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Journal articles on the topic 'Hydroxy groups'

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Published: 5 June 2025

Last updated: 24 June 2025

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1

S., GOPALAKRISHNAN, NEELAKANIAN S., and V. RAMAN P. "Visible Absorption Spectra of Anthraquinones : Use of Shift Reagents in Structure Determination." Journal of Indian Chemical Society Vol. 67, May 1990 (1990): 390–93. https://doi.org/10.5281/zenodo.6163405.

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Department of Chemistry, Madurai Kamaraj University Post-Graduate Extension Centre, Palayamkottai-627 002 Department of Natural Products Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai-625 021 <em>Manuscript received 13 July 1989, accepted 21 November 1989</em> A careful analysis of the bathochromic shifts induced by the usual shift reagents on the 'last visible band' (LVB) of the visible absorption spectra of twentysix hydroxyanthraquinones has revealed the usefulness of these shift reagents in the allocation of the hydroxyl groups in these compounds. Empirical rules very similar to those developed with flavonoids are advanced and their utility as well as limitations discussed.

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2

Ivashkiv, Ostap, Jacek Namiesnik, Olena Shyshchak, Igor Polyuzhyn, and Michael Bratychak. "Synthesis and Properties of Oligomers with Hydroxy End-Groups." Chemistry & Chemical Technology 10, no. 4s (2016): 587–94. http://dx.doi.org/10.23939/chcht10.04si.587.

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Methods of oligomers (polymers) with hydroxy end-groups obtaining are examined. The synthesis of hydroxy-containing oligomers based on epoxy resins is of special attention. The molecules of mentioned oligomers apart from free primary and secondary hydroxy groups contain epoxy, peroxy, carboxy or acrylic groups.

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3

Sousa, Andreia F., Alessandro Gandini, Armando J. D. Silvestre, and Carlos Pascoal Neto. "Determination of the Hydroxy and Carboxylic Acid Groups in Natural Complex Mixtures of Hydroxy Fatty Acids by 1H Nuclear Magnetic Resonance Spectroscopy." Applied Spectroscopy 63, no. 8 (2009): 873–78. http://dx.doi.org/10.1366/000370209788964557.

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The use of trichloroacetyl isocyanate (TAI) to mark both hydroxyl and carboxyl groups borne by the hydrolysis or methanolysis of suberin fragments (a complex mixture of hydroxy fatty acids), allowed the quantitative assessment of the ratio between carboxyl and hydroxy groups, as well as the ratio between primary and secondary hydroxy groups, to be carried out reliably by 1H nuclear magnetic resonance (NMR) spectroscopy. All the samples thus analyzed displayed an excess of CO2H (or CO2CH3) functions with respect to the OH counterparts, albeit to a variable extent, depending on the procedure adopted to isolate the suberin fragments. The precise knowledge of the molar ratio of these two reactive moieties is fundamental for the correct utilization of suberin monomers in polymerization reactions leading to aliphatic polyesters.

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4

Russell, V. A., and M. D. Ward. "Solid-state structure of a layered hydrogen-bonded salt: guanidinium 5-benzoyl-4-hydroxy-2-methoxybenzenesulfonate methanol solvate." Acta Crystallographica Section B Structural Science 52, no. 1 (1996): 209–14. http://dx.doi.org/10.1107/s0108768195009980.

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Guanidinium 5-benzoyl-4-hydroxy-2-methoxybenzene-sulfonate methanol solvate [C(NH2)3 +.(C14H11O3)SO3 −.CH3OH] crystallizes into a layered structure containing a two-dimensional hydrogen-bonded network typical of guanidinium alkane- and arenesulfonates. All six guanidinium protons and six sulfonate oxygen lone-pair acceptors participate in hydrogen bonding to form nearly planar pseudohexagonal hydrogen-bonded sheets, which can be viewed as parallel connected hydrogen-bonded ribbons. The 5-benzoyl-4-hydroxy-2-methoxybenzene groups are oriented to the same side of each ribbon, but the orientation of these groups on adjacent ribbons alternates with respect to the hydrogen-bonded sheet. The planar sheets stack with interdigitation of the arene groups, resulting in a structure in which layers of 5-benzoyl-4-hydroxy-2-methoxybenzene groups are separated by ionic hydrogen-bonded sheets. Each methanol molecule forms a hydrogen bond to one of the sulfonate O atoms, resulting in this oxygen forming a total of three hydrogen bonds, and fills void volume between the interdigitated 5-benzoyl-4-hydroxy-2-methoxybenzene groups of neighboring sheets. The benzophenone hydroxyl proton forms an intramolecular hydrogen bond to the carbonyl oxygen.

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5

Stanchev, Stancho, Cäcilia Maichle-Mössmer, and Ilia Manolov. "Synthesis, Structure and Acid-Base Behaviour of Some 4-Hydroxycoumarin Derivatives." Zeitschrift für Naturforschung B 62, no. 5 (2007): 737–41. http://dx.doi.org/10.1515/znb-2007-0519.

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Abstract The compound 3,3′-[(4-hydroxy-3-methoxy-5-nitrophenyl)methylene]-bis(4-hydroxy-2H-1- benzopyran-2-one) (1) crystallizes in the monoclinic system, space group P21/n, with cell constants a = 16.859(4), b = 6.1624(15), c = 25.164(4) Å , β = 98.019(19)°. The two 4-hydroxycoumarin fragments are intramolecularly hydrogen-bonded between hydroxyl and carbonyl groups. The pH-dependent color changes of 4-hydroxycoumarin derivatives were studied by means of potentiometric and spectrophotometric titration. On the basis of the results obtained, the use of 3,3′-[(4-hydroxy-3- methoxy-5-nitrophenyl)methylene]-bis(4-hydroxy-2H-1-benzopyran-2-one) as an indicator in alkalimetry and acidimetry is proposed.

