Carnaubadiol, a triterpene from carnauba wax

1965 ◽  
Vol 18 (9) ◽  
pp. 1411 ◽  
Author(s):  
CS Barnes ◽  
MN Galbraith ◽  
E Ritchie ◽  
WC Taylor
Keyword(s):  
Hydroxyl Group ◽  
Side Chain ◽  
Spectroscopic Methods ◽  
Carnauba Wax ◽  
Group A ◽  
Tertiary Hydroxyl

By chemical and spectroscopic methods, carnaubadiol, C31H54O2, a constituent of carnauba wax, was shown to contain one secondary and one tertiary hydroxyl group, and one isopropenyl group. A series of degradative reactions yielded a heptanorketone, identical with the known 3β-acetoxyhexanordammaran-20-one, previously obtained from dammarenediol. The structure and configuration of the side-chain were established by oxidation of dihydrocarnaubadiol to the known (-)-(S)-5,6-dimethylheptan-2-one. Carnaubadiol was thus shown to be 24β-methyl- dammar-25-ene-3β,20ξ-diol.

Zur Chemie des Phorbols, VIII

1968 ◽  
Vol 23 (12) ◽  
pp. 1584-1597 ◽  
Author(s):  
Michael Gschwendt ◽  
Erich Hecker
Keyword(s):  
Allyl Alcohol ◽  
Lead Tetraacetate ◽  
Hydroxyl Group ◽  
Structural Elements ◽  
Complete Structure ◽  
Relative Configuration ◽  
Alcohol Group ◽  
Partial Structures ◽  
Group A ◽  
Tertiary Hydroxyl

Oxidation of phorbol with one mole of lead tetraacetate yields bisdehydrophorbol, tiglophorbol and small amounts of phorbolacton-semiacetal. By chemical and spectroscopic investigations of bisdehydrophorbol and its derivatives its complete structure 16 is derived based upon the partial structures and structural elements of phorbol (1 - 3) which have been deduced in preceding communications. By consideration of the mechanism of the oxidative scission of the cyclopropanol unit in phorbol the structure 15 of this new tetracyclic diterpene is obtained. 15 has a pentamethyl-tetradecahydro-1H-cyclopropabenzazulene skeleton (tiglian) carrying as functional groups a tertiary hydroxyl group, an α,β-unsaturated tertiary 1.2-ketol group, a primary allyl alcohol group and a α- [hydroxycyclopropyl] -carbinol group. Phorbol is 4.9.12β.13.20-pentahydroxy-tigliadien- (1.6) -on- (3) (15) , bisdehydrophorbol 4.9.12β.20-tetrahydroxy-13.15-seco-tigliatrien- (1.6.15) -dion- (3.13) (16) the conformations of which have been determined. The structure of phorbolacton-semiacetal is determined in the following communication of this series. Based upon the structure of phorbol and additional chemical and spectroscopic evidence the structure of tiglophorbol (17) is also derived. With the data provided the relative configuration and the conformation of six out of the eight asymmetric centers of phorbol is determined.

LYCOPODIUM ALKALOIDS: XVI. ANNOTINE

1964 ◽  
Vol 42 (11) ◽  
pp. 2584-2594 ◽  
Author(s):  
W. A. Szarek ◽  
K. A. H. Adams ◽  
M. Curcumelli-Rodostamo ◽  
D. B. MacLean
Keyword(s):  
Double Bond ◽  
Nitrogen Atom ◽  
Hydroxyl Group ◽  
Tertiary Nitrogen Atom ◽  
Chemical Studies ◽  
Group A ◽  
Instrumental Methods ◽  
Tertiary Hydroxyl ◽  
Plausible Structure ◽  
Tertiary Nitrogen

Annotine, C16H21O3N, is shown to be pentacyclic and to contain a tertiary hydroxyl group, a lactone function, a tertiary nitrogen atom, and a dialkylated double bond. The position of the double bond and the tertiary hydroxyl group relative to the nitrogen atom has been established by Emde degradation of annotine methiodide. The presence of a lactone function is inferred from the reduction of annotine to dihydroannotinol, a hemiacetal, which reacts with 1 mole of ethyl mercaptan. The reduction of the lactone to a diol in an annotine derivative has been carried out. The chemical studies and the examination of annotine and its derivatives by modern instrumental methods allow the assignment of a plausible structure to the alkaloid.

