- CORCHIOSIDE A, AN ORCINOL GLYCOSIDE FROM CURCULIGO ORCHIOIDES
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The rhizomes of Curculigo orchioides yielded hentriacontanol, sitosterol, stigmasterol, cycloartenol, sucrose and a new phenolic glycoside, named orchioside A (orcinol-3-β-D-xylopyranosyl-(1->6)β-D-glucopyranoside).The structure was elucidated by spectroscopic methods and chemical transformations. Key Word Index - Curculigo orchioides; Amaryllidaceae; corchioside A; orcinol glycoside.
- Garg, Shri N.,Misra, Laxmi N.,Agarwal, Santosh K.
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- COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING SWEET TASTE
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The present disclosure provides edible compositions comprising a flavor-grade sweet taste modulator or a combination of flavor-grade sweet taste modulators or a flavor-grade bitter taste blocker or a combination of flavor-grade bitter taste blockers of the present disclosure, food products comprising such edible compositions and methods of preparing such food products. The present disclosure also provides methods of reducing the amount of sugar in a food product, methods of reducing the caloric intake in a diet, and methods of enhancing sweet taste or blocking a bitter taste in a food product.
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Paragraph 0358; 0360
(2021/09/17)
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- Electrochemical-induced hydroxylation of aryl halides in the presence of Et3N in water
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A thorough study of mild and environmentally friendly electrochemical-induced hydroxylation of aryl halides without a catalyst is presented. The best protocol consists of hydroxylation of different aryl iodides and aryl bromides by water solution in the presence of Et3N under air, affording the target phenols in good isolated yields. Moreover, aryl chlorides were successfully employed as substrates. This methodology also provides a direct pathway for the formation of deoxyphomalone, which displayed a significant anti-proliferation effect.
- Ke, Fang,Lin, Chen,Lin, Mei,Long, Hua,Wu, Mei,Yang, Li,Zhuang, Qinglong
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supporting information
p. 6417 - 6421
(2021/08/03)
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- Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis
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The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.
- Maeda, Katsumi,Matsubara, Ryosuke,Hayashi, Masahiko
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supporting information
p. 1530 - 1534
(2021/03/08)
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- Method for synthesizing phenol or derivative thereof in aqueous phase by photocatalytic one-pot method
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The invention discloses a method for synthesizing phenol or a derivative thereof in an aqueous phase by a photocatalytic one-pot method. The method comprises the following steps: by taking a compoundaryl halide shown in formula (I) as a raw material and water as a solvent, adding a catalyst and an auxiliary agent, and carrying out reacting under the conditions of alkali and visible light to obtain the phenol or the derivative (II) thereof. Compared with the prior art, the method is applicable to a large number of functional groups, high in yield, few in byproducts, simple and safe to operate,low in cost and environmentally friendly, wherein R is selected from substituted or non-substituted phenyl, pyridyl, quinolyl or pyrimidinyl; X is selected from halogen; the substituted phenyl is substituted by C1-C4 alkyl, C1-C4 alkoxy, hydroxyl, halogen, cyano, aldehyde group, nitro, amino, acetyl or carboxyl; and the substituted pyridyl, quinolyl or pyrimidinyl is pyridyl, quinolyl or pyrimidinyl substituted by C1-C4 alkyl.