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6

Xu, Xing-You, Tong-Tao Xu, Shuai-Shuai Ni, Jian Gao, and Da-Qi Wang. "Bis{2-[1-(benzylimino)ethyl]-5-methoxyphenol}dichlorozinc(II)." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (2006): m1548—m1549. http://dx.doi.org/10.1107/s1600536806021829.

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The title complex, [ZnCl2(C16H17NO2)2], displays a distorted tetrahedral coordination geometry around the ZnII ion. The Schiff base inner salt, (benzylimino)ethyl-5-methoxyphenol, coordinates in a monodentate manner to the ZnII ion via the deprotonated hydroxy groups. The protonated imino groups form intramolecular hydrogen bonds with the deprotonated hydroxyl groups of the same Schiff base ligand.

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7

Kozmík, Václav, та Jaroslav Paleček. "Synthetic Analogues of Prostaglandins F2α and E2". Collection of Czechoslovak Chemical Communications 59, № 1 (1994): 138–48. http://dx.doi.org/10.1135/cccc19940138.

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The synthesis of new derivatives of prostaglandins F2α and E2 XIIa,b - XVa,b and XXa,b - XXIIIa,b containing the furan or thiophene nucleus in the upper chain has been accomplished starting from [3aα,4α,5β,6aα]-(±)-hexahydro-5-hydroxy-4-((E)-(3α)-hydroxy-1-octenyl)-2H-cyclopenta[b]furan-2-one (Ia) and [3aα,4α,5β,6aα]-(±)-hexahydro-5-hydroxy-4-[4-(3-chlorophenoxy)-(3α)-hydroxy-1-butenyl]cyclopenta[b]furan-2-one (Ib). The diols Ia and Ib have been converted into the above-mentioned analogues of prostaglandins F2α and E2 by protecting the hydroxyl groups, subsequent reduction and Wittig reaction with the ylides prepared from the phosphonium salts IV - VII, and final deprotection (or oxidation plus deprotection).

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8

Kasal, Alexander, та Jaroslav Zajíček. "Spontaneous transannular reaction in Δ9-unsaturated A-homo-B,19-dinorsteroids". Collection of Czechoslovak Chemical Communications 54, № 5 (1989): 1327–35. http://dx.doi.org/10.1135/cccc19891327.

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The epoxidation of 3β-hydroxy derivatives of Δ9-unsaturated A-homo-B,19-dinorsteroids (type I-IV) proceeds with spontaneous participation of the 3β-hydroxyl under formation of transannular 9α-hydroxy-3β,10β-oxides IX, X, XV and XVII. Epoxidation of the corresponding esters V-VIII affords predominantly 9α,10α-epoxides XIV, XVI, XVIII and XIX which, after hydrolysis of the ester groups are also converted into the transannular 3β,10β-oxides of the type IX.

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9

Doden, Heidi L., and Jason M. Ridlon. "Microbial Hydroxysteroid Dehydrogenases: From Alpha to Omega." Microorganisms 9, no. 3 (2021): 469. http://dx.doi.org/10.3390/microorganisms9030469.

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Bile acids (BAs) and glucocorticoids are steroid hormones derived from cholesterol that are important signaling molecules in humans and other vertebrates. Hydroxysteroid dehydrogenases (HSDHs) are encoded both by the host and by their resident gut microbiota, and they reversibly convert steroid hydroxyl groups to keto groups. Pairs of HSDHs can reversibly epimerize steroids from α-hydroxy conformations to β-hydroxy, or β-hydroxy to ω-hydroxy in the case of ω-muricholic acid. These reactions often result in products with drastically different physicochemical properties than their precursors, which can result in steroids being activators or inhibitors of host receptors, can affect solubility in fecal water, and can modulate toxicity. Microbial HSDHs modulate sterols associated with diseases such as colorectal cancer, liver cancer, prostate cancer, and polycystic ovary syndrome. Although the role of microbial HSDHs is not yet fully elucidated, they may have therapeutic potential as steroid pool modulators or druggable targets in the future. In this review, we explore metabolism of BAs and glucocorticoids with a focus on biotransformation by microbial HSDHs.

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10

Hu, Thomas Q., Graham R. Cairns, and Brian R. James. "Removal of Phenolic Hydroxyl Groups in Lignin Model Compounds and Its Effect on Photostability." Holzforschung 54, no. 2 (2000): 127–32. http://dx.doi.org/10.1515/hf.2000.022.

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Summary The phenolic hydroxyl groups in the lignin model compounds, 2-methoxy-4-propylphenol and 4-hydroxy-3-methoxyacetophenone, were removed by first converting the hydroxyl groups to the trifluoromethanesulfonates (triflates) and then cleaving the triflate substituents via catalytic hydrogen transfer. The products, 1-methoxy-3-propylbenzene and 3-methoxyacetophenone, were characterized by 1H and 13C NMR, mass spectrometry and elemental analyses. The effect of the removal of the phenolic groups on the photostability of the model compounds was evaluated by impregnating the compounds into Whatman filter paper sheets, and subjecting them to an accelerated yellowing experiment in a UV chamber. The removal of the phenolic groups resulted in a significant yellowing inhibition, with a higher photostabilizing effect than methylation or acetylation of the hydroxyl, particularly for the model compound without an α-carbonyl group.

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11

Salas-Reyes, V. "Chiral Synthesis of (R)-(-)(5Z)-4-Hydroxy-5-tetradecenoic Acid-4-lactone." Zeitschrift für Naturforschung B 50, no. 10 (1995): 1537–42. http://dx.doi.org/10.1515/znb-1995-1018.

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R -(-)(5Z)-4-hydroxy-5-tetradecenoic acid-4-lactone has been synthesized from D-glucose as the precursor. Regio and stereoselective transformations of hydroxyl groups as well as protection-deprotection protocols provide a novel route to this compound.

