scholarly journals The metabolism of 3,5-di-tert.-butyl-4-hydroxytoluene in the rat and in man

1968 ◽  
Vol 106 (4) ◽  
pp. 783-790 ◽  
Author(s):  
J W Daniel ◽  
J C Gage ◽  
D. I. Jones

1. The major metabolites of 3,5-di-tert.-butyl-4-hydroxytoluene (BHT) in the rat are 3,5-di-tert.-butyl-4-hydroxybenzoic acid (BHT-acid), both free (9% of the dose) and as a glucuronide (15%), and S-(3,5-di-tert.-butyl-4-hydroxybenzyl)-N-acetylcysteine. 2. The mercapturic acid does not appear to derive from the usually accepted enzyme mechanism, and may involve a non-enzymic reaction between BHT free radical and cysteine. 3. The ester glucuronide and mercapturic acid found in rat urine are also the major metabolites in rat bile and must be responsible for the enterohepatic circulation. 4. Free BHT-acid is the main component in rat faeces. 5. In man, BHT-acid, free and conjugated, is a minor component in urine, and the mercapturic acid is virtually absent. The bulk of the radioactivity is excreted as the ether-insoluble glucuronide of a metabolite in which the ring methyl group and one tert.-butyl methyl group are oxidized to carboxyl groups, and a methyl group on the other tert.-butyl group is also oxidized, probably to an aldehyde group. 6. These differences in metabolism by the rat and by man are sufficient to account for the difference in excretion by the two species.

1968 ◽  
Vol 109 (5) ◽  
pp. 727-736 ◽  
Author(s):  
Sybil P. James ◽  
D. A. Jeffery ◽  
Rosemary H. Waring ◽  
P. B. Wood

1. Rabbits and rats dosed with 1-bromobutane excrete in urine, in addition to butylmercapturic acid, (2-hydroxybutyl)mercapturic acid, (3-hydroxybutyl)mercapturic acid and 3-(butylthio)lactic acid. 2. Although both species excrete both the hydroxybutylmercapturic acids, only traces of the 2-isomer are excreted by the rabbit. The 3-isomer has been isolated from rabbit urine as the dicyclohexylammonium salt. 3. 3-(Butylthio)lactic acid is formed more readily in the rabbit; only traces are excreted by the rat. 4. Traces of the sulphoxide of butylmercapturic acid have been found in rat urine but not in rabbit urine. 5. In the rabbit about 14% and in the rat about 22% of the dose of 1-bromobutane is excreted in the form of the hydroxymercapturic acids. 6. Slices of rat liver incubated with S-butylcysteine or butylmercapturic acid form both (2-hydroxybutyl)mercapturic acid and (3-hydroxybutyl)mercapturic acid, but only the 3-hydroxy acid is formed by slices of rabbit liver. 7. S-Butylglutathione, S-butylcysteinylglycine and S-butylcysteine are excreted in bile by rats dosed with 1-bromobutane. 8. Rabbits and rats dosed with 1,2-epoxybutane excrete (2-hydroxybutyl)mercapturic acid to the extent of about 4% and 11% of the dose respectively. 9. The following have been synthesized: N-acetyl-S-(2-hydroxybutyl)-l-cysteine [(2-hydroxybutyl)mercapturic acid] and N-acetyl-S-(3-hydroxybutyl)-l-cysteine [(3-hydroxybutyl)mercapturic acid] isolated as dicyclohexylammonium salts, N-toluene-p-sulphonyl-S-(2-hydroxybutyl)-l-cysteine, S-butylglutathione and N-acetyl-S-butylcysteinyl-glycine ethyl ester.


e-CliniC ◽  
2016 ◽  
Vol 4 (1) ◽  
Author(s):  
Marianne C. Jacobus ◽  
Max F.J Mantik ◽  
Adrian . Umboh

