- Efficient syntheses of C20-carotene and crocetin (descrocetin) esters promoted by an acidic ionic liquid
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Efficient syntheses of C20-carotene and crocetin or descrocetin esters from fumaraldehyde bis-dimethylacetal are described. The key steps of these syntheses are the reactions of fumaraldehyde and (2E,4E,6E)-octa-2,4,6- trienedial bis-dimethylac
- Kryshtal, Galina V.,Zhdankina, Galina M.,Zlotin, Sergei G.,Ignat'Ev, Nikolai V.,Schulte, Michael
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- METHODS OF SYNTHESIZING CAROTENOIDS
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Provided herein novel processes for preparing carotenoids, substantially pure carotenoids (such as substantially pure trans crocetin diesters and substantially pure trans sodium crocetinate), pharmaceutical compositions, and related methods of treatment and uses. The provided compositions have uses in treating diseases, disorders and conditions associated with, but not limited to, infection, ARDS, endotoxemia, inflammation, sepsis, ischemia, hypoxia, shock, stroke, lung injury, wound healing, traumatic injury, reperfusion injury, cardiovascular disease, kidney disease, liver disease, inflammatory disease, metabolic disease, pulmonary disorders, blood related disorders and hyperproliferative diseases such as cancer. Methods of making, and using the aqueous solutions and pharmaceutical compositions are also provided.
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Paragraph 0169-0176
(2021/10/15)
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- REGULATING PLANT GROWTH USING A DIAPOCAROTENOID
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Embodiments of the present disclosure describe diapocarotenoid plant growth regulators represented by formula (I): R-A-R (I) or a precursor, salt, solvate, stereoisomer or polymorph thereof; wherein R is a monovalent carbonyl moiety selected from the group consisting of aldehydes, ethers, diethers, carboxylic acids, alcohols, and ester carboxylates and A is a bivalent polyene represented by the bivalent moiety -(CRa=CRb)x- wherein x is the number of double bonds in polyene moiety A, and Ra and Rb are, independently, hydrogen, a hydrocarbon, or an alkoxy group, and composition of the diapocarotenoid plant growth regulators in an agronomically acceptable carrier. Methods of regulating plant growth including promoting root development, increasing nutrient uptake, enhancing resistance to abiotic stress factors, invigorating plant growth, increasing plant yield, and increasing plant biomass by applying at least one diapocarotenoid plant growth regulator to a seed, plant propagation material, plant or plant growth medium are also described.
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Paragraph 00119
(2019/10/15)
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- BIPOLAR TRANS CAROTENOID SALTS AND USES THEREOF
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PROBLEM TO BE SOLVED: To provide compounds useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans. SOLUTION: There is provided a compound which has a structure represented by YZ-TCRO-ZY and is not trans sodium crocetinate [where, Y is a cation; Z is a polar group which is associated with the cation; and TCRO is trans carotenoid skeleton], and preferably, Y is a monovalent metal ion selected from the group consisting of Na+, K+ and Li+, or is an organic cation selected from the group consisting of R4 N+ and R3S+ [R is H, or CnH2n+1(n is 1 to 10)]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
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Paragraph 0083; 0097; 0131; 0132; 0133
(2018/10/26)
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- Preparation method of 2,7-dimethyl-2,4,6-octatriene-1,8-dial
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The invention discloses a preparation method of 2,7-dimethyl-2,4,6-octatriene-1,8-dial. The preparation method comprises the following steps: a) reacting 1,4-dibromo-2-buten as shown in a formula II with magnesium to obtain a Grignard reagent as shown in a formula III; b) reacting the Grignard reagent as shown in the formula III with ethylene oxide as shown in a formula IV, and performing acidolysis to obtain a compound V; c) performing an oxidation reaction on the compound V to obtain a compound VI; d) performing an aldol condensation reaction on the compound VI and formaldehyde to obtain a compound VII; and e) performing a hydroisomerization reaction on the compound VII to obtain 2,7-dimethyl-2,4,6-octatriene-1,8-dial as shown in a formula I, wherein the reaction equation is shown in thedescription. The preparation method has the advantages that the raw materials are easy to get, the reaction yield is high, the process is simple, and the industrial production is facilitated.