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Paragraph 0032-0033; 0074-0075; 0085-0106
(2020/12/08)
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- Mechanism and Structure of γ-Resorcylate Decarboxylase
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γ-Resorcylate decarboxylase (γ-RSD) has evolved to catalyze the reversible decarboxylation of 2,6-dihydroxybenzoate to resorcinol in a nonoxidative fashion. This enzyme is of significant interest because of its potential for the production of γ-resorcylate and other benzoic acid derivatives under environmentally sustainable conditions. Kinetic constants for the decarboxylation of 2,6-dihydroxybenzoate catalyzed by γ-RSD from Polaromonas sp. JS666 are reported, and the enzyme is shown to be active with 2,3-dihydroxybenzoate, 2,4,6-trihydroxybenzoate, and 2,6-dihydroxy-4-methylbenzoate. The three-dimensional structure of γ-RSD with the inhibitor 2-nitroresorcinol (2-NR) bound in the active site is reported. 2-NR is directly ligated to a Mn2+ bound in the active site, and the nitro substituent of the inhibitor is tilted significantly from the plane of the phenyl ring. The inhibitor exhibits a binding mode different from that of the substrate bound in the previously determined structure of γ-RSD from Rhizobium sp. MTP-10005. On the basis of the crystal structure of the enzyme from Polaromonas sp. JS666, complementary density functional calculations were performed to investigate the reaction mechanism. In the proposed reaction mechanism, γ-RSD binds 2,6-dihydroxybenzoate by direct coordination of the active site manganese ion to the carboxylate anion of the substrate and one of the adjacent phenolic oxygens. The enzyme subsequently catalyzes the transfer of a proton to C1 of γ-resorcylate prior to the actual decarboxylation step. The reaction mechanism proposed previously, based on the structure of γ-RSD from Rhizobium sp. MTP-10005, is shown to be associated with high energies and thus less likely to be correct.
- Sheng, Xiang,Patskovsky, Yury,Vladimirova, Anna,Bonanno, Jeffrey B.,Almo, Steven C.,Himo, Fahmi,Raushel, Frank M.
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p. 3167 - 3175
(2018/06/11)
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- Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes
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Novel 1,3-disulfonic acid imidazolium hydrogen sulfate, a halogen-free ionic liquid, is a recyclable and eco-benign catalyst for the trimethylsilyl protection of hydroxyl groups at room temperature under solvent free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-5 min). Deprotection of the resulting trimethylsilanes can also be achieved using the same catalyst in methanol. The catalyst was characterized by IR, 1H NMR, 13C NMR and MS studies. All the products were extensively characterized by IR, 1H NMR, MS, and elemental and melting point analyses. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered and reused for several times without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.
- Shirini, Farhad,Khaligh, Nader Ghaffari,Akbari-Dadamahaleh, Somayeh
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- Modifiable sulfur tethers as directing groups for aromatic C-H acetoxylation reactions
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A designed new class of modifiable sulfur tethers for aromatic C-H bond functionalizations is presented. As a model, the palladium-catalyzed directed acetoxylation reaction was studied. The more challenging sulfoxide tethers were the most effective in this transformation, showing a broad functionality tolerance, high S oxido-redox stability and no catalyst poisoning. Preliminary mechanistic studies indicate that the higher reactivity and selectivity shown by the sulfoxide tethers vs. the corresponding sulfones can be attributed to an extra coordination of the sulfoxide S atom to the catalyst. The utility of the presented methodology to generate structurally interesting aromatic derivatives by a subsequent modification of the S-tether is also exemplified.
- Richter, Heinrich,Beckendorf, Stephan,Mancheno, Olga Garcia
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supporting information; experimental part
p. 295 - 302
(2011/04/16)
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- Four new trace phenolic glycosides from Curculigo orchioides
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Four new trace phenolic glycosides named orcinosides D (1), E (2), F (3), and G (4) were isolated from the rhizomes of Curculigo orchioides Gaertn. Based on comprehensive spectroscopic analyses including IR, FAB-MS, HR-ESI-MS, 1D- and 2D NMR (HSQC, HMBC),
- Zuo, Ai-Xue,Shen, Yong,Zhang, Xue-Mei,Jiang, Zhi-Yong,Zhou, Jun,Lu, Jun,Chen, Ji-Jun
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experimental part
p. 43 - 50
(2010/09/04)
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- PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
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The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.