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12

Lyu, Baohe, Yoshikazu Hiraga, Ryukichi Takagi, and Satomi Niwayama. "Complete Assignments of 1H and 13C NMR Chemical Shift Changes Observed upon Protection of Hydroxy Group in Borneol and Isoborneol and Their DFT Verification." Molecules 30, no. 3 (2025): 597. https://doi.org/10.3390/molecules30030597.

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Complete assignments of the 1H and 13C NMR chemical shifts for the monoterpenes, borneol 1a and isoborneol 2a, as well as their derivatives (1b–1g and 2b–2g), in which the secondary hydroxy group is protected with various protecting groups, have been made in various solvents. Upon protection of the hydroxy groups in 1a and 2a, many protons and carbons within the bicyclic ring exhibited downfield or upfield shifts in their chemical shift values, facilitating the unambiguous assignments of these protons and carbons. These chemical shift values also showed excellent correlations with those obtained from density functional theory (DFT) calculations. Furthermore, the anisotropic effect of the benzene ring was estimated by the analysis of the iso-chemical shielding surface (ICSS) resulting from substituents introduced to the hydroxyl groups of 1a and 2a.

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13

Pouzar, Vladimír, Lenka Schneiderová, Pavel Drašar, Oldřich Štrouf, and Miroslav Havel. "Synthesis of 2-propynyl ethers of steroid alcohols." Collection of Czechoslovak Chemical Communications 54, no. 7 (1989): 1888–902. http://dx.doi.org/10.1135/cccc19891888.

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2-propynyl ethers, derived from steroid alcohols with hydroxyl in position 3β, 17 or 20, were prepared by reaction with propargyl bromide and sodium hydroxide under conditions of phase transfer catalysis. Other hydroxy groups in the steroid molecule were protected with the methoxymethyl or 2-tetrahydropyranyl group.

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14

Gomes, Ligia R., Marcus V. N. de Souza, Cristiane F. Da Costa, James L. Wardell, and John Nicolson Low. "Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X = Me, OH and MeO)." Acta Crystallographica Section E Crystallographic Communications 74, no. 10 (2018): 1480–85. http://dx.doi.org/10.1107/s2056989018013361.

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The crystal structures of three salicyaldoxime compounds, namely 2-hydroxy-4-methylbenzaldehyde oxime, C8H9NO2, 1, 2,4-dihydroxybenzaldehyde oxime, C7H7NO3, 2, and 2-hydroxy-4-methoxybenzaldehyde oxime, C8H9NO3, 3, are discussed. In each compound, the hydroxyl groups are essentially coplanar with their attached phenyl group. The interplanar angles between the C=N—O moieties of the oxime unit and their attached phenyl rings are 0.08 (9), 1.08 (15) and 6.65 (15)° in 1, 2 and 3, respectively. In all three molecules, the 2-hydroxy group forms an intramolecular O—H...N(oxime) hydrogen bond. In compound (1), intermolecular O—H(oxime)...O(hydroxyl) hydrogen bonds generate R 2 2(14) dimers, related by inversion centres. In compound 2, intermolecular O—H(oxime)...O(4-hydroxy) hydrogen bonds generate C9 chains along the b-axis direction, while O—H(4-hydroxyl)...O(2-hydroxyl) interactions form zigzag C6 spiral chains along the c-axis direction, generated by a screw axis at 1, y, 1/4: the combination of the two chains provides a bimolecular sheet running parallel to the b axis, which lies between 0–1/2 c and 1/2–1 c. In compound 3, similar C9 chains, along the b-axis direction are generated by O—H(oxime)...O(4-methoxy) hydrogen bonds. Further weaker, C—H...π (in 1), π–π (in 2) and both C—H...π and π–π interactions (in 3) further cement the three-dimensional structures. Hirshfeld surface and fingerprint analyses are discussed.

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15

Noguchi, Masato. "Regioselective Protection of Hydroxy Groups in Sugars." Trends in Glycoscience and Glycotechnology 26, no. 151 (2014): 145–47. http://dx.doi.org/10.4052/tigg.26.145.

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16

de Leeuw, N. H. "Local ordering of hydroxy groups in hydroxyapatite." Chemical Communications, no. 17 (2001): 1646–47. http://dx.doi.org/10.1039/b104850n.

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17

Jentys, Andreas, Ngan H. Pham, and Hannelore Vinek. "Nature of hydroxy groups in MCM-41." Journal of the Chemical Society, Faraday Transactions 92, no. 17 (1996): 3287. http://dx.doi.org/10.1039/ft9969203287.

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18

Montero, Jean-Louis, Catherine Toiron, Jean-Louis Clavel, and Jean-Louis Imbach. "Phosphorylation of hydroxy groups via silylated intermediates." Recueil des Travaux Chimiques des Pays-Bas 107, no. 9 (2010): 570–72. http://dx.doi.org/10.1002/recl.19881070909.

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19

Rani, Reshma, and Carlotta Granchi. "Bioactive heterocycles containing endocyclic N-hydroxy groups." European Journal of Medicinal Chemistry 97 (June 2015): 505–24. http://dx.doi.org/10.1016/j.ejmech.2014.11.031.

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20

Ivashkiv, Ostap, Piotr Bruzdziak, Olena Shyshchak, Jacek Namiesnik, and Michael Bratychak. "Determination of Hydroxy Groups in the Modified Epoxy Oligomers Using IR-Spectroscopy." Chemistry & Chemical Technology 9, no. 4 (2015): 411–16. http://dx.doi.org/10.23939/chcht09.04.411.

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21

Beč, Anja, Katarina Zlatić, Mihailo Banjanac, et al. "Design, Synthesis and Biological Activity of Novel Methoxy- and Hydroxy-Substituted N-Benzimidazole-Derived Carboxamides." Molecules 29, no. 9 (2024): 2138. http://dx.doi.org/10.3390/molecules29092138.

