Provided herein are tertiary amino ester derivatives of astaxanthin and methods of making the same and using the same, e.g., to improve inflammatory and/or cardiovascular health.

Provided herein are tertiary amino ester derivatives of astaxanthin and methods of making the same and using the same, e.g., to improve inflammatory and/or cardiovascular health.

The present invention provides a high-content carotenoid compound from Adonis amurensis. The content of the total carotenoid of the carotenoid compound is higher than 95%. The content of all-trans (3S, 3′S)-carotenoid is higher than 80%. The carotenoid crystals have a high purity, and can be used in multiple forms in the fields of a dietary supplement of a human being, a food additive, a feed additive and a cosmetic product. In addition, the present invention also provides a method for manufacturing the compound.

The present invention provides a high-content carotenoid compound from Adonis amurensis. The content of the total carotenoid of the carotenoid compound is higher than 95%. The content of all-trans (3S, 3′S)-carotenoid is higher than 80%. The carotenoid crystals have a high purity, and can be used in multiple forms in the fields of a dietary supplement of a human being, a food additive, a feed additive and a cosmetic product. In addition, the present invention also provides a method for manufacturing the compound.

The invention describes an environmentally friendly, sustainable and cost-effective method for preparing astaxanthin diesters of the formula 1, in which astaxanthin of the formula 2 is doubly esterified with fatty acid chlorides of the general formula 3. For this purpose, compound 2 and 3 are reacted in an organic solvent in the presence of a nitrogen-containing base of the general formula 4. The invention further relates to the non-therapeutic use of the diester 1, in which R is a residue selected from the group consisting of C13-C19-alkyl, C13-C19-alkenyl, C13-C19-alkdienyl and C13-C19-alktrienyl, in human or animal nutrition and also the therapeutic use of the diester 1 prepared according to the method as a medicament and also as an ingredient in a medicinal preparation.

The invention describes an environmentally friendly, sustainable and cost-effective method for preparing astaxanthin diesters of the formula 1, in which astaxanthin of the formula 2 is doubly esterified with fatty acid chlorides of the general formula 3. For this purpose, compound 2 and 3 are reacted in an organic solvent in the presence of a nitrogen-containing base of the general formula 4. The invention further relates to the non-therapeutic use of the diester 1, in which R is a residue selected from the group consisting of C13-C19-alkyl, C13-C19-alkenyl, C13-C19-alkdienyl and C13-C19-alktrienyl, in human or animal nutrition and also the therapeutic use of the diester 1 prepared according to the method as a medicament and also as an ingredient in a medicinal preparation.

The present invention relates to a process for purifying the xanthophylls astaxanthin and canthaxanthin.

The process comprises suspending the xanthophyll in an organic solvent or solvent mixture, treating the suspension of the xanthophyll in the organic solvent or solvent mixture at elevated temperature, and subsequent separation off of the xanthophyll from the solvent by a solid-liquid separation, wherein the organic solvent is selected from ketones of the general formula (I) and mixtures of ketones of the general formula (I)

##STR00001## where R.sup.1 is C.sub.1-C.sub.4 alkyl and R.sup.2 is selected from C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.8 cycloalkyl, phenyl and benzyl, wherein the phenyl rings in the two last-mentioned radicals are unsubstituted or can have 1 or 2 methyl groups, or R.sup.1 and R.sup.2 together are linear C.sub.4-C.sub.6 alkylene, which can bear 1, 2 or 3 methyl groups as substituents.

The present invention relates to a process for purifying the xanthophylls astaxanthin and canthaxanthin.

The process comprises suspending the xanthophyll in an organic solvent or solvent mixture, treating the suspension of the xanthophyll in the organic solvent or solvent mixture at elevated temperature, and subsequent separation off of the xanthophyll from the solvent by a solid-liquid separation, wherein the organic solvent is selected from ketones of the general formula (I) and mixtures of ketones of the general formula (I)

##STR00001## where R.sup.1 is C.sub.1-C.sub.4 alkyl and R.sup.2 is selected from C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.8 cycloalkyl, phenyl and benzyl, wherein the phenyl rings in the two last-mentioned radicals are unsubstituted or can have 1 or 2 methyl groups, or R.sup.1 and R.sup.2 together are linear C.sub.4-C.sub.6 alkylene, which can bear 1, 2 or 3 methyl groups as substituents.

The invention relates to a method for the non-stereoselective and also for the stereoselective synthesis of astaxanthin from astacin. For this purpose, a reducing agent is used selected from the group of hydrogen, a secondary alcohol, formic acid and also the salts of formic acid or from a mixture of at least two representatives of the compound classes stated above. The invention further relates to the use of astacin as starting compound for the synthesis of astaxanthin.

The invention relates to a method for the non-stereoselective and also for the stereoselective synthesis of astaxanthin from astacin. For this purpose, a reducing agent is used selected from the group of hydrogen, a secondary alcohol, formic acid and also the salts of formic acid or from a mixture of at least two representatives of the compound classes stated above. The invention further relates to the use of astacin as starting compound for the synthesis of astaxanthin.