CAS: 127-41-3; (E)-4-(2,6,6-Trimethylcyclohex-2-En-1-yl)But-3-En-2-One

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专利信息

专利号:US-8222458-B2
优先权日:2008-06-13
标题 :Process or synthesis of (3S)- and (3R)-3-hydroxy-beta-ionone, and their transformation to zeaxanthin and beta-cryptoxanthin
发明人：KHACHIK FREDERICK; CHANG AN-NI
权利人:KHACHIK FREDERICK; CHANG AN-NI; UNIV MARYLAND
摘要:Disclosed is a process for the synthesis of (3R)-3-hydroxy-β-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-α-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-α-ionone ketal that was prepared from (rac)-α-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-α-ionone ketal followed by deprotection, lead to 3-hydroxy-α-ionone that was transformed into (rac)-3-hydrox-β-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-α-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-β-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(β-ionylideneethyl)triphenylphosphonium chloride [(3R)-C 15 -Wittig salt] and its (3S)-enantiomer [(3S)-C 15 -Wittig salt] according to known procedures. Double Wittig condensation of these Wittig salts with commercial available 2,5- dimethtylocta-2,4,6-triene-1,8-dial provided all 3 stereoisomers of zeaxanthin. Similarly, (3R)-C 15 -Wittig and its (3S)-enantiomer were each coupled with β-apo-12′-carotenal.

专利号:US-7858828-B2
优先权日:2008-03-26
标 题 :Process for synthesis of (3R,3'R,6'R)-lutein and its stereoisomers
发明人：KHACHIK FREDERICK; CHANG AN-NI
权利人:UNIV MARYLAND
摘要:(3R,3′R,6′R)-Lutein and (3R,3′R)-zeaxanthin are two dietary carotenoids that are present in most fruits and vegetables commonly consumed in the US. These carotenoids accumulate in the human plasma, major organs, and ocular tissues. In the past decade, numerous epidemiological and experimental studies have shown that lutein and zeaxanthin play an important role in the prevention of age-related macular degeneration (AMD) that is the leading cause of blindness in the U.S. and Western World. The invention provides a process for the synthesis of (3R,3′R,6′R)-lutein and its stereoisomers from commercially available (rac)-α-ionone by a C 15 +C 10 +C 15 coupling strategy. In addition, the present invention also provides access to the precursors of optically active carotenoids with 3-hydroxy-ε-end group that are otherwise difficult to synthesize. The process developed for the synthesis of lutein and its stereoisomers is straightforward and has potential for commercialization.

专利号:US-2024240209-A1
优先权日:2021-04-20
标 题:Synthesis of enantiopure cis-a-irone from a renewable carbon source
发明人：CHEN XIXIAN; ZHANG CONGQIANG; T REHKA; SHUKAL SUDHA; SMITH DEREK; ANDRÉ ISABELLE; JEREMY ESQUE
权利人:AGENCY SCIENCE TECH & RES; INSTITUT NATIONAL DE RECH POUR L AGRICULTURE LALIMENTATION ET LENVIRONMENT; CENTRE NAT RECH SCIENT; INSTITUT NAT DES SCIENCES APPLIQUEES DE TOULOUSE
摘要:Synthesis of enantiopure cis-α-irone from a renewable carbon source Disclosed herein are natural and synthetic enzymes capable of performing a method of producing cis-α-irone. The method comprises providing an enzyme capable of converting psi-ionone to cis-α-irone; and contacting the enzyme and psi-ionone under suitable conditions to produce cis-α-irone. The enzyme may be a methyltransferase from Streptomyces albireticuli (SaMT), a promiscuous bifunctional methyltransferase/cyclase (pMT1) enzyme from Streptomyces, or a modified pMT1 enzyme with at least one substitution. The enzymes allow the in-vivo and in-vitro production of cis-α-irone including the use of glucose as feedstock for the biotransformation into cis-α-irone.

专利号:US-11124809-B2
优先权日:2017-12-21
标题 :Production of alpha-(R)-(E)-(+)-ionone in recombinant Saccharomyces cerevisiae
发明人：AGOSIN TRUMPER EDUARDO ESTEBAN; SAITUA PEREZ FRANCISCO JAVIER; LOPEZ SALINAS JAVIERA CECILIA; DOMARADZKI MACIEJ E; IBACETA ACEVEDO MAXIMILIANO; ARENAS FRIGOLETT NATALIA
权利人:CENTROME INC
摘要:This invention provides improved biological synthesis of the apocarotenoid α-ionone in Saccharomyces cerevisiae. The final native step involved in the natural apocarotenoid pathway depends on an endogenous farnesyl pyrophosphate synthase (FPPs). From there, heterologous geranylgeranyl pyrophosphate synthase (crtE), phytoene synthase (crtB), phytoene desaturase (crtI), lycopene ε-cyclase (LycE) and a Carotenoid Cleavage Dioxygenase (CCD1) are required to complete the synthesis of α-ionone. Lycopene ε-cyclase from lettuce (Lactuca sativa) or modified cyclase from Arabidopsis thaliana was used to overproduce lycopene which was then cleaved by the carotenoid cleavage dioxygenase from Petunia hybrida (Ph-CCD1).

专利号:US-7084281-B2
优先权日:2003-01-22
标题:Synthesis of dihalohydrins and tri- and tetra-substituted olefins
发明人：FALCK JOHN R; BARMA DEB K; KUNDU ABHIJIT
权利人:UNIV TEXAS
摘要:A novel synthesis reaction for highly stereospecific tri- and tetra-substituted olefins is described. A single stereoisomer of stable α-halo-α,β-ester is produced in high yield by the reaction of aldehyde or ketone with a trihalogenated compound such as trichloroacetate in the presence of CrCl 2 in a solvent. By varying the amount of CrCl 2 used, the stable dihalohydrin intermediate may be obtained as well.

专利号:US-9458021-B2
优先权日:2013-07-27
标 题 :Sol-gel method for synthesis of nano-porous carbon
发明人：MITRA SHANTANU
权利人:FARAD POWER INC
摘要:The present patent application discloses a novel sol-gel process to synthesize a nano-porous solid carbon material—suitable for use in electrodes in energy storage applications—from a combination of liquid reagents that undergo a polymerization reaction to form a matrix.