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- A new mild deprotecting method for O-benzylsulfonyl phenols and alcohols based on a DTBB-catalyzed lithiation
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A variety of alcohols and phenols, protected as the corresponding benzylsulfonic esters, were efficiently deprotected by selective reductive cleavage of the sulfur-oxygen bond, using an excess of lithium sand and a catalytic amount (5 mol%) of 4,4′-di-tert-butylbiphenyl (DTBB) as electron carrier, in THF at 0° C. This deprotection system was also efficient at -50 °C and was compatible with a wide range of other functional groups. Georg Thieme Verlag Stuttgart.
- Alonso, Francisco,Moglie, Yanina,Vitale, Cristian,Radivoy, Gabriel,Yus, Miguel
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p. 1971 - 1976
(2007/10/03)
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- Tyrosinase activity inhibitor
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Disclosed is a chemically stable tyrosinase activity inhibitor having high tyrosinase activity inhibition effect and low toxicity. The tyrosinase activity inhibitor has a structure of the formula: STR1 wherein R1, R3 and R4 are a hydrogen atom or an alkyl or alkenyl group having 1 to 9 carbon atoms, and R2 is an alkyl or alkenyl group having 2 to 9 carbon atoms.
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- Di-N-deacetyl-lysogangliosides
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The invention relates to N-deacetyl-lysogangliosides and physiologically acceptable salts thereof, especially those of formula (I): STR1 wherein R represents --CH=CH(CH2)nCH3 or --CH2 CH2 (CH2)nCH3 ; n is 12 or 14; R1 represents STR2 or hydrogen; and R2 represents hydrogen or acetyl; for use in therapy. The compounds are useful as inhibitors of phospholipases A2, and of superoxide production, as antiproliferative and immunosuppressant agents in the treatment of autoimmune diseases. The invention also relates to the use of N-deacetyl-lysogangliosides for the manufacture of medicaments for the treatment of the aforementioned conditions.
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- [3 + n] Annulation reactions by means of 3-trimethylstannyl-2-[(trimethylstannyl)methyl]propene, an isobutene dianion synthetic equivalent
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Stepwise functionalization of the two carbon-tin bonds in 3-trimethylstannyl)-2[(trimethylstannyl)methyl]propene with electrophiles (diacyl dichlorides or aldehydes and carbon dioxide, provides a promising route for [3 + n] annulation reactions.
- Degl'Innocenti,Dembech,Mordini,Ricci,Seconi
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p. 267 - 269
(2007/10/02)
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- Thermal Decomposition of Lichen Depsides
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The thermal decomposition of the following lichen depsides has been described: lecanoric acid, gyrophoric acid, evernic acid, perlatolic acid, planaic acid, confluentic acid, atranorin, 4-O-demethylbarbatic acid, and sekikaic acid.Main reaction products are decarboxylated compounds, phenolic units, rearranged depsides, and xanthones.Triethylammonium salts of depside carboxylic acids decompose at reasonably lower temperature than the corresponding free acids. - Keywords: Lichen Depsides, Thermal Decomposition
- Huneck, Siegfried,Schmidt, Juergen,Tabacchi, Raffaele
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p. 1283 - 1289
(2007/10/02)
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- Chemical Studies on the Lichen. I. The Structure of Isolecanoric Acid, a New ortho-Depside Isolated from Parmelia tinctorum Despr.
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A new ortho-depside, isolecanoric acid was isolated from Parmelia tinctorum Despr. and 2-(2,4-dihydroxy-6-methylbenzoyloxy)-4-hydroxy-6-methylbenzoic acid was assigned to this substance from studies on the hydrolysis products and from analyses of the 1H and 13C NMR spectra.This substance is the first ortho-depside isolated from the genus Lichen.
