Category: 1139-46-4

Rajendran, Ranjith kumar published the artcileBiodegradation of the endocrine disrupter 4-tert-octylphenol by the yeast strain Candida rugopelliculosa RRKY5 via phenolic ring hydroxylation and alkyl chain oxidation pathways, Related Products of alcohols-buliding-blocks, the publication is Bioresource Technology (2017), 55-64, database is CAplus and MEDLINE.

4-(1,1,3,3-Tetramethylbutane)-phenol (4-tert-OP) is one of the most prevalent endocrine disrupting pollutants. Information about bioremediation of 4-tert-OP remains limited, and no study has been reported on the mechanism of 4-tert-OP degradation by yeasts. The yeast Candida rugopelliculosa RRKY5 was proved to be able to utilize 4-methylphenol, bisphenol A, 4-ethylphenol, 4-tert-butylphenol, 4-tert-OP, 4-tert-nonylphenol, isooctane, and phenol under aerobic conditions. The optimum conditions for 4