homogeneous catalytic reaction method and a catalyst for isomerization and hydroformylation of long-chain internal olefins are disclosed. A rhodium-ruthenium metal complex is used as a catalyst; and the ligands are tetradentate phosphine ligands. By means of the catalytic system, homogeneous internal olefin isomerization aid hydroformylation can be performed under a certain temperature and pressure to obtain aldehyde products having high normal to iso ratios. The present invention is applicable to not only long-chain internal olefins (C8) but also internal olefins having a carbon number less than 8.

Methods for preparing a variety of ladderane precursors, ladderane compounds and ladderane lipids are provided. Also provided are methods of preparing a liposome from the ladderane lipids disclosed herein, and compositions thereof. Aspects of the invention include encapsulated one or more cargo moieties in the liposome or compositions thereof and use of the subject liposome compositions as vehicles in drug delivery, imaging, diagnostics and other medical applications. Aspects of the methods disclosed herein include administering a liposomal composition comprising a pharmaceutical agent to a subject under conditions sufficient to deliver the composition to a site of interest in the subject, and release the pharmaceutical agent from the liposomal composition.

Methods for preparing a variety of ladderane precursors, ladderane compounds and ladderane lipids are provided. Also provided are methods of preparing a liposome from the ladderane lipids disclosed herein, and compositions thereof. Aspects of the invention include encapsulated one or more cargo moieties in the liposome or compositions thereof and use of the subject liposome compositions as vehicles in drug delivery, imaging, diagnostics and other medical applications. Aspects of the methods disclosed herein include administering a liposomal composition comprising a pharmaceutical agent to a subject under conditions sufficient to deliver the composition to a site of interest in the subject, and release the pharmaceutical agent from the liposomal composition.

Methods for preparing a variety of ladderane precursors, ladderane compounds and ladderane lipids are provided. Also provided are methods of preparing a liposome from the ladderane lipids disclosed herein, and compositions thereof. Aspects of the invention include encapsulated one or more cargo moieties in the liposome or compositions thereof and use of the subject liposome compositions as vehicles in drug delivery, imaging, diagnostics and other medical applications. Aspects of the methods disclosed herein include administering a liposomal composition comprising a pharmaceutical agent to a subject under conditions sufficient to deliver the composition to a site of interest in the subject, and release the pharmaceutical agent from the liposomal composition.

Provided herein are convenient and efficient processes for preparing (2E,6Z)-2,6-nonadienal and (2E)-6,7-epoxy-2-nonenal with a reduced number of steps. For instance, provided herein is a process for preparing (2E,6Z)-2,6-nonadienal, including at least steps of subjecting a (6,6-dialkoxy-4-hexenylidene)triarylphosphorane compound of the general formula: Ar.sub.3PCH(CH.sub.2).sub.2CHCHCH(OR.sup.1)(OR.sup.2) to a Witting reaction with propanal to form a 1,1-dialkoxy-(6Z)-2,6-nonadiene compound of the general formula (6); and subjecting the 1,1-dialkoxy-(6Z)-2,6-nonadiene compound to hydrolysis to form (2E,6Z)-2,6-nonadienal. Also provided is a process for preparing (2E)-cis-6,7-epoxy-2-nonenal of the formula (8), comprising a step of subjecting (2E,6Z)-2,6-nonadienal thus obtained to epoxidation to form (2E)-cis-6,7-epoxy-2-nonenal. ##STR00001##

Provided herein are convenient and efficient processes for preparing (2E,6Z)-2,6-nonadienal and (2E)-6,7-epoxy-2-nonenal with a reduced number of steps. For instance, provided herein is a process for preparing (2E,6Z)-2,6-nonadienal, including at least steps of subjecting a (6,6-dialkoxy-4-hexenylidene)triarylphosphorane compound of the general formula: Ar.sub.3PCH(CH.sub.2).sub.2CHCHCH(OR.sup.1)(OR.sup.2) to a Witting reaction with propanal to form a 1,1-dialkoxy-(6Z)-2,6-nonadiene compound of the general formula (6); and subjecting the 1,1-dialkoxy-(6Z)-2,6-nonadiene compound to hydrolysis to form (2E,6Z)-2,6-nonadienal. Also provided is a process for preparing (2E)-cis-6,7-epoxy-2-nonenal of the formula (8), comprising a step of subjecting (2E,6Z)-2,6-nonadienal thus obtained to epoxidation to form (2E)-cis-6,7-epoxy-2-nonenal. ##STR00001##

The present invention relates to compounds of formula (I): ##STR00001##
in which R1 is a hydrogen atom, a phenyl radical, or a straight or branched, saturated or unsaturated hydrocarbon radical having 1 to 8 carbon atoms.