- Sakurai, Atsushi,Goto, Yohko
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p. 1917 - 1918
(2007/10/02)
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- Regiospecific Functionalization of the Monoterpene Ether 1,3,3-Trimethyl-2-oxabicyclooctane (1,8-Cineole). Synthesis of the Useful Bridged γ-Lactone 1,3-Dimethyl-2-oxabicyclooctan-3-->5-olide
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The regiospecific functionalization at C-5 and difuctionalization at C-5/C-8 and C-5/C-10 of the monoterpene 1,3,3-trimethyl-2-oxabicyclooctane (1) is described.Chromyl acetate oxidation of 1 afforded 1,3,3-trimethyl-2-oxabicyclooctan-5-one (6) in 60percent yield along with 28percent of unreacted 1 and minor amounts of exo-1,3,3-trimethyl-2-oxabicyclooctan-5-ol acetate (9), 1,3,3-trimethyl-2-oxabicyclooctane-5,8-dione (13), exo-8-acetoxy-1,3,3-trimethyl-2-oxabicyclooctan-5-one (16), 1,3,3-trimethyl-2-oxabicyclooctane-5,7-dione (14), and orcinol (15).On digestion with oxalic or phthalic acid, ketone 6 was converted into a mixture of piperitenone (20), 3-methyl-2-cyclohexenone (22), acetone, and traces of isopiperitenone (21), while 60percent sulfuric acid at room temperature yielded 20 as the sole reaction product.Oxidation of 6 with chromyl acetate yielded diketone 13, which decomposed into orcinol (15) on digestion with either boiling water or a 2.5percent sodium bicarbonate solution.Sodium borohydride or lithium aluminum hydride reduction of 6 gave stereospecifically exo-1,3,3-trimethyl-2-oxabicyclooctan-5-ol (7) while reduction with sodium-ethanol or aluminum isopropoxide in isopropyl alcohol (equilibrium conditions) yielded a 3:2 mixture of the alcohols 7 and 8, respectively.Treatment of 7 with phosphoryl chloride produced 1,3,3-trimethyl-2-oxatricyclo5,8>octane (25) together with minor amounts of the chlorocineoles 10 and 11.Pyrolysis of the methyl xanthate of 7 yielded 1,3,3-trimethyl-2-oxabicyclooct-5-ene (2).Photolysis of 7 in the presence of mercuric oxide and iodine or iodosylbenzene diacetate and iodine gave the tricyclic diether 29, which was quantitatively converted into the bridged γ-lactone 30 by oxidation with ruthenium tetraoxide.Oxidation of 29 with chromyl acetate yielded a 1:1 mixture of 30 and the formate lactone 31.Lithium aluminum hydride reduction of 30 produced diol 37, which was converted into menthofuran (44) in five steps.
- Boggiatto, Margarita V. de,Heluani, Carola S. de,Fenik, Ines J. S.,Catalan, Cesar A. N.
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p. 1505 - 1511
(2007/10/02)
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- Vat dye and sulfur dye compositions
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Specific vatting accelerators according to claims 1 and 2 are described. These can be added to a vat dye or sulfur dye composition, or to a dye bath or printing paste containing a vat dye or sulfur dye, by virtue of which an improvement of dye yield, particularly on cellulose materials, is obtained.
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- Improved Synthesis of Dichloroisoeverninic Acid
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The Dichlorination of methyl isoeverninate 7a gave the geminal dichloroketone 12 as the major product.The title compound 1 was therefore synthesized via dichlorination of 4-protected methyl orsellinate 5a using the pivaloyloxy-function as a new protecting group in resorcyclic acids chemistry. - Keywords: 3,5-Dichloro-4-hydroxy-2-methoxy-6-methylbenzoic Acid, Dichloroisoeverninic Acid
- Dornhagen, Juergen,Scharf, Hans-Dieter
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p. 1541 - 1549
(2007/10/02)
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- Fungus Pigments, 40. Leprocybin, the Fluorescent Principle of Cortinarius cotoneus and related Leprocybes (Agaricales)
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Leprocybin (1), a glucoside responsible for the yellow-green fluorescence of the fruiting bodies under UV light has been isolated from Cortinarius toadstools (subgenus Leprocybe, section Leprocybe Mos.).On acid hydrolysis or action of β-glucosidase 1 was split into its aglycone leprocyboside (6), the constitution of which was elucidated by several derivatisations, decarboxylation to 10, and alkaline degradation.Final structural proof of the pyranoxanthone system was obtained by synthesis of 8-O-methyl(decarboxy)leprocyboside (12).
