50281-38-4

Usage

Uses

Used in Flavor and Fragrance Industry:
(3R)-3-Hydroxy-β-ionone is used as a key component in the synthesis of various fragrances and flavors due to its characteristic odor and taste. Its ability to mimic the scent and taste of natural compounds makes it a popular choice in the creation of artificial flavors and fragrances.
Used in Cosmetics and Personal Care Products:
(3R)-3-Hydroxy-β-ionone is used as a fixative in the cosmetics and personal care industry to enhance the longevity and stability of fragrances in products such as perfumes, lotions, and creams. Its ability to improve the overall sensory experience of these products makes it a valuable addition to their formulation.
Used in Pharmaceutical Applications:
(3R)-3-Hydroxy-β-ionone has potential applications in the pharmaceutical industry, where it can be used as a starting material for the synthesis of various drugs and drug candidates. Its unique chemical properties allow for the development of novel therapeutic agents with potential benefits in treating various health conditions.
Used in Research and Development:
(3R)-3-Hydroxy-β-ionone is also utilized in research and development settings, where it serves as a valuable tool for studying the properties and mechanisms of action of carotenoids and their derivatives. This knowledge can be applied to the development of new products and technologies in various industries, including agriculture, food science, and biotechnology.

Upstream product

• 1373498-16-8 isoxazoline 
• 118529-05-8 C₁₉H₃₄O₂Si 
• 1373498-18-0 C₁₁H₁₈O 
• 1373498-20-4 C₁₁H₁₈O 
• 1373498-21-5 C₁₇H₃₂OSi 
• 35849-64-0 3,3-dimethylpent-4-ynal 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 
• 54165-55-8 (3R)-3-Acetoxy-β-ionon 
• 42926-75-0 (4R)-4-hydroxy-2,6,6-trimethyl-1-cyclohexene-1-carbaldehyde 
• 67-64-1 acetone 
• 144-68-3 zeaxanthin 
• 1200125-02-5 (rac)-(E)-4-(4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-2,2-ethylenedioxy-3-butene 
• 14398-37-9 (E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal 
• 127-41-3 alpha-ionone 

Downstream Products

• 117596-89-1 4-<(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl>butan-2-one 
• 83021-07-2 (S,E)-4-[4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one 
• 54165-55-8 (3R)-3-Acetoxy-β-ionon 
• 260244-82-4 C₄₇H₄₆O₁₁ 
• 83021-09-4 (-)-3-<(R)-4-(t-Butyl)dimethylsilyloxy-2,6,6-trimethyl-1-cyclohexen-1-yl>propen-1-ol 
• 83021-10-7 (-)-<(R)-4-t-Butyldimethylsilyloxy-2,6,6-trimethyl-1-cyclohexen-1-yl>propenal 
• 83021-08-3 (-)-3-<(R)-4-t-Butyldimethylsilyloxy-2,6,6-trimethyl-1-cyclohexen-1-yl>propensaeure 
• 83021-15-2 (R)-3-(t-Butyl)dimethylsilyloxy-19,20-dinor-vitamin-A-aldehyd 
• 83021-13-0 (R)-3-(t-Butyl)dimethylsilyloxy-9,20-dinor-vitamin-A 
• 83021-11-8 (R)-3-(t-Butyl)dimethylsilyloxy-19,20-dinor-vitamin-A-saeureaethylester 
• 83021-17-4 (3R,3'R)-3,3'-Bis<(t-butyl)dimethylsilyloxy>-19,20,19'20-'tetranor-zeaxanthin 
• 650-69-1 (3R)-3-hydroxy-8'-apo-β-caroten-8'-al 
• 62742-02-3 (all-E)-(3R)-3-hydroxy-12'-apo-β-caroten-12'-al 
• 57593-78-9 (all-E,3R)-8'-apo-β-carotene-3,8'-diol 

Relevant academic research and scientific papers

Absolute configurational assignment of 3-hydroxycarotenoids

Attempts were made to develop an exciton chirality method applicable to the unique cases represented by 3-hydroxycarotenoids. However, this approach has so far not been successful. The 3-hydroxy configurations were therefore determined by the extended Mosher 1H-NMR method. Nine carotenoids with seven different end groups and of known 3-hydroxy configurations were derivatized with (R)- and (S)-methoxyphenylacetic acid (MPA); they all gave the expected shift differences. Three other auxiliary reagents with naphthalene and anthracene nuclei gave larger and consistent NMR shift differences, but they are not yet commercially available.

143. Citrus-Carotinoide. 2. Mitteilung. Synthese von (3R)-β-Citraurin, (3R)-β-Citraurol und (3R)-β-Citraurinin; Aufklaerung der Konfiguration von Citrus-Carotinoiden

(3R)-β-Citraurin, (3R)-β-citraurol and (3R)-β-citraurinene were prepared starting from (3R)-3-acetoxy-β-ionone.Comparison of the chiroptical data of β-citraurin from orange peels with those of the synthetic compound confirmed the 3R-configuration of the n

The human mitochondrial enzyme BCO2 exhibits catalytic activity toward carotenoids and apocarotenoids