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This work presents the design, synthesis and biological activity of novel N-substituted benzimidazole carboxamides bearing either a variable number of methoxy and/or hydroxy groups. The targeted carboxamides were designed to investigate the influence of the number of methoxy and/or hydroxy groups, the type of substituent placed on the N atom of the benzimidazole core and the type of substituent placed on the benzimidazole core on biological activity. The most promising derivatives with pronounced antiproliferative activity proved to be N-methyl-substituted derivatives with hydroxyl and methoxy groups at the phenyl ring and cyano groups on the benzimidazole nuclei with selective activity against the MCF-7 cell line (IC50 = 3.1 μM). In addition, the cyano-substituted derivatives 10 and 11 showed strong antiproliferative activity against the tested cells (IC50 = 1.2–5.3 μM). Several tested compounds showed significantly improved antioxidative activity in all three methods compared to standard BHT. In addition, the antioxidative activity of 9, 10, 32 and 36 in the cells generally confirmed their antioxidant ability demonstrated in vitro. However, their antiproliferative activity was not related to their ability to inhibit oxidative stress nor to their ability to induce it. Compound 8 with two hydroxy and one methoxy group on the phenyl ring showed the strongest antibacterial activity against the Gram-positive strain E. faecalis (MIC = 8 μM).

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22

Ismayilova, G. G. "Synthesis and research of xanthogenic acid derivatives with different polar groups as additives to transmission oils." World of petroleum products 5-6 (2022): 12–15. http://dx.doi.org/10.32758/2782-3040-2022-0-5-12-15.

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Derivatives of xanthogenic acids containing amine and hydroxyl groups were synthesized on the basis of epichlorohydrin. The three-component reaction of epichlorohydrin with various potassium alkylxanthogenates and a secondary amine, whereby the secondary amine was taken strictly according to the calculations, was to obtain β-hydroxy-γ-dibutylaminopropyl esters of alkylxanthogenic acids. The structure of β-hydroxy-γ-dibutylaminopropyl esters of alkylxanthogenic acids was confirmed by IR spectroscopy. Alkylxanthogenic acid derivatives have been investigated as additives for transmission oils. All derivatives had effective tribological characteristics, that is, extreme pressure and antiwear properties.An increase in the alkyl radical leads to some change in extreme pressure properties, reducing the scuffing index from 570N to 530N and the critical load from 1260N to 1190 N. The connections were tested in SN-1200 base oil and I-40A industrial oil. In both oils, they showed better efficiency than additives LZ-23k and ABES, especially in terms of antiwear properties. The study of the effect of the test duration on the antiwear properties revealed their better response over a long period of time  6 and 8 hours than the ABES additive.

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23

Kostopoulou, Ioanna, Andromachi Tzani, Nestor-Ioannis Polyzos, et al. "Exploring the 2′-Hydroxy-Chalcone Framework for the Development of Dual Antioxidant and Soybean Lipoxygenase Inhibitory Agents." Molecules 26, no. 9 (2021): 2777. http://dx.doi.org/10.3390/molecules26092777.

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2′-hydroxy-chalcones are naturally occurring compounds with a wide array of bioactivity. In an effort to delineate the structural features that favor antioxidant and lipoxygenase (LOX) inhibitory activity, the design, synthesis, and bioactivity profile of a series of 2′-hydroxy-chalcones bearing diverse substituents on rings A and B, are presented. Among all the synthesized derivatives, chalcone 4b, bearing two hydroxyl substituents on ring B, was found to possess the best combined activity (82.4% DPPH radical scavenging ability, 82.3% inhibition of lipid peroxidation, and satisfactory LOX inhibition value (IC50 = 70 μM). Chalcone 3c, possessing a methoxymethylene substituent on ring A, and three methoxy groups on ring B, exhibited the most promising LOX inhibitory activity (IC50 = 45 μM). A combination of in silico techniques were utilized in an effort to explore the crucial binding characteristics of the most active compound 3c and its analogue 3b, to LOX. A common H-bond interaction pattern, orienting the hydroxyl and carbonyl groups of the aromatic ring A towards Asp768 and Asn128, respectively, was observed. Regarding the analogue 3c, the bulky (-OMOM) group does not seem to participate in a direct binding, but it induces an orientation capable to form H-bonds between the methoxy groups of the aromatic ring B with Trp130 and Gly247.

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24

Charlton, James L., Guy L. Plourde, Kevin Koh та Anthony S. Secco. "Diels–Alder addition of the fumarate and acrylate of S-methyl lactate to α-hydroxy orthoquinodimethanes". Canadian Journal of Chemistry 67, № 4 (1989): 574–79. http://dx.doi.org/10.1139/v89-087.

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The cycloaddition of α-hydroxy orthoquinodimethane, generated photochemically from 2-methylbenzaldehyde, to the fumarate and acrylate of S-methyl lactate has been found to give a single diastereomer with high asymmetric induction (>95% de). This reaction provides a new and versatile synthetic route to substituted tetralins of high optical purity. A trans stereochemistry between the vicinal hydroxyl and carboxylactyl groups has been established for these cycloadducts. This is in contrast to previous work where cis stereochemistry has always been found for major cycloadducts of α-hydroxy o-QDMs. The high asymmetric induction, unusual diastereoselectivity, and the potential use of these reactions in asymmetric synthesis are discussed. Keywords: o-quinodimethanes, Diels–Alder, asymmetric, cycloaddition, induction, diastereoselective.

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25

Qiao, Liqin, Yao Dong, Hongli Zhou, and Hao Cui. "Effect of Post–Polyketide Synthase Modification Groups on Property and Activity of Polyene Macrolides." Antibiotics 12, no. 1 (2023): 119. http://dx.doi.org/10.3390/antibiotics12010119.