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Paragraph 0059; 0060; 0061
(2018/11/22)
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- Characterization of the Saffron Derivative Crocetin as an Inhibitor of Human Lactate Dehydrogenase 5 in the Antiglycolytic Approach against Cancer
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Inhibition of lactate dehydrogenase (LDH) represents an innovative approach to tackle cancer because this peculiar glycolytic metabolism is characteristic of most invasive tumor cells. An investigation into the biological properties of saffron extracts led to the discover of their LDH-inhibition properties. In particular, the most important saffron components, crocetin, was found to inhibit LDH (IC50 = 54.9 ± 4.7 μM). This carotenoid was independently produced by chemical synthesis, and its LDH-inhibition properties manifested via its antiproliferative activity against two glycolytic cancer cell lines (A549 and HeLa, IC50 = 114.0 ± 8.0 and 113.0 ± 11.1 μM, respectively). The results described in this article suggest that saffron may be a helpful alimentary component in the prevention of cancer that potentially contributes to the efficacy of approved cancer therapies.
- Granchi, Carlotta,Fortunato, Serena,Meini, Serena,Rizzolio, Flavio,Caligiuri, Isabella,Tuccinardi, Tiziano,Lee, Hyang Yeon,Hergenrother, Paul J.,Minutolo, Filippo
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p. 5639 - 5649
(2017/07/26)
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- BIPOLAR TRANS CAROTENOID SALTS AND THEIR USE
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PROBLEM TO BE SOLVED: To provide trans carotenoid salt compounds useful for improving the diffusibility of oxygen between red blood cells and a body tissue in mammalian including human being, a method for producing them, a method for solubilizing them, and a method for using them. SOLUTION: There are provided compounds represented by the following formula, and are compounds not being trans sodium crocetinate: YZ-TCRO-ZY[Y denotes a cation; Z denotes a polar group coupled to the cation; TCRO denotes a trans carotenoid skeleton; preferably, as follows; Y denotes the monovalent metal ion of Na+,K+ or Li+ or R4 N+ or R3S+;R denotes H or CnH2n+1;n denotes the integer of 1 to 10;Z denotes a carboxyl group, a sulfuric acid group, a mono-phosphoric acid group, a di-phosphoric acid group, or a tri-phosphoric acid group; and TCRO denotes a group using isopronoid in which the single bond and double bond of straight chain carbon and carbon as exemplified by the following formula is repeated (X respectively independently denotes H, a straight chain/branched carbon chain substituted/non-substituted with 1 to 10C halogen or a halogen)]. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT
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Paragraph 0097; 0131-0134
(2018/10/31)
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- Synthesis of labile all-trans-7,8,7′,8′-bis-acetylenic carotenoids by bi-directional Horner-Wadsworth-Emmons condensation
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A new stereoselective synthesis of the C40-bis-acetylenic carotenoids all-trans-(3R,3′R)-alloxanthin and all-trans-3,4,7,8,3′,4′,7′,8′-octadehydro-β,β-carotene, both compounds featuring a stereochemically labile C7-C10 enyne, based on a bi-directional Horner-Wadsworth-Emmons (HWE) reaction of a C15-phosphonate and a central C10-dialdehyde, is reported. The triene unit of the latter fragment was synthesized using the acyclic metathesis/dimerization reaction.
- Vaz, Belén,Fontán, Noelia,Casti?eira, Marta,álvarez, Rosana,De Lera, ángel R.
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supporting information
p. 3024 - 3031
(2015/03/18)
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- Synthesis and characterization of quantum dot nanoparticles bound to the plant volatile precursor of hydroxy-apo-10′-carotenal
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This study is focused on the synthesis and characterization of hydroxy-apo-10′-carotenal/quantum dot (QD) conjugates aiming at the in vivo visualization of β-ionone, a carotenoid-derived volatile compound known for its important contribution to the flavor and aroma of many fruits, vegetables, and plants. The synthesis of nanoparticles bound to plant volatile precursors was achieved via coupling reaction of the QD to C27- aldehyde which was prepared from α-ionone via 12 steps in 2.4% overall yield. The formation of the QD-conjugate was confirmed by measuring its fluorescence spectrum to observe the occurrence of fluorescence resonance energy transfer.