- Kopanski, Lothar,Klaar, Manfred,Steglich, Wolfgang
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p. 1280 - 1296
(2007/10/02)
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- REACTION OF PHENOLS AND THEIR DERIVATIVES WITH AROMATIC COMPOUNDS IN THE PRESENCE OF ACIDIC AGENTS IV. CONDENSATION OF SUBSTITUTED RESORCINOLS WITH BENZENE AND CHLOROBENZENE
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In the presence of aluminium chloride 5-methyl-, 5-phenyl, and 5- and 4-chlororesorcinols are brought into condensation with benzene through positions 5 or 3, depending on the nature of substituent.
- Repinskaya, I. B.,Koptyug, V. A.
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p. 1298 - 1303
(2007/10/02)
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- Course of Aromatisation of 5-Alkyl/aryl-2-bromocyclohex-2-en-3-ol-1-ones to Corresponding 5-Alkyl/arylresorcinols
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5-Alkyl/aryl-2-bromocyclohex-2-en-3-ol-1-ones on heating undergo aromatisation through dehydrobromination to the corresponding 5-substituted resorcinols.During the course of aromatisation of 2-bromo-5-methylcyclohex-2-en-3-ol-1-one (I) and 5-n-amyl-2-bromocyclohex-2-en-3-ol-1-one (II) a few intermediates have been isolated and characterised as IV, V, VI, VIII and IX.Similar studies on 2-bromo-5-phenylcyclohex-2-en-3-ol-1-one yields two structurally different products, one with no bromine (XI) and the other with bromine in position-2 (XII), besides 5-phenylresorcinol (XIII).
- Chandrasekharan, V.,Unnikrishnan, P.,Shah, G. D.,Bhattacharyya, S. C.
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p. 1052 - 1055
(2007/10/02)
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- BORON TETRAHALIDE-METHYL SULFIDE COMPLEXES AS CONVENIENT REAGENTS FOR DEALKYLATION OF ARYL ETHERS
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High yield dealkylation of several aryl methyl ethers was observed upon exposure of these compounds to an excess of the boron trihalidemethyl sulfide complexes.
- Williard, Paul G.,Fryhle, Craig B.
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p. 3731 - 3734
(2007/10/02)
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- A New Route to 5-Substituted Resorcinols and Related Systems
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Michael-type additions of phenylsulphinylacetate esters to αβ-unsaturated ketones produce cyclohexane-1,3-dione derivatives, which, after thermal elimination of benzenesulphenic acid, give the corresponding 5-substituted resorcinols, such as olivetol.The scope of this entry into other aromatic systems, such as 3,5-disubstituted and 2,3,5-trisubstituted phenols and orsellinic acid has been explored.
- Jaxa-Chamiec, Albert A.,Sammes, Peter G.,Kennewell, Peter D.
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p. 170 - 175
(2007/10/02)
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- Process for the preparation of 5-substituted resorcinols and related intermediates
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According to the present invention, 5-substituted resorcinols of the formula I STR1 wherein R1 represents a hydrocarbon radical, optionally unsubstituted or substituted by inert substituents, are prepared by reacting a carboxylic acid ester of the formula II wherein R2 represents a non-aromatically bound lower hydrocarbon radical, in the presence of an alkaline condensation agent, with a diester of 3-oxoglutaric acid of the formula III wherein R3 and R4 represent non-aromatically bound lower hydrocarbon radicals; hydrolyzing the resulting dihydroxyisophthalic acid acid ester of the formula IV STR2 and decarboxylating the hydrolyzed product, a specific embodiment is the preparation of 5-pentylresorcinol.
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