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The biosynthesis of polyene macrolides, which are natural products produced by soil actinomycetes, have been extensively explored, and recent studies have focused on the effects of post–polyketide synthase (PKS) modifications to polyene macrolides on toxicity, water solubility, and antifungal activity. For example, there are interactions between glycosyl, carboxyl, and hydroxyl or epoxy groups generated in the post-PKS modification steps; salt bridges will be formed between carboxylate and ammonium on the mycosamine; and water bridges will be formed between hydroxy and hydroxyl on mycosamine. These interactions will affect their water solubility and substrate-recognition specificity. This review summarizes research related to these post-PKS modification groups and discusses some genetic engineering operation problems and solutions that may be encountered when modifying these post-PKS modification groups. In addition, this review provides a basis for the structural research of polyene macrolide antibiotics and contributes to comprehensive and systematic knowledge, and it may thus encourage researchers to develop novel antifungal drugs with higher therapeutic indexes and medical values.

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26

Liang, Zehong, Henna Koivikko, Mikko Oivanen, and Petri Heinonen. "Tuning the stability of alkoxyisopropyl protection groups." Beilstein Journal of Organic Chemistry 15 (March 21, 2019): 746–51. http://dx.doi.org/10.3762/bjoc.15.70.

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Five different 2-alkoxypropan-2-yl groups are introduced as acid-labile protecting groups for the 5’- and 3’-hydroxy groups of a 2’-deoxynucleoside. All studied protecting groups were readily introduced with good to excellent yields using the appropriate enol ether as a reagent and 0.5 to 1 mol % p-toluenesulfonic acid as a catalyst. The protected compounds could be purified by silica gel column chromatography without degradation. The compatibility of these protecting groups in parallel use with benzoyl and silyl groups was verified. The stabilities of the different alkoxy acetal protecting groups were compared by following the kinetics of their hydrolysis at 25.0 °C in buffered solutions through an HPLC method. In the pH range 4.94 to 6.82 the hydrolysis reactions are of first order in the hydronium ion. The rate of hydrolysis correlates with the electron-donating or electron-withdrawing ability of the corresponding alkoxy group. The studied 2-alkoxypropan-2-yl groups and the relative rate constants for their cleavage from the 5’-hydroxy group of 2’-deoxythymidine were: cyclohexyloxy (k rel = 7.7), isopropoxy (7.4), methoxy (1), benzyloxy (0.6) and 2,2,2-trifluoroethyloxy (0.04). The attachment of the same groups to the 3’-hydroxy group are from 1.3 to 1.9-fold more stable. The most reactive of these acetone-based acetal groups are faster removed than a dimethoxytrityl group, and they are easier to cleave completely in solution. The structural variation allows steering of the stability and lipophilicity of the compounds in some range.

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27

Traven, Valery F., Vadim V. Negrebetsky, Larisa I. Vorobjeva, and Edward Andrew Carberry. "Keto–enol tautomerism, NMR spectra, and H–D exchange of 4-hydroxycoumarins." Canadian Journal of Chemistry 75, no. 4 (1997): 377–83. http://dx.doi.org/10.1139/v97-043.

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4-Hydroxycoumarin 1, 4,5-dihydroxycoumarin 2, and 4,7-dihydroxycoumarin 3 undergo H–D exchange at the C(3) atom of the lactone ring. Although only the 4-hydroxy-2-chromenone tautomeric forms are seen in the 1H and 13C NMR spectra of compounds 1–3, the equilibrium between the 4-hydroxy-2-chromenone and 2,4-chromandione forms is suggested to be the key step in the H–D exchange reaction. 4,5-Dihydroxycoumarin shows the highest rate of the reaction, since H-bonding between 5-hydroxyl and 4-keto functional groups can provide relative stability to the 5-hydroxy-2,4-chromandione tautomeric form, a probable intermediate of the exchange. NMR spectra and tautomeric transformations of 3-(4-methoxyphenylazo)-4-hydroxycoumarin 4 and 3-acetyl-4-hydroxycoumarin 5 are also discussed. The stabilities of different tautomeric forms of compounds 1–5 have been evaluated by MNDO calculations. Keywords: 4-hydroxycoumarin derivatives, keto-enol tautomerism, H–D-exchange.

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28

Datka, J., and T. Abramowicz. "Hydroxy groups in ferrisilicates studied by IR spectroscopy." Journal of the Chemical Society, Faraday Transactions 90, no. 16 (1994): 2417. http://dx.doi.org/10.1039/ft9949002417.

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29

Kim, Chungkyun, Sungmo Son, and Bohyun Kim. "Dendritic carbosilanes containing hydroxy groups on the periphery." Journal of Organometallic Chemistry 588, no. 1 (1999): 1–8. http://dx.doi.org/10.1016/s0022-328x(99)00335-6.

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30

Fejes, P., I. Hannus, I. Kiricsi, H. Pfeifer, D. Freude, and W. Oehme. "Thermal stability of hydroxy groups in dealuminated mordenites." Zeolites 5, no. 1 (1985): 45–48. http://dx.doi.org/10.1016/0144-2449(85)90011-9.

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31

Gatti, Pier Andrea, Stefania Gagliardi, Alberto Cerri, Marco Visconti, and Carlo Farina. "Selective Oxidation of Hydroxy Groups of Bafilomycin A1." Journal of Organic Chemistry 61, no. 20 (1996): 7185–88. http://dx.doi.org/10.1021/jo9607222.

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32

Sahade, Daniel A., Shuntaro Mataka, Tsuyoshi Sawada, Takehito Tsukinoki, and Masashi Tashiro. "[2.2]Metacyclophanes having hydroxy groups on the bridge." Tetrahedron Letters 38, no. 21 (1997): 3745–46. http://dx.doi.org/10.1016/s0040-4039(97)00743-0.

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33

Shadid, B. R., H. C. van der Plas, E. de Vroom, G. A. van der Marel, and J. H. van Boom. "Phosphorylation of allylic hydroxy groups via phosphite intermediates." Recueil des Travaux Chimiques des Pays-Bas 106, no. 9 (2010): 509–11. http://dx.doi.org/10.1002/recl.19871060907.