Abstract: Haemoglobin is the main component of red blood cells that serves as a transporter of oxygen and carbon dioxide in the blood. The normal range of haemoglobin values can be used to determine the degree of anemia according to age and gender. Geographical condition such as altitude influences the haemoglobin value. This study aimed to obtain the difference of haemoglobin levels between teenagers with good nutrition status who live at the highland and those at the seaside. This was an observational analytical study with a cross sectional design. Samples were students with good nutrition status of SMPN 3 Tomohon (living at the highland) and those of SMP Kristen Nazaret Tuminting (living at the seaside). There were 60 students who met the inclusion criteria as follows: adolescent, good nutrition status, healthy, aged 13-15 years, lived at the highland or at the seaside ≥ 6 month, and willing to be performed blood examinations, and had been approved by their parents. The Mann-Whitney test for the difference between haemoglobin levels of the two groups showed a p value < 0,001. Conclusion: There was a very significant difference between haemoglobin levels of good nutrition teenagers who lived at the highland and at the seaside. Keywords: haemoglobin levels, good nutrition, teenagers, highland, seaside  Abstrak: Hemoglobin merupakan komponen utama sel darah merah dan berfungsi sebagai transporter oksigen dan karbon dioksida dalam darah. Batas normal nilai hemoglobin dapat digunakan untuk menetapkan derajat anemia, dengan distribusi usia dan jenis kelamin spesifik didasarkan pada sampel referensi sehat. Kondisi geografis, seperti ketinggian tempat dari permukaan laut menjadi faktor pertimbangan dalam distribusi nilai normal hemoglobin. Penelitian ini bertujuan untuk mendapatkan perbedaan kadar hemoglobin antara remaja gizi baik yang tinggal di pegunungan dengan yang tinggal di tepi pantai. Jenis penelitian ini analitik-observasional dengan desain potong lintang. Sampel penelitian yaitu remaja gizi baik yang tinggal di pegunungan yaitu siswa SMPN 3 Tomohon dan yang di tepi pantai yaitu siswa SMP Kristen Nazaret Tuminting. Subjek penelitian berjumlah 60 remaja yang memenuhi kriteria inklusi yaitu gizi baik, sehat, berumur 13-15 tahun, berdomisili di pegunungan atau tepi pantai ≥6 bulan, bersedia dilakukan pemeriksaan darah, dan telah disetujui oleh orang tua. Data yang diperoleh dianalisis menggunakan uji Mann-Whitney dengan bantuan program SPSS. Hasil uji Mann-Whitney mengenai perbedaan kadar hemoglobin antara kedua kelompok menunjukkan nila p <0,001. Simpulan: Terdapat perbedaan yang sangat bermakna kadar hemoglobin remaja gizi baik yang tinggal di pegunungan dengan di tepi pantai.Kata kunci: kadar hemoglobin, remaja gizi baik, pegunungan, tepi pantai


2009 ◽  
Vol 92 (5) ◽  
pp. 1336-1342 ◽  
Author(s):  
John C Reepmeyer ◽  
D Andr d'Avignon

Abstract A sildenafil-related compound was detected in an herbal dietary supplement marketed as an aphrodisiac. The compound was identified as an analogue of sildenafil in which the carbonyl group in the pyrimidine ring of sildenafil was substituted with a thiocarbonyl group, and the methyl group on the piperazine ring was substituted with a hydroxyethyl group. Based on this structure, the compound was named thiohydroxyhomosildenafil. The structure of the compound was established using HPLC/MS, UV spectrometry, electrospray ionization-MS/MS, NMR spectrometry, and a hydrolytic process. One key product of hydrolysis was 1-(2-hydroxyethyl)-piperazine; the identification of this product defined the amine portion of the compound. Another key product of hydrolysis was hydroxyhomosildenafil, generated by hydrolysis of the thiocarbonyl group to a carbonyl group (C S C O). Hydroxyhomosildenafil was detected as a minor component in the dietary supplement.


2019 ◽  
Vol 6 (1) ◽  
pp. 3-14 ◽  
Author(s):  
Igor G. Zenkevich ◽  
Nino G. Todua ◽  
Anzor I. Mikaia

Background: Application of simple regularities and general principles along with direct use of reference gas chromatography retention index data for reliable structure determination of compounds can be enhanced by determination of new regularities that are specific to certain structural elements. Objective: Revelation and interpretation of an anomaly in the elution order of alkyl esters of alkoxycarbonyl derivatives of glycine and alanine on standard and semi-standard non-polar phases. Method: Preliminary derivatization of amino acids to alkyl esters of N-alkoxycarbonyl analogs and interpretation of their gas chromatographic characteristics. Results: Alkyl esters of N-alkoxycarbonyl derivatives of alanine (Alkyl = C2H5, n- and iso-C3H7) elute prior to the same derivatives of glycine, despite the presence of an additional methyl group at C(2) in the molecule. Elution order is reversed for methyl esters of N-methoxycarbonyl derivatives. Conclusion: It is established that the peculiar behavior of alkyl esters of N-alkoxycarbonyl derivatives of glycine and alanine agrees with the concepts of gas chromatography and the known retention index regularities of organic compounds. A decrease of retention index values is a result of an introduction of an additional methyl group to a carbon atom connected to two polar fragments in a molecule like CH2XY. The dependence of the difference of retention index values for homologs of the types of CH3-CHXY and CH2XY vs. the total mass of fragments (X + Y) is similar to those for other sub-groups of analytes.


1868 ◽  
Vol 16 ◽  
pp. 144-147

The typical transformation which hydrocyanic acid undergoes when sub­mitted, under appropriate circumstances, to the action of water, is capable of assuming two different forms when accomplished in its homologues. If the hydrocyanic molecule be found to fix the elements of two mole­cules of water, yielding ultimately formic acid and ammonia, it is obvious that the atom group which in the homologues of hydrocyanic acid we as­sume in the place of hydrogen may be eliminated when these homologues are decomposed by water in conjunction either with formic acid or with ammonia. To take an example: —When acting with water upon the sim­plest homologue of hydrocyanic acid (upon cyanide of methyl), we may ex­pect to see the methyl-group separating either in the form of methyl-formic, i. e . acetic acid, or in the form of methyl-ammonia, i. e . of methylamine, The difference of the two reactions and their relation to the metamorphosis of hydrocyanic acid itself are exhibited by the following equations:


1971 ◽  
Vol 125 (2) ◽  
pp. 395-400 ◽  
Author(s):  
P. G. C. Douch ◽  
J. N. Smith

The oxidation of 3,5-di-tert.-butylphenyl N-methylcarbamate (Butacarb) has been studied in the flies Musca domestica and Lucilia sericata, grass grubs Costelytra zealandica and the mouse. In all species eleven oxidation products, which were formed by hydroxylation of the tert.-butyl groups and the N-methyl group, were detected.