- Tu, Vo Anh,Kaga, Atsushi,Gericke, Karl-Heinz,Watanabe, Naoharu,Narumi, Tetsuo,Toda, Mitsuo,Brueckner, Bernhard,Baldermann, Susanne,Mase, Nobuyuki
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p. 6808 - 6815
(2014/08/18)
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- METHOD FOR SYNTHESIZING 2,7-DIMETHYL-2,4,6-OCTATRIENE-1,8-DIALDEHYDE
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Provided in the present invention is a method for synthesizing 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde. The synthesis method comprises the following steps: (1) adding acetaldehyde diethyl acetal and ethyl-(1-propenyl)-ether under the effect of a catalyst to produce 1,1,3-triethoxy-2-methyl-butane; (2) pyrolysis synthesizing 1,1,3-triethoxy-2-methyl-butane under the catalytic effects of isoquinoline and p-Toluenesulfonic acid to produce 1-methoxy-2-methyl-1,3-butadiene; (3) dissolving 1-methoxy-2-methyl-1,3-butadiene in anhydrous ethanol solvent for synthesis with a phase transfer catalyst, cetyl-trimethyl ammonium bromide, and a chlorinating agent, trichloroisocyanuric acid, to generate 4,4-diethoxy-3-methyl-1-chloro-butene; (4) combining 4,4-diethoxy-3-methyl-1-chloro-butene with a triphenylphosphine salt to produce a phosphonium salt; and (5) condensing the phosphonium salt under the effects of hydrogen peroxide in conjunction with sodium carbonate solution to generate 1,1,8,8-tetramethyl-2,7-dimethyl-2,4,6-octatriene; then hydrolyzing under acidic conditions to synthesize 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde. The present invention has a simple process route, is easy to operate, and has mild conditions, great yield, and great industrial value.
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Paragraph 0033
(2015/01/07)
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- METHOD FOR SYNTHESIZING 2,7-DIMETHYL-2,4,6-OCTATRIENE-1,8-DIALDEHYDE
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Provided in the present invention is a method for synthesizing 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde. The synthesis method comprises the following steps: (1) adding acetaldehyde diethyl acetal and ethyl-(1-propenyl)-ether under the effect of a catalyst to produce 1,1,3-triethoxy-2-methyl-butane; (2) pyrolysis synthesizing 1,1,3-triethoxy-2-methyl-butane under the catalytic effects of isoquinoline and p-Toluenesulfonic acid to produce 1-methoxy-2-methyl-1,3-butadiene; (3) dissolving 1-methoxy-2-methyl-1,3-butadiene in anhydrous ethanol solvent for synthesis with a phase transfer catalyst, cetyl-trimethyl ammonium bromide, and a chlorinating agent, trichloroisocyanuric acid, to generate 4,4-diethoxy-3-methyl-1- chloro-butene; (4) combining 4,4-diethoxy-3-methyl-1-chloro-butene with a triphenylphosphine salt to produce a phosphonium salt; and (5) condensing the phosphonium salt under the effects of hydrogen peroxide in conjunction with sodium carbonate solution to generate 1,1,8,8-tetramethyl-2,7-dimethyl-2,4,6-octatriene; then hydrolyzing under acidic conditions to synthesize 2,7-dimethyl-2,4,6-octatriene-1,8- dialdehyde. The present invention has a simple process route, is easy to operate, and has mild conditions, great yield, and great industrial value.
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- BIPOLAR TRANS CAROTENOID SALTS AND THEIR USES
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The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.
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Page/Page column 31-32
(2008/06/13)
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- METHOD FOR PRODUCING 2,7-DIMETHYL-OCTA-2,4,6-TRIENEDIAL
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The invention relates to an improved method for producing 2,7-dimethyl-octa-2,4,6-trienedial of formula (I), by: a) a double enol ether condensation of a butenedial bis-acetal of formula (II) with an enol ether of formula (III) in the presence of a Lewis acid catalyst to form a condensation product of formula (IV), the groups R1 and R2 of formulas (II) to (IV) independently of one another representing C1-C6 alkyl; b) a hydrolysis of the acetal groups of (IV) by the addition of an aqueous acid, forming the dialdehyde of formula (V); c) conversion of (V) into the dialdehyde (I) by reaction with an aqueous base; and d) crystallisation of (I) from the reaction mixture, whereby the steps (a) to (d) are carried out in the presence of an inert, organic solvent that is immiscible with water.
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Page/Page column 10
(2008/06/13)
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- γ-allenyl allyl benzothiazole sulfonyl anions undergo cis-selective (Sylvestre) Julia olefinations
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γ-Allenyl allyl benzothiazolyl sulfones 8 and ent-8 provided allenyl trienes and polyenes with cis-selectivities ranging from 71:29 to 100:0 upon condensation (NaHMDS, THF, -78 °C to 25 °C) with a variety of unsaturated aldehydes.
- Vaz, Belén,Alvarez, Rosana,Souto, José A.,De Lera, Angel R.
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p. 294 - 298
(2007/10/03)
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- Bipolar trans carotenoid salts and their uses
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The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.