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34

Rubtsova, Daria D., Alexandra A. Bobyleva, Daria D. Lezhnina, Sofia V. Polikarpova, Polina A. Rozhkova, and Vladimir L. Gein. "Synthesis of 5-aryl-3-hydroxy-1-(2-hydroxypropyl)-4-(furyl-2-carbonyl)- 3-pyrrolin-2-ones and 5-aryl-3-hydroxy-1-(3-hydroxypropyl)- 4-(furyl-2-carbonyl)-3-pyrrolin-2-ones." Butlerov Communications 63, no. 9 (2020): 26–30. http://dx.doi.org/10.37952/roi-jbc-01/20-63-9-26.

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In this work, pyrrolidin-2-ones and their derivatives are considered as a promising class of non-aromatic heterocyclic compounds. Their structure is found in the nuclei of many natural products and biologically active molecules. In pharmacy the possibility of introducing various substituents into the nucleus of pyrrolidin-2-ones is a great importance for the synthesis of new medicinal molecules with improved biological activity. Nowadays the synthesis of new active compounds by introducing various substituents at the C1-, C4- and C5-position of 3-hydroxy-3-pyrrolin-2-one has been little studied and it is of great interest to study the conditions of their synthesis, chemical properties and biological activity. In this research work the corresponding 5-aryl-3-hydroxy-1-(2-hydroxypropyl)-4-(furyl-2-carbonyl)-3-pyrrolin-2-ones and 5-aryl-3-hydroxy-1-(3-hydroxypropyl)-4-(furyl-2-carbonyl)-3-pyrrolin-2-ones were synthesized by the reaction of methyl ester of furyl-2-carbonylpyruvic acid with a mixture of aromatic aldehyde and 1-amino-2-hydroxypropane or 3-amino 1-hydroxypropane when heated in dioxane. The results of the study of the structure of the new synthesized compounds are presented. The structure was proved using 1H NMR spectroscopy and IR spectrometry. It was shown that the IR spectra of the compounds contain bands of the corresponding stretching vibrations of the alcoholic hydroxyl group, enol hydroxyl, amide and ketone groups. In the 1H NMR spectra of the compounds, along with the signals of aromatic protons in the C5 substituent and related groups, characteristic peaks are observed, indicating the formation of the corresponding derivatives of 3-hydroxy-3-pyrrolin-2-ones. It was noted that in the case of the synthesis of 5-aryl-3-hydroxy-1-(2-hydroxypropyl)-4-(furyl-2-carbonyl)-3-pyrrolin-2-ones, the signal of the methine proton at the C5 position of the heterocycle is cleaved in 1H NMR spectra compounds as a result of the appearance of a second chiral center in the 2-hydroxypropyl radical. Elemental analysis was performed for the synthesized compounds.

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35

Velisek, Josef, Alzbeta Stara, Dalibor Koutnik, and Jana Machova. "Effect of Terbuthylazine-2-hydroxy at Environmental Concentrations on Early Life Stages of Common Carp (Cyprinus carpioL.)." BioMed Research International 2014 (2014): 1–7. http://dx.doi.org/10.1155/2014/621304.

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The aim of the study was to investigate effects of the triazine’s herbicide terbuthylazine-2-hydroxy on early life stage of common carp (Cyprinus carpioL.) through antioxidant indices, mortality, growth, development, and histopathology. Based on accumulated mortality in the experimental groups, lethal concentrations of terbuthylazine-2-hydroxy were estimated at 35-day LC50 = 10.9 mg/L terbuthylazine-2-hydroxy. By day 15, fish were exposed to 3.5 mg/L and by day 26, fish were exposed to 0.0029 mg/L; real environmental concentration in Czech rivers, 0.07 mg/L, 1.4 mg/L, and 3.5 mg/L terbuthylazine-2-hydroxy, showed significantly lower mass and total length compared with controls. Based on inhibition of growth in the experimental groups, lowest observed effect concentration (LOEC) = 0.002 mg/L terbuthylazine-2-hydroxy and no observed effect concentration (NOEC) = 0.0001 mg/L terbuthylazine-2-hydroxy. No significant negative effects on hatching or embryo viability were demonstrated at the concentrations tested, but significant differences in early ontogeny among groups were noted. Fish from the two highest tested concentrations showed a dose-related delay in development compared with the controls. Total superoxide dismutase (SOD) activity was significant lower in all groups testedly for terbuthylazine-2-hydroxy compared with the control group. At concentrations of 1.4 and 3.5 mg/L damage to caudal kidney tubules when compared to control fish was found.

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36

Trudell, Mark, Ryan McKinnie, Tasneam Darweesh, Phoebe Zito, and Terrell Shields. "Synthesis of the 5-Fluoro-4-hydroxypentyl Side Chain Metabolites of Synthetic Cannabinoids 5F-APINACA and CUMYL-5F-PINACA." Synthesis 50, no. 23 (2018): 4683–89. http://dx.doi.org/10.1055/s-0037-1609914.

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An efficient method for the construction of the 5-fluoro-4-hydroxypentyl side chain common to a number of synthetic cannabinoid metabolites was developed. A series of hydroxyl protecting groups was examined to assess the viability as orthogonal protecting groups for epoxidation and regioselective hydrofluorination. The 1-[5-fluoro-4-(diphenyl-tert-butylsilyloxy)]pentyl tosylate was prepared in 67% overall yield (six steps) from pent-4-en-1-ol and was employed for the synthesis of the 4-hydroxy metabolites of the synthetic cannabinoid 5F-APINACA and CUMYL-5F-PINACA.

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37

Hazer, Baki. "Amphiphilic Poly(3-hydroxy alkanoate)s: Potential Candidates for Medical Applications." International Journal of Polymer Science 2010 (2010): 1–8. http://dx.doi.org/10.1155/2010/423460.

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Poly(3-hydroxy alkanoate)s, PHAs, have been very attractive as biomaterials due to their biodegradability and biocompatibility. These hydrophobic natural polyesters, PHAs, need to have hydrophilic character particularly for drug delivery systems. In this manner, poly(ethylene glycol) (PEG) and hydrophilic functional groups such as amine, hydroxyl, carboxyl, and sulfonic acid have been introduced into the PHAs in order to obtain amphiphilic polymers. This review involves in the synthesis and characterization of the amphiphilic PHAs.

