The Ultraviolet-induced Isomerization of Tiglic Acid to Angelic Acid

1952 ◽  
Vol 74 (24) ◽  
pp. 6292-6293 ◽  
Author(s):  
S. W. Pelletier ◽  
William L. McLeish
Keyword(s):  
Tiglic Acid ◽  
Angelic Acid

Biosynthesis of the tiglic acid moiety of meteloidine in

1967 ◽  
Vol 8 (18) ◽  
pp. 1727-1730 ◽  
Author(s):  
Edward Leete ◽  
J.Brendan Murrill
Keyword(s):  
Acid Moiety ◽  
Tiglic Acid

scholarly journals The Synthesis of Cinchonine Tiglat Ester Compound and Cytotoxic Test Against MCF-7 Breast Cancer Cell

2018 ◽  
Vol 19 (2) ◽  
pp. 54-61
Author(s):  
Ahmad Khanifudin ◽  
Gian Primahana ◽  
Sylvia Rizky Prima ◽  
Puspa Dewi Lotulung ◽  
Muhammad Hanafi
Keyword(s):  
Breast Cancer ◽  
Cancer Cells ◽  
Breast Cancer Cells ◽  
Cinchona Alkaloid ◽  
Alamar Blue ◽  
Tiglic Acid ◽  
Spectroscopy Instrumentation ◽  
Ic50 Value ◽  
Pass Through ◽  
Mcf 7

Cinchonine is a type of cinchona alkaloid compound commonly found and/or isolated from Cinchona sp. plant. It is commonly used to treat malaria, and can potentially be used against cancer cells. In this particular study, cinchonine ester derivatives were extracted through esterification processs. Synthesized esther is aimed to gain higher lipophilicity of cinchonine so that makes it easier to pass through cell membrane. Esterification was done using DCC activator as well as DMAP catalyst with tiglic acid used to create cinchonine tiglat. Subsequent cinchonine tiglat was obtained in the form of oil with 25,28% yield. The compound obtained from the synthesis was the analyzed using LC-ESI-MS and 1H-NMR spectroscopy instrumentation. Results show that the target compound has been successfully synthesized. Its cytotoxic ability against MCF-7 breast cancer cells was tested using the Alamar Blue method. Results concluded that cinchonine tiglat ester compound has a viable cytotoxic activity with IC50 value of 1.22 ppm.

scholarly journals Tiglicaciduria in propionicacidaemia

1972 ◽  
Vol 126 (4) ◽  
pp. 1035-1037 ◽  
Author(s):  
William L. Nyhan ◽  
Toshiyuki Ando ◽  
Karsten Rasmussen ◽  
William Wadlington ◽  
Anthony W. Kilroy ◽  
...  
Keyword(s):  
Human Body ◽  
Body Fluids ◽  
Tiglic Acid

Tiglic acid, which has not previously been found in human body fluids, was recently detected in the urine of two patients with propionicacidaemia. These patients had a documented defect in the oxidation of propionate. A competition between acrylyl-CoA and tiglyl-CoA for crotonase could explain the accumulation of tiglic acid.

The Encephalopathic Action of Five-carbon-atom Fatty Acids in the Rabbit

1976 ◽  
Vol 50 (6) ◽  
pp. 463-472 ◽  
Author(s):  
P. F. Teychenne ◽  
I. Walters ◽  
L. E. Claveria ◽  
D. B. Calne ◽  
Jane Price ◽  
...  
Keyword(s):  
Carbon Atom ◽  
Functional Group ◽  
Low Frequency ◽  
Isovaleric Acid ◽  
Valeric Acid ◽  
Inborn Errors ◽  
Pronounced Increase ◽  
Tiglic Acid ◽  
Ventriculocisternal Perfusion ◽  
Electroencephalographic Recording

1. Five-carbon-atom organic acids (C-5 acids) have been administered intravenously to rabbits with ventriculocisternal perfusion and continuous electroencephalographic recording (EEG). The concentration of the acids in the cerebrospinal fluid (CSF) perfusate have been compared with changes in integrated low-frequency activity in the EEG. 2. The C-5 acids investigated were those accumulating in inborn errors of metabolism, i.e. isovaleric acid, β-methylcrotonic acid, tiglic acid and α-keto- and α-hydroxy-isovaleric acid. Their activity was compared with that of valeric acid. 3. Valeric acid and isovaleric acid produced coma and pronounced increase in slow-wave electrical activity and these changes paralleled the increase in concentration of the acids in the CSF perfusate. 4. The concentration of β-methylcrotonic acid and tiglic acid in the CSF perfusate reached values comparable with valeric acid and isovaleric acid but showed less encephalopathic activity. An interaction between β-methylcrotonic acid and isovaleric acid was observed. 5. Although the concentrations of α-ketoisovaleric acid and α-hydroxyisovaleric acid rose to the lesser extent in the CSF perfusate, changes in reusability of the animal and in the EEG recording were demonstrated. 6. It is concluded that all the C-5 acids tested have encephalopathic activity although this is lessened by the presence of either a double bond or an oxygenated functional group.

Application of [Ru((R)-BINAP)(MeCN)(1-3:5,6-η-C8H11)](BF4) as a catalyst precursor for enantioselective hydrogenations

1998 ◽  
Vol 76 (10) ◽  
pp. 1447-1456 ◽  
Author(s):  
Christopher JA Daley ◽  
Jason A Wiles ◽  
Steven H Bergens
Keyword(s):  
Carboxylic Acid ◽  
Type Systems ◽  
Enantioselective Hydrogenation ◽  
Catalyst System ◽  
Structural Features ◽  
Catalyst Precursor ◽  
Unsaturated Carboxylic Acid ◽  
Tiglic Acid ◽  
Protic Solvents ◽  
Acid Methyl

A catalyst system employing [Ru((R)-BINAP)(MeCN)(1-3:5,6-η-C8H11)](BF4) as catalyst precursor was evaluated using the enantioselective hydrogenations of tiglic acid, α-acetamidocinnamic acid, itaconic acid, methyl tiglate, dimethyl itaconate, geraniol, ethyl acetoacetate, and dimethyl oxaloacetate as a series of typical substrates. Acetone and MeOH were used as model aprotic and protic solvents, respectively. The hydrogenation of substrates containing an α, β-unsaturated carboxylic acid functionality required stoichiometric quantities of NEt3 to occur at reasonable rates in acetone solution, while in MeOH solution it did not. The enantioselectivities were typically higher in acetone than in MeOH. This catalyst system is among the more enantioselective ruthenium-BINAP type systems reported for the catalytic hydrogenation of substrates containing an α, β-unsaturated acid or ester functionality. The enantioselectivities for the hydrogenation of ketones ranged from poor (15%) to moderate (74%). 1,4-Dicarboxylate substrates with the prochiral olefin or ketone at the 2-position were all hydrogenated in good to high ee with the same enantioface selectivity both with our system and other catalysts reported in the literature. This raised the possibility that these substrates were hydrogenated through intermediates with similar structural features. Key words: ruthenium, BINAP, enantioselective, hydrogenation, catalysis.

Sign in / Sign up

Export Citation Format

Share Document