Transformations of Steroids by Beauveria bassiana

2005 ◽  
Vol 60 (1-2) ◽  
pp. 103-108 ◽  
Author(s):  
Ewa Huszcza ◽  
Jadwiga Dmochowska-Gładysz ◽  
Agnieszka Bartmańska
Keyword(s):  
Double Bond ◽  
Beauveria Bassiana ◽  
Hydroxyl Group ◽  
Side Chain ◽  
Double Bonds ◽  
Methyl Group ◽  
Group Reduction ◽  
Group A ◽  
Acetyl Group

The course of transformations of testosterone and its derivatives, including compounds with an additional C1,C2 double bond and/or a 17α-methyl group, a 17β-acetyl group or without a 19-methyl group, by a Beauveria bassiana culture was investigated. The fungi promoted hydroxylation of these compounds at position 11α, oxidation of the 17β-hydroxyl group, reduction of the C1,C2 or C4,C5 double bonds and degradation of the progesterone side-chain, leading to testosterone. The structure of 4-ene-3-oxo-steroids had no influence on regio- and stereochemistry of hydroxylation. In a similar manner, dehydroepiandrosterone was hydroxylated by Beauveria bassiana at position 11α, however, a small amount of 7α- hydroxylation product was also formed.

Dehydration and Stabilization of a Reactive Tertiary Hydroxyl Group in Solid Oral Dosage Forms of BMS-779788

2016 ◽  
Vol 105 (4) ◽  
pp. 1478-1488 ◽  
Author(s):  
Monica L. Adams ◽  
Vijayata Sharma ◽  
Madhushree Gokhale ◽  
Yande Huang ◽  
Kevin Stefanski ◽  
...  
Keyword(s):  
Dosage Forms ◽  
Oral Dosage ◽  
Hydroxyl Group ◽  
Solid Oral Dosage Forms ◽  
Oral Dosage Forms ◽  
Tertiary Hydroxyl

17α-HYDROXYLASE DEFICIENCY. A COMBINATION OF HYDROXYLATION DEFECT AND REVERSIBLE BLOCKADE IN ALDOSTERONE BIOSYNTHESIS

1979 ◽  
Vol 90 (3) ◽  
pp. 490-504 ◽  
Author(s):  
D. R. Rovner ◽  
J. W. Conn ◽  
E. L. Cohen ◽  
F. G. Berlinger ◽  
D. C. Kern ◽  
...  
Keyword(s):  
Plasma Concentration ◽  
Extracellular Fluid ◽  
Plasma Renin ◽  
Hydroxyl Group ◽  
Side Chain ◽  
Hydroxylase Deficiency ◽  
Resultant Increase

ABSTRACT We have studied the hormonal secretion and excretion patterns in a patient with the XX type of 17α-hydroxylase deficiency. In the untreated state, the patient's urine contained only those steroids which do not require 17-hydroxylation in their biosynthesis. Aldosterone was not produced in the patient and the metabolic product of its immediate precursor, 18-hydroxy-11-dehydro-tetrahydrocorticosterone, was excreted in markedly elevated amounts. This apparent complete block in 18 oxidation was reversible upon long-term ACTH suppression within 27 days. Direct in vitro incubation of the patient's adrenal gland removed at operation demonstrated, 1) the complete lack of 17α-hydroxylase activity, 2) the functional block in the ability to oxidize the hydroxyl group at the 18 methyl side chain. The addition of physiological concentrations of angiotensin to the incubation medium further showed, 3) angiotensin mildly stimulated the entire aldosterone biosynthetic pathway, 4) angiotensin directly stimulated the conversion of 18-hydroxycorticosterone to aldosterone. We propose that in this patient, 17-hydroxylase deficiency produced a decreased plasma concentration of cortisol, followed by stimulation of deoxycorticosterone production by ACTH. The resultant increase in extracellular fluid volume suppressed plasma renin activity. This resulted in a low plasma concentration of angiotensin II which directly suppressed oxidation of 18-hydroxycorticosterone to aldosterone. This defect has been called corticosterone methyl oxidase defect type 2.