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- Biopolar trans carotenoid salts and their uses
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The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.
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- Process for making β-carotene
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A process for preparing β-carotene, represented by Formula 3 staring from a sulfone compound of Formula B
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- Method of catalyzing condensation reactions
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Hydrogen bis(oxalato)borate of the formula STR1 is used as a protonic acid catalyst in condensation reactions, such as Friedel-Crafts condensations, vinyl ether condensations of acetals with vinyl or propenyl ethers and acylations of phenols. The products of such condensations are, for example, dihydro-vitamin K1 monobenzoate, d,l-α-tocopherol, various intermediates in the synthesis of carotenoids as well as d,l-α-tocopherol acetate. As a result of the use in accordance with the invention of hydrogen bis(oxalato)borate various disadvantages associated with the use of other protonic acid catalysts, e.g. problems with corrosion, toxicity and environmental contamination, are avoided. The novel catalyst has advantages with respect to selectivity, yields, amounts required as well as working up after completion of the respective condensation.
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- Synthesis of all-trans-beta-carotene retinoids and derivatives labelled with 14C
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In this paper we report the synthesis of all-trans Retinoic acid, Retinal, Retinol specifically labelled with 14C at position 7 and all-trans Beta-carotene labelled at positions 7 and 7′, with more than 98% radiochemical purity. All products were obtained with about 15% overall yield from 14C sodium cyanide.
- Azim, El-Mostafa,Auzeloux, Philippe,Maurizis, Jean-Claude,Braesco, Veronique,Grolier, Pascal,Veyre, Annie,Madelmont, Jean-Claude
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p. 441 - 451
(2007/10/03)
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- Synthesis and characterization of all-E (12,12'-13C2)-, (13,13'-13C2)-, (14,14'-13C2)-, (15,15'-13C2)- and (20,20'-13C2)astaxanthin
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The all-E isomers of (12,12'-13C2)-, (13,13'-13C2)-, (14,14'-13C2)-, (15,15'-13C2)- and (20,20'-13C2)astaxanthin were prepared by total synthesis starting from commercially available 99percent 13C-enriched acetonitrile, acetic acid and methyl iodide.The astaxanthins were obtained in high purity and with high isotope incorporation (>99percent for every position).For this synthesis, the C15 + C10 + C15 strategy was used.The central C10-synthon, 2,7-dimethylocta-2,4,6-triene-1,8-dial, was symmetrically dilabelled at any position using two new synthetic schemes.The 13C2-enriched C10-dialdehydes were then converted in one step to the 13C2-enriched astaxanthins.
- Jansen, F. J. H. M.,Kwestro, M.,Schmitt, D.,Lugtenburg, J.
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p. 552 - 562
(2007/10/02)
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- Method of making 2,7-dimethyl-2,4,6-octatrienedial and derivatives thereof
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The present invention is an improved method to prepare 2,7-dimethyl-2,4,6-octatrienedial and related derivative compounds. This method of making 2,7-dimethyl-2,4,6-octatrienedial and derivatives thereof includes reacting 2-butenyl-bisphosphonic acid tetraalkyl ester and at least two equivalents of protected pyruvic aldehyde derivative in a nonpolar organic solvent in the presence of an alkali metal hydroxide. Compounds prepared by this invention are useful intermediates in the preparation of carotenoids.
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- Phosphonate reagent compositions
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Novel phosphonate compounds of the formula STR1 are disclosed and claimed, as well as methods for manufacturing the phosphonates from C-14 through C-16 aldehydes. The phosphonate compounds of the present invention can be employed to form 13-cis retinoic acid, retin-A and beta-carotene.
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- Synthese von optisch aktiven, natuerlichen Carotinoiden und strukturell verwandten Naturprodukten. IX. Synthese von (3R)-Hydroxyechinenon, (3R,3'R)- und (3R,3'S)-Adonixanthin, (3R)-Adonirubin, deren optischen Antipoden und verwandten Verbindungen
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The synthesis of racemic and optically active hydroxyechinenone (12-14), adonixanthin (16-19), adonirubin (22-24), meso-astaxanthin (26) and their corresponding diosphenols (15, 20, 21, 25, 27, 28, and 29) by Wittig reaction is reported, starting from suitable C15-phosphonium salts and C10-aldehydes.
- Bernhard, Kurt,Englert, Gerhard,Mayer, Hans,Mueller, Robert K.,Ruettimann, August,et al.
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p. 2469 - 2484
(2007/10/02)
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