The enzyme b-carotene oxygenase 2 (BCO2) converts carotenoids into more polar metabolites. Studies in mammals, fish, and birds revealed that BCO2 controls carotenoid homeostasis and is involved in the pathway for vitamin A production. However, it is controversial whether BCO2 function is conserved in humans, because of a 4-amino acid long insertion caused by a splice acceptor site polymorphism. We here show that human BCO2 splice variants, BCO2a and BCO2b, are expressed as pre-proteins with mitochondrial targeting sequence (MTS). The MTS of BCO2a directed a green fluorescent reporter protein to the mitochondria when expressed in ARPE-19 cells. Removal of the MTS increased solubility of BCO2a when expressed in Escherichia coli and rendered the recombinant protein enzymatically active. The expression of the enzymatically active recombinant human BCO2a was further improved by codon optimization and its fusion with maltose-binding protein. Introduction of the 4-amino acid insertion into mouse Bco2 did not impede the chimeric enzyme’s catalytic proficiency. We further showed that the chimeric BCO2 displayed broad substrate specificity and converted carotenoids into two ionones and a central C14-apocarotendial by oxidative cleavage reactions at C9,C10 and C9’,C10’. Thus, our study demonstrates that human BCO2 is a catalytically competent enzyme. Consequently, information on BCO2 becomes broadly applicable in human biology with important implications for the physiology of the eyes and other tissues.

Versatile amine-promoted mild methanolysis of 3,5-dinitrobenzoates and its application to the synthesis of Colorado potato beetle pheromone

A mild deacylation method for 3,5-dinitrobenzoates using methanolic solutions of amines, such as dialkylamines, was developed. The method’s versatility was confirmed by applying it to synthesizing a key intermediate for Colorado potato beetle pheromone.

The Oxidation of Hydrophobic Aromatic Substrates by Using a Variant of the P450 Monooxygenase CYP101B1

The cytochrome P450 monooxygenase CYP101B1, from a Novosphingobium bacterium is able to bind and oxidise aromatic substrates but at a lower activity and efficiency than norisoprenoids and monoterpenoid esters. Histidine 85 of CYP101B1 aligns with tyrosine 96 of CYP101A1, which, in the latter enzyme forms the only hydrophilic interaction with its substrate, camphor. The histidine residue of CYP101B1 was mutated to phenylalanine with the aim of improving the activity of the enzyme for hydrophobic substrates. The H85F mutant lowered the binding affinity and activity of the enzyme for β-ionone and altered the oxidation selectivity. This variant also showed enhanced affinity and activity towards alkylbenzenes, styrenes and methylnaphthalenes. For example the rate of product formation for acenaphthene oxidation was improved sixfold to 245 nmol per nmol CYP per min. Certain disubstituted naphthalenes and substrates, such as phenylcyclohexane and biphenyls, were oxidised with lower activity by the H85F variant. Variants at H85 (A and G) designed to introduce additional space into the active site so as to accommodate these larger substrates did not improve the oxidation activity. As the H85F mutant of CYP101B1 improved the oxidation of hydrophobic substrates, this residue is likely to be in the substrate binding pocket or the access channel of the enzyme. The side chain of the histidine might interact with the carbonyl groups of the favoured norisoprenoid substrates of CYP101B1.

Process or synthesis of (3S)- and (3R)-3-hydroxy-beta-ionone, and their transformation to zeaxanthin and beta-cryptoxanthin

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)-C15-Wittig salt] and its (3S)-enantiomer [(3S)-C15-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)-C15-Wittig and its (3S)-enantiomer were each coupled with β-apo-12′-carotenal.

Total synthesis of (±)-3-hydroxy-β-ionone through a ring-closing enyne metathesis

The total synthesis of (±)-3-hydroxy - ionone, a bisnor-sesquiterpene having allelopathic activity, has been accomplished employing an enyne metathesis for the construction of the C1-C8 segment and two-carbon elongation via a nitrile oxide-alkene [3+2] cycloaddition as the key steps. Georg Thieme Verlag Stuttgart · New York.

Synthesis of (3S)- and (3R)-3-hydroxy-β-ionone and their transformation into (3S)- and (3R)-β- cryptoxanthin

(3S)- and (3R)-3-Hydroxy-β-ionone and (3S)- and (3R)-3-Hydroxy-β- ionone synthesized in high enantiomeric purity from commercially available () - ionone. These ionones were then transformed into (3R) - cryptoxanthin and (3S) - cryptoxanthin by a C15+C10+C15 Wittig coupling strategy according to known methods. This methodology can considerably simplify the total synthesis of optically active carotenoids with 3-hydroxy - end groups that possess significant biological activities. Georg Thieme Verlag Stuttgart New York.

Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui

Twelve C13 nor-isoprenoids have been isolated from the leaves of Cestrum parqui (Solanaceae). The structure (2R,6R,9R)-2,9-dihydroxy-4- megastigmen-3-one has been assigned to the new compound. All the structures have been determined by spectros

Carotenoids and related polyenes. Part 9. Total synthesis of thermozeaxanthin and thermocryptoxanthin and the stabilizing effect of thermozeaxanthin on liposomes

Thermozeaxanthin and thermocryptoxanthin are efficiently synthesized via β-selective glucosidation of (3R)-3-hydroxy-β-ionone 7, and the stabilizing effects of zeaxanthin 5, its glucoside 3 and thermozeaxanthin-15 1a on liposomes are also examined.