176506-97-1

Upstream product

• 15205-57-9 tribenzyl phosphite 

Downstream Products

• 26292-51-3 dibenzyl methyl phosphate 
• 174648-17-0 3-acetoxy-2,2-dimethoxypropyl dibenzyl phosphate 
• 798554-50-4 (2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate 
• 819862-89-0 3-hydroxy-2,2-dimethoxypropyl dibenzyl phosphate 
• 258518-29-5 2,3-O-isopropylidene-2-C-methyl-D-erythrose-(O-benzyl)oxime 4-dibenzyl phosphate 
• 1356384-01-4 N-Cbz-5-(S)-dibenzylphosphate-(S)-tert-butylpipecolate 
• 1356383-47-5 N-Cbz-5-(R)-dibenzylphosphate-(S)-tert-butylpipecolate 
• 914359-41-4 C₄₇H₆₄O₈P₂ 
• 914359-40-3 C₆₁H₇₆O₈P₂ 
• 882491-48-7 C₆₈H₈₂O₈P₂ 
• 258518-31-9 2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate 
• 258518-30-8 2,3-O-isopropylidene-2-C-methyl-D-erythrose 4-dibenzyl phosphate 
• 541513-95-5 (2R,3S,5S)-6-bis(benzyloxy)phosphoryloxy-2-methyl-3,5-bis(tetrahydropyran-2-yloxy)hexanoic acid benzyl ester 
• 541513-79-5 (2R,3S,5S)-3,5-diacetoxy-6-bis(benzyloxy)phosphoryloxy-2-methylhexanoic acid benzyl ester 

Relevant academic research and scientific papers

Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates

A method for synthesizing intermediates for use in the synthesis of carotenoid synthetic intermediates, carotenoid analogs, and/or carotenoid derivatives. The carotenoid analog, derivative, or intermediate may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include methods for synthesizing chemical compounds including an analog or derivative of a carotenoid. Carotenoid analogs or derivatives may include acyclic end groups. In some embodiments, a carotenoid analog or derivative may include at least one substituent. The substituent may enhance the solubility of the carotenoid analog or derivative such that the carotenoid analog or derivative at least partially dissolves in water.

Use of carotenoids and/or carotenoid derivatives/analogs for reduction/inhibition of certain negative effects of COX inhibitors

Administering carotenoids, and in particular xanthophyll carotenoids, or analogs or derivatives of astaxanthin, lutein, zeaxanthin, lycoxanthin, lycophyll, or lycopene to a subject undergoing treatment with COX-2 inhibitor drugs may reduce at least a portion of the adverse side effects associated with administration of COX-2 selective inhibitor drugs. The carotenoids, or analogs or derivatives thereof may be administered to a subject prior to, at the same time as, or after the commencement of COX-2 selective inhibitor drug therapy. The carotenoids, or analogs or derivatives thereof may be administered to a subject concurrently with COX-2 selective inhibitor drugs therapy. The carotenoids, or analogs or derivatives thereof may be incorporated into pharmaceutical preparation in combination with the COX-2 selective inhibitor drug or may be administered separately. Administration of the analogs or derivatives described herein may reduce peroxidation of LDL and other lipids in the serum and plasma cell membranes of subjects undergoing COX-2 selective inhibitor drug therapy. Administration of the analogs or derivatives described herein may reduce the incidence of deleterious clinical cardiovascular events undergoing COX-2 selective inhibitor drug therapy.

The synthesis and aqueous superoxide anion scavenging of water-dispersible lutein esters

Xanthophyll carotenoids of the C40 series, which includes commercially important compounds such as lutein, zeaxanthin, and astaxanthin, have poor aqueous solubility in the native state. Hawaii Biotech, Inc. (HBI) and others have shown that the aqueous dispersibility of derivatized carotenoids can be increased by varying the chemical structure of the esterified moieties. In the current study, the published series of novel, highly water-dispersible C40 carotenoid derivatives has been extended to include (3R,3′R,6′R)- lutein (β,ε-carotene-3,3′-diol) derivatives. Two novel derivatives were synthesized by esterification with inorganic phosphate and succinic acid, respectively, and subsequently converted to the sodium salts. Red-orange, clear, aqueous suspensions were obtained after addition of these novel derivatives to USP-purified water. Aqueous dispersibility of the disuccinate sodium salt of lutein was 2.85 mg/mL; the diphosphate salt demonstrated a >10-fold increase in dispersibility at 29.27 mg/mL. As reported previously, these aqueous suspensions were obtained without the addition of heat, detergents, co-solvents, or other additives. The direct aqueous superoxide scavenging abilities of these novel derivatives were subsequently evaluated by electron paramagnetic resonance (EPR) spectroscopy in a well-characterized in vitro isolated human neutrophil assay. The novel derivatives were nearly identical aqueous-phase scavengers, demonstrating dose-dependent suppression of the superoxide anion signal (as detected by spin-trap adducts of DEPMPO) in the millimolar range. These lutein-based soft drugs will likely find utility in those commercial and clinical applications for which aqueous-phase singlet oxygen quenching and direct radical scavenging may be required.