Side Chain Influence on Main Chain Orientation of PPV-Type Oligomers

1999 ◽  
Vol 598 ◽  
Author(s):  
Ruth Müllner ◽  
Laurence Noirez ◽  
Egbert Zojer ◽  
Franz Stelzer ◽  
Günther Leising
Keyword(s):  
Magnetic Field ◽  
Neutron Diffraction ◽  
Main Chain ◽  
Side Chain ◽  
Phenylene Vinylene ◽  
Spectroscopic Methods ◽  
Polarized Optical Microscopy ◽  
Chain Orientation ◽  
H Nmr ◽  
Ft Ir

ABSTRACTOligo (p-phenylene vinylene)s OPV were synthesized having cyanobiphenyloxy-groups bonded to the vinylene double bonds via alkylene spacers. A Pd(0)-reaction was used to synthesize the oligomers starting with the dibromo-substituted benzene and the alkenyloxy-biphenyl-nitrile. The orientation of the mesogens by a magnetic field and their influence on the orientation of the main chain was investigated by means of neutron diffraction ND. Data on the photophysics of the oligomers were gained using several spectroscopic methods such as UV/VIS, polarized optical microscopy POM, SEC, 1H-NMR, FT-IR.

scholarly journals Preparation of side chain liquid crystal polyether chelating resin and its adsorption properties for Cu2+ in water

2021 ◽  
Author(s):  
Chaoyi Qian ◽  
Meng Li ◽  
Shuang Wang ◽  
Qing Gao ◽  
Huaiwei Yao ◽  
...  
Keyword(s):  
Liquid Crystal ◽  
Influence Factors ◽  
Chelating Resin ◽  
Side Chain ◽  
Order Kinetic ◽  
Adsorption Model ◽  
Order Kinetic Model ◽  
Group A ◽  
New Type ◽  
Cationic Ring Opening Polymerization

Abstract With epoxycyclohexane as critical modifying monomer, the copolyether was obtained by cationic ring-opening polymerization of epichlorohydrin and epoxycyclohexane. Then biphenyl was used as the mesogen, and diglycolamidic acid was used as the terminal chelating group, a new type of side chain liquid crystal polyether chelating resin was prepared at last. The adsorption influence factors, reuse performance, adsorption model and adsorption kinetics of the chelated resin on Cu 2+ in water were studied systematically. The results showed that the resin has good adsorption and reuse performance for the treatment of Cu 2+ in water, and the adsorption of Cu 2+ is Langmuir monolayer adsorption, and the adsorption process conforms to a quasi-second-order kinetic model. The adsorption performances of the chelated resin has great potential for recovery of copper resource from non-ferrous smelting industry.

scholarly journals Studies on the Antibacterial Influence of Two Ionic Liquids and their Corrosion Inhibition Performance

2020 ◽  
Vol 10 (4) ◽  
pp. 1444 ◽  
Author(s):  
Mohamed F. Shehata ◽  
Ashraf M. El-Shamy ◽  
Khaled M. Zohdy ◽  
El-Sayed M. Sherif ◽  
Sherif Zein El Abedin
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Synergistic Effect ◽  
Corrosion Inhibition ◽  
Hydroxyl Group ◽  
Side Chain ◽  
Imidazolium Cation ◽  
Corrosion Effect ◽  
Inhibition Performance

In this paper the anti-bacterial and the anti-corrosion effect of two different ionic liquids, namely 1-(2-hydroxyethyl)-3-methylimidazolinium chloride ([OH-EMIm]Cl) and 1-ethyl-3-methyleimidazolinium chloride ([EMIm]Cl) was demonstrated. The results revealed that the corrosion inhibition influence of the ionic liquid [OH-EMIm]Cl is higher than that of the ionic liquid [EMIm]Cl. Furthermore, the ionic liquid [OH-EMIm]Cl showed better biocidal influence compared with the ionic liquid [EMIm]Cl. This indicates the synergistic effect due to the incorporation of the hydroxyl group into the side chain of the imidazolium cation leading to enhanced antibacterial and anticorrosion effect.

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