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38

Jurczak, Janusz, Maciej Majdecki, Patryk Niedbała, and Agata Tyszka-Gumkowska. "Assisted by Hydrogen-Bond Donors: Cinchona Quaternary Salts as Privileged Chiral Catalysts for Phase-Transfer Reactions." Synthesis 53, no. 16 (2021): 2777–86. http://dx.doi.org/10.1055/a-1472-7999.

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AbstractThis short review is devoted to asymmetric phase-transfer reactions that employ hybrid ammonium Cinchona catalysts supported by possessing hydrogen-bond donor groups. We present recent advances utilizing this type of catalyst in the field of biphasic reaction systems. The main emphasis is placed on the advantages of additional functional groups present in the structure of the catalyst, such as hydroxy, amide, (thio)urea or squaramide.1 Introduction2 Phase-Transfer Hybrid Cinchona Catalysts with a Free Hydroxy Group3 (Thio)urea Hybrid Cinchona Catalysts4 Hybrid Amide-Based Catalysts Bearing a Cinchona Scaffold5 Conclusions

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39

Heinemann, Frank W., Alberto Herrera, Giuseppe Agrifoglio, Romano Dorta, and Jesús Pastrán. "(4R)-3-Hydroxy-7-isopropyl-4-methyl-5,6-dihydrobenzofuran-2(4H)-one." Acta Crystallographica Section E Structure Reports Online 70, no. 7 (2014): o824. http://dx.doi.org/10.1107/s1600536814014524.

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In the title compound, alternatively called α-hydroxy-γ-alkylidenebutenolide, C12H16O3, two independent molecules (AandB) crystallize in the asymmetric unit in each of which the 5,6-dihydrobenzo ring has an envelope conformation. The torsion angle along the butadiene chain in the γ-alkylidenebutenolide core is −177.9 (2)° for moleculeAand 179.9 (2)° for moleculeB. In the crystal, O—H...O hydrogen bonds between hydroxyl and carbonyl groups of adjacent independent molecules form dimers withR22(10) loops.

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40

Ben, Haoxi, Fengze Wu, Zhihong Wu, Guangting Han, Wei Jiang, and Arthur J. Ragauskas. "A Comprehensive Characterization of Pyrolysis Oil from Softwood Barks." Polymers 11, no. 9 (2019): 1387. http://dx.doi.org/10.3390/polym11091387.

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Pyrolysis of raw pine bark, pine, and Douglas-Fir bark was examined. The pyrolysis oil yields of raw pine bark, pine, and Douglas-Fir bark at 500 °C were 29.18%, 26.67%, and 26.65%, respectively. Both energy densification ratios (1.32–1.56) and energy yields (48.40–54.31%) of char are higher than pyrolysis oils (energy densification ratios: 1.13–1.19, energy yields: 30.16–34.42%). The pyrolysis oils have higher heating values (~25 MJ/kg) than bio-oils (~20 MJ/kg) from wood and agricultural residues, and the higher heating values of char (~31 MJ/kg) are comparable to that of many commercial coals. The elemental analysis indicated that the lower O/C value and higher H/C value represent a more valuable source of energy for pyrolysis oils than biomass. The nuclear magnetic resonance results demonstrated that the most abundant hydroxyl groups of pyrolysis oil are aliphatic OH groups, catechol, guaiacol, and p-hydroxy-phenyl OH groups. The aliphatic OH groups are mainly derived from the cleavage of cellulose glycosidic bonds, while the catechol, guaiacol, and p-hydroxy-phenyl OH groups are mostly attributed to the cleavage of the lignin β–O-4 bond. Significant amount of aromatic carbon (~40%) in pyrolysis oils is obtained from tannin and lignin components and the aromatic C–O bonds may be formed by a radical reaction between the aromatic and aliphatic hydroxyl groups. In this study, a comprehensive analytical method was developed to fully understand and evaluate the pyrolysis products produced from softwood barks, which could offer valuable information on the pyrolysis mechanism of biomass and promote better utilization of pyrolysis products.

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41

Hu, Xiaoyun, Jianxin Guo, Cui Wang, Rui Zhang, and Victor Borovkov. "Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups." Beilstein Journal of Organic Chemistry 16 (July 31, 2020): 1875–80. http://dx.doi.org/10.3762/bjoc.16.155.

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To develop new efficient stereoselective catalysts for Biginelli-like reactions, a chiral phosphoric acid bearing two hydroxy groups derived from ʟ-tartaric acid was successfully synthesized via highly regioselective transformations of enantiopure 1,1,4,4-tetraphenylbutanetetraol. The obtained catalyst effectively catalyzed Biginelli-like reactions with moderate to good enantioselectivities. Control experiments indicated that the presence of the two hydroxy groups were indispensable for achieving a high enantioselectivity.

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42

Eraghi Kazzaz, Armin, Zahra Hosseinpour Feizi, and Pedram Fatehi. "Grafting strategies for hydroxy groups of lignin for producing materials." Green Chemistry 21, no. 21 (2019): 5714–52. http://dx.doi.org/10.1039/c9gc02598g.

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43

Badi, Nezha, та Philippe Guégan. "Per-O-(3-hydroxy)propyl-β-cyclodextrin: a cyclodextrin derivative bearing only primary hydroxyl groups". Carbohydrate Research 342, № 14 (2007): 1989–91. http://dx.doi.org/10.1016/j.carres.2007.06.013.

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44

Rosa, Gonçalo P., Ana M. L. Seca, Maria do Carmo Barreto, Artur M. S. Silva, and Diana C. G. A. Pinto. "Chalcones and Flavanones Bearing Hydroxyl and/or Methoxyl Groups: Synthesis and Biological Assessments." Applied Sciences 9, no. 14 (2019): 2846. http://dx.doi.org/10.3390/app9142846.