WATER-DISPERSIBLE CAROTENOIDS, INCLUDING ANALOGS AND DERIVATIVES

A chemical composition; comprising one or more carotenoid analogs or derivatives having a structure (I), (II) and (III) where each R3 is independently hydrogen or methyl, and where each R1 and R2 are independently wherein each R5 is independently hydrogen, -OH, or -OR6, wherein at least one R5 group is -OR6; wherein each R6 is independently: alkyl; aryl; -alkyl-N(R7)2; -aryl-N(R7)2; -alkyl-N+ (R7)3; -aryl-N+(R7)3; -alkyl-CO2R7; -aryl-CO2R7; -alkyl-CO2; -aryl-CO2; -CO2R8; -P(O)(OR8)2; -S(O)(OR8)2; an amino acid; a peptide, a carbohydrate; -C(O)- (CH2)0-CO2R9; a nucleoside residue, or a co-antioxidant; wherein R7 is hydrogen, alkyl, or aryl; wherein R8 is hydrogen, alkyl, aryl, benzyl or a co-antioxidant; wherein R9 is hydrogen; alkyl; aryl; -P(0)(OR8)2; -S(0)(OR8)2; an amino acid; a peptide, a carbohydrate; a nucleoside, or a co-antioxidant; and wherein n is 1 to 9. The compounds are useful for the inhibition and amelioration of diseases resulting in change and/or loss of vision.

Reduction in complement activation and inflammation during tissue injury by carotenoids, carotenoid analogs, or derivatives thereof

Administering water-soluble or dispersible synthetic analogs or derivatives of astaxanthin, lutein, zeaxanthin, or lycophyll and/or other carotenoids to a subject may reduce some of the adverse effects of inflammation in a body organ or tissue. The analogs or derivatives may be incorporated into pharmaceutical, over-the-counter, or nutraceutical preparations. Administration of the analogs or derivatives described herein may reduce deposition of inflammatory mediators such as C-reactive protein, complement system proteins or the membrane attack complex (MAC) in tissues. Reduced deposition of these molecules in tissues may reduce cell damage and/or lysis in the tissues.

CAROTENOIDS, CAROTENOID ANALOGS, OR CAROTENOID DERIVATIVES FOR THE TREATMENT OF PROLIFERATIVE DISORDERS

A method and system used for treating proliferative disorders using carotenoids, carotenoid analogs, and/or carotenoid derivatives. The method and system may be used for chemoprevention and/or chemotherapy. The method and system may induce apoptosis in target cells, tissues, and/or organs. The analog, derivative, or intermediate may be administered to a cell, a group of cells, a tissue, an organ or a subject, such that at least a portion of the undesirable consequences of the proliferative disorder are thereby reduced.

METHODS FOR SYNTHESIS OF CHIRAL INTERMEDIATES OF CAROTENOIDS, CAROTENOID ANALOGS, AND CAROTENOID DERIVATIVES

A method used for synthesizing intermediates for use in the synthesis of carotenoids and carotenoid analogs, and/or carotenoid derivatives. In some embodiments, the invention includes methods for synthesizing optically active intermediates useful for the synthesis of optically active carotenoids.

Carotenoids, carotenoid analogs, or carotenoid derivatives for the treatment of visual disabilities

A method and system used for treating visual disabilities using carotenoids, carotenoid analogs, and/or carotenoid derivatives. The analog, derivative, or intermediate may be administered such that a subject's risk of experiencing diseases associated with visual disabilities may be thereby reduced. Analogs or derivatives of carotenoids may include substituents including for example co-antioxidants (e.g., Vitamin C and Vitamin C analogs). The carotenoid analog or derivative may be synthetic. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include an acyclic alkene including at least one substituent and/or a cyclic ring including at least one substituent. In some embodiments, a carotenoid analog or derivative may include at least one substituent. The substituent may enhance the solubility of the carotenoid analog or derivative such that the carotenoid analog or derivative at least partially dissolves in water.

Synthesis and evaluation of 1-deoxy-D-xylulose 5-phosphate analogues as chelation-based inhibitors of methylerythritol phosphate synthase

A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and a

CAROTENOID ANALOGS OR DERIVATIVES FOR THE INHIBITION AND AMELIORATION OF INFLAMMATION

A method for inhibiting and/or ameliorating the occurrence of diseases in a human subject whereby a subject is administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative. In some embodiments, the administration of analogs or derivatives of carotenoids may inhibit and/or ameliorate the occurrence of diseases in subjects. In some embodiments, analogs or derivatives of carotenoids may be water-soluble and/or water dispersible. Maladies that may be treated with analogs or derivatives of carotenoids embodied herein may include diseases that provoke or trigger an inflammatory response. In an embodiment, asthma may be treated with analogs or derivatives of carotenoids embodied herein. In an embodiment, administering analogs or derivatives of carotenoids embodied herein to a subject may control or affect the bioavailability of eicosanoids. In an embodiment, atherosclerosis may be treated with analogs or derivatives of carotenoids embodied herein. In an embodiment, administering the analogs or derivatives of carotenoids embodied herein to a subject may control or affect the bioavailability of 5-LO-catalyzed eicosanoid metabolites. In an embodiment, 5-LO-catalyzed eicosanoid metabolites that may be controlled or affected by administering analogs or derivatives of carotenoids to a subject may include proinflammatory effector molecules (e.g., leukotrienes).