Oxyzimtalkohole und ihre Dehydrierungs‐polymerisate

Freudenberg, Karl; Hübner, Hans Hugo

doi:10.1002/cber.19520851213

Cited by 149 publications

(45 citation statements)

References 19 publications

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“…Recrystallization from 1,2-dichloroethane provided white needles of melting point 74.5-75°(corrected); (ref. 10 Abbreviations: PMR, proton magnetic resonance; NMR, nuclear magnetic resonance; UV, ultraviolet; IR, infrared; MW, molecular weight.…”

mentioning

confidence: 99%

“…At various time intervals the CO2 traps were acidified with 6 ml of 2 N H2SO4 and sparged with air to transfer the 14CO2 into scintillation vials that contained 10 all yields of 46, 31, and 32% from vanillin methoxymethyl ether, phenol, and guaiacol, respectively. Polymerization of the labeled coniferyl alcohols gave synthetic lignins in quantitative yields with specific activities of 1.8 X 105, 1.4 X 10 , and 7.8 X 104 dpm/mg for the side-chain-, ring-, and methoxy-labeled polymers, respectively.…”

mentioning

confidence: 99%

“…Number average molecular weight (Ml,) was determined by vapor pressure osmometry at 370 with dimethylformamide as solvent (19) Aqueous lignin suspensions (10-100 gl) containing [10][11][12][13][14][15][16][17][18][19][20] mg/ml were added to 10 ml of scintillation fluid consisting of 10 These wood-destroying fungi were incubated with the labeled lignins in closed 125 ml erlenmeyer flasks that contained 2 g of a 1:1 mixture of ground aspen and spruce wood (20 mesh = 7.9 openings/cm), 2 ml of a filter-sterilized basal medium (below), and 3 ml of lignin suspension (640 Ig, 5 X 104 dpm). Lignins in dimethylformamide solution (20-30 mg/ml) were added aseptically to sterile distilled water to give a fine suspension; no contamination problem was encountered.…”

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confidence: 99%

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Preparation and microbial decomposition of synthetic [14C]ligins.

Kirk¹,

Connors²,

Bleam³

et al. 1975

Proc. Natl. Acad. Sci. U.S.A.

200

113

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A definitive assay for microbiological and biochemical research on the biodegradation of lignin was developed using radioactive synthetic lignins specifically labeled in the side chains, aromatic rings or in the methoxyl groups. The [14C]lignins were prepared by oxidative polymerization with peroxidase and H2O2 Of specifically labeled coniferyl alcohol (4-hydroxy-3-methyoxycinnamyl alcohol). The synthetic polymers were shown by spectroscopic and chemical methods to contain the same intermonomer linkages found in natural lignins. Incubation of the [14C]lignins with known lignin-degrading fungi and with a forest soil resulted in 14CO2 evolution.

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Preparation and microbial decomposition of synthetic [14C]ligins.

Kirk¹,

Connors²,

Bleam³

et al. 1975

Proc. Natl. Acad. Sci. U.S.A.

200

113

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“…Prepared from 4′-chloro-3-hydroxyflavone (2a) and Oacetylsyringoyl chloride (Freudenberg & Hüber, 1952 Acetylsyringic acid 3′,4′-dichloroflavon-3-yl ester (3d)…”

Section: Acetylsyringic Acid 4′-chloroflavon-3-yl Ester (3c)mentioning

confidence: 99%

“…Obtained from the reaction of 4′-chloro-3-hydroxyflavone (2a) with triacetylgalloyl chloride (Freudenberg & Hüber, 1952 …”

Section: -Acetoxy-4′-chloroflavone (6a)mentioning

confidence: 99%

Synthesis and Anti-Human Immunodeficiency Virus Type 1 Integrase Activity of Hydroxybenzoic and Hydroxycinnamic Acid Flavon-3-yl Esters

Desideri

Sestili

Stein

et al. 1998

Antivir Chem Chemother

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A series of new hydroxybenzoic and hydroxycinnamic acid flavon-3-yl esters were synthesized in order to obtain compounds targeting the human immunodeficiency virus (HIV) type 1 integrase (IN). The esters were tested for anti-IN and anti-reverse transcriptase (RT) activity in enzyme assays and for anti-HIV-1, anti-proliferative and anti-topoisomerase activity in cell-based assays. In enzyme assays, the two gallic acid flavon-3-yl esters showed a notable IN inhibition (IC 50 values were 8.3 and 9.1 µM, respectively), while the two caffeic acid flavon-3-yl esters exhibited a modest activity (IC 50 75 and 60 µM, respectively). Replacement of hydroxyl groups resulted in loss of potency. Caffeic acid 3′,4′-dichloroflavon-3-yl ester also inhibited the RT activity whereas it was not active on human topoisomerases. It therefore represents an interesting example of a compound specifically targeting more than one step of the virus replication cycle.

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Hydroxybenzaldehydes

Maliverney¹,

Mulhauser²

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Among the hydroxybenzaldehydes, only mono‐, di‐ and trihydroxybenzaldehydes are known. Salicylaldehyde (2‐hydroxybenzaldehyde) and 4‐hydroxybenzaldehyde represent more than 99% of the hydroxybenzaldehydes' market. The physical and chemical properties of hydroxybenzaldehydes are described. 2‐Hydroxy and 4‐hydroxybenzaldehydes react in a similar manner as phenol toward electrophiles. The aldehyde function can be reduced or oxidized to form a variety of compounds depending on the reagents and conditions used. Hydroxybenzaldehydes undergo the normal reactions of aromatic aldehydes. Most industrial methods for the manufacture of hydroxybenzaldehydes are based on phenol, but other routes exist, starting from hydroxybenzoic acids, by reduction, or from cresols, by oxidation. Both p ‐hydroxybenzaldehyde and salicylaldehyde have a low to moderate acute oral toxicity, but salicylaldehyde is, in addition, corrosive toward skin and appreciably irritating to the eyes. The hydroxybenzaldehydes are used primarily as chemical intermediates to a variety of products. The largest single use of salicylaldehyde is in the manufacture of coumarin. Both are used as intermediates in the synthesis of agrochemicals, pharmaceuticals, fragrances, and in electroplating. Condensation products of salicylaldehyde and diamines have important chelation properties, and have wide use in the stabilization of petroleum products, and in chemical processing, especially as oxidation catalysts. These and other applications to polymer chemistry are described.

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Oxyzimtalkohole und ihre Dehydrierungs‐polymerisate

Cited by 149 publications

References 19 publications

Preparation and microbial decomposition of synthetic [14C]ligins.

Preparation and microbial decomposition of synthetic [14C]ligins.

Synthesis and Anti-Human Immunodeficiency Virus Type 1 Integrase Activity of Hydroxybenzoic and Hydroxycinnamic Acid Flavon-3-yl Esters

Hydroxybenzaldehydes

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