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Chalcones and flavanones are isomeric structures and also classes of natural products, belonging to the flavonoid family. Moreover, their wide range of biological activities makes them key scaffolds for the synthesis of new and more efficient drugs. In this work, the synthesis of hydroxy and/or methoxychalcones was studied using less common bases, such as sodium hydride (NaH) and lithium bis(trimethylsilyl)amide (LiHMDS), in the aldol condensation. The results show that the use of NaH was more effective for the synthesis of 2′-hydroxychalcone derivatives, while LiHMDS led to the synthesis of polyhydroxylated chalcones in a one-pot process. During this study, it was also possible to establish the conditions that favor their isomerization into flavanones, allowing at the same time the synthesis of hydroxy and/or methoxyflavanones. The chalcones and flavanones obtained were evaluated to disclose their antioxidant, anticholinesterasic, antibacterial and antitumor activities. 2′,4′,4-Trihydroxychalcone was the most active compound in terms of antioxidant, anti-butyrylcholinesterase (IC50 26.55 ± 0.55 μg/mL, similar to control drug donepezil, IC50 28.94 ± 1.76 μg/mL) and antimicrobial activity. 4′,7-Dihydroxyflavanone presented dual inhibition, that is, the ability to inhibit both cholinesterases. 4′-Hydroxy-5,7-dimethoxyflavanone and 2′-hydroxy-4-methoxychalcone were the compounds with the best antitumor activity. The substitution pattern and the biological assay results allowed the establishment of some structure/activity relationships.

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45

Otmar, Miroslav, Milena Masojídková, Ivan Votruba, and Antonín Holý. "An Alternative Synthesis of HPMPC and HPMPA Diphosphoryl Derivatives." Collection of Czechoslovak Chemical Communications 66, no. 3 (2001): 500–506. http://dx.doi.org/10.1135/cccc20010500.

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In (S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine (HPMPC) and (S)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine (HPMPA) with 3-hydroxy functions protected with 4,4'-dimethoxytrityl (DMTr) groups, phosphonate groups were transformed to the morpholides and treated with bis(tributylammonium) diphosphate. Selective cleavage of the DMTr group in the presence of the labile diphosphate residue was achieved in water at pH 2.5. Purification by charcoal adsorption followed by anion exchange chromatography afforded phosphonate-diphosphate compounds (HPMPCpp, HPMPApp).

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46

Prasetyastuti, Dianandha Septiana Rubi, Abrory Agus Cahya Pramana, and Ahmad Hamim Sadewa. "Correlation between ratio of Nrf2/Keap1 and catalase gene expression in liver of hyperlipidemic rats after administration of 7-hydroxy-2-(4-hydroxy- 3-methoxyphenyl)-chromen-4-one." Journal of the Medical Sciences (Berkala Ilmu Kedokteran) 51, no. 1 (2019): 24. http://dx.doi.org/10.19106/jmedscie/005101201903.

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Hyperlipidemia results in excessive superoxide anion radicals that are the cause ofoxidative stress. Phytochemical compounds can reduce oxidative stress. The aim of thisstudy was to investigate the correlations between ratio of Nrf2/Keap1 and catalase geneexpression in livers of hyperlipidemic rats after administration of 7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-chromen-4-one. Twenty-four Rattus norvegicus rats, aged 8 weeks andweighing an average of 200 g were randomly divided into 6 groups i.e. Group 1 wasnormal group (N), Group 2 was hyperlipidemic rats (HL), Group 3 was hyperlipidemicrats with simvastatin (HL+SV), and Groups 4-6 were hyperlipidemic rats with 7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-chromen-4-one doses 10 mg (HL+10), 30 mg (HL+30) or 90 mg/200 g BW (HL+90), respectively, administered orally by gavages. At the end ofthe study, the rats were euthanized and the livers were used to analyze the ratio of Nrf2/Keap 1 and catalase gene expression. Nrf2/Keap1 ratio and catalase gene expressionbetween groups were analyzed by Kruskal Wallis test. Spearman’s correlation test wasused to analyze the correlations between Nrf2/Keap1 ratio and catalase gene expression.The administration of 3 different doses of 7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-chromen-4-one on hyperlipidemic rats increased catalase gene expression. There wasno correlation between ratio Nrf2/Keap1 and catalase gene expression. In conclusion,administration of 7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-chromen-4-one can improvecatalase gene expression in hyperlipidemic rats. However, there is no correlation betweenthe ratio of Nrf2/Keap1 gene expression and the catalase gene expression.

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47

Takano, Seiichi, Ayako Kurotaki, Yoshinori Sekiguchi, Shigeki Satoh, Michiyasu Hirama, and Kunio Ogasawara. "Selective Manipulation of Hydroxy Groups in (2S,3S)-Threitol." Synthesis 1986, no. 10 (1986): 811–17. http://dx.doi.org/10.1055/s-1986-31788.

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48

Kiss, Tamás, Csaba Simon, and Zsolt Vachter. "Copper(II) Complexes of Ligands Containing Alcoholic Hydroxy Groups." Journal of Coordination Chemistry 16, no. 3 (1987): 225–36. http://dx.doi.org/10.1080/00958978708081206.

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49

Togo, Hideo, Sou Matsubayashi, Osamu Yamazaki, and Masataka Yokoyama. "Deoxygenative Functionalization of Hydroxy Groups via Xanthates with Tetraphenyldisilane." Journal of Organic Chemistry 65, no. 9 (2000): 2816–19. http://dx.doi.org/10.1021/jo991715r.

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50

Matsuoka, Koji, Yoko Shiraishi, Daiyo Terunuma та Hiroyoshi Kuzuhara. "Regioselective synthesis of methylated β-cyclodextrins leaving hydroxy groups". Tetrahedron Letters 42, № 8 (2001): 1531–33. http://dx.doi.org/10.1016/s0040-4039(00)02276-0.

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