2015 ◽  
Vol 44 (5) ◽  
pp. 70-74
Author(s):  
SM Grobler ◽  
MM Scholtz ◽  
JPC Greyling ◽  
FWC Neser

The estimated calving percentage of beef cattle is 62% in the commercial sector of South Africa. Fertility is regarded as the main component influencing total herd efficiency in beef cattle. If the long calving seasons can be shortened and the calving percentage increased, more and heavier calves with a more uniform age can be weaned. Cows calving earlier in the season also have an extended “recovery period” and have the opportunity to calve in a better body condition during the next season, compared to cows calving late in the season. Cows that calve early also have a better chance of conceiving in the next breeding season and are generally seen as the more fertile animals. Research has been undertaken to evaluate the effect of oestrous synchronization followed by natural mating on the calving rate and calving distribution of multiparous beef cows. In this trial Bonsmara cows were mated naturally after synchronization over a period of four years (2009 - 2012) in an extensive production system on natural sour-mixed bushveld. The synchronized cows calved earlier during the 2009 calving season and cows in anoestrus started cycling again. The average days-to-calving after the start of the breeding season was 243 days for the synchronized cows and 267 for the non-synchronized cows. The calves born from the synchronized cows were therefore, on average, 24 days older than the calves born from the non-synchronized cows. From 2010 onwards the difference declined and it seems the biggest effect was obtained during the first year of synchronization.Keywords: Beef cattle, Marikana thorn veld, natural mating, oestrous synchronization


2009 ◽  
Vol 92 (2) ◽  
pp. 487-495 ◽  
Author(s):  
Sujatha Nayak ◽  
Penmatsa Tanuja ◽  
Rao Beedu Sashidhar

Abstract A simple and sensitive indirect noncompetitive enzyme immunoassay to quantitate mercapturic acid-aflatoxin B1 (AFB1) adduct in rat urine is reported. A novel procedure was developed for in vitro synthesis of an immunogen, bovine serum albumen-glutathione-aflatoxin B1 (BSA-GSH-AFB1) using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride. Sulphydryl group's analysis confirmed the conjugation of SH groups to AFB1. Thin-layer chromatography and spectral analysis (absorption, fluorescence, and Fourier transform infrared) of the conjugates further confirmed the formation of the adducts. Polyclonal antibodies specific to mercapturic acid-AFB1 adduct were produced against BSA-GSH-AFB1. The assay was found to be linear in the range of 100 pg100 ng of the analyte (y ab x). A 50 displacement of BSA-GSH-AFB1 antibodies was achieved at an inhibitory concentration (IC50)of 11.9 ng GSH-AFB1 (r2 0.98) and 1.22 ng N-acetyl-L-cysteine (NAC)-AFB1 (r2 0.98). Spiking 5 g/mL of reference standard to the control rat urine showed a recovery of 98 2. The immunoassay was validated in a rodent model exposed to a single oral dose of 1 mg/kg body mass of pure AFB1. The excretion of NAC-AFB1 adduct was quantitated at the end of 24 h. The concentration of the NAC-AFB1 adduct excreted in urine as determined by the immunoassay was found to be in the range of 3.225.97 g/mg creatinine. The present method may find wide application as a biochemical tool in molecular epidemiological and intervention studies with respect to human exposure to dietary aflatoxins.


1963 ◽  
Vol 41 (1) ◽  
pp. 481-486 ◽  
Author(s):  
J. Zsolt ◽  
Gy. Schneider ◽  
B. Matkovics

The authors investigated the carotenoids of different maize varieties of white, yellow, and red-colored grains in different phases of ripening. The carotenoids extracted from the grains were separated into benzene-soluble (epiphasic) and benzene-insoluble (hypophasic) fractions, and the components of these fractions were quantitatively measured and separated. The cause of the characteristic color of the grains is the difference in concentration of zeaxanthin, the main component of the hypophasic fraction. The following other carotenoids were demonstrated also: β-carotene, β-carotene-monoepoxide, violaxanthin, β-cryptoxanthin, antheraxanthin, xanthophyll, xanthophyll-monoepoxide, α-carotene. We could best explain the origin of the different carotenoids in terms of Cholnoky's theory.


2012 ◽  
Vol 31 (10) ◽  
pp. 3865-3879 ◽  
Author(s):  
Gregory P. McGovern ◽  
Fernando Hung-Low ◽  
Jesse W. Tye ◽  
Christopher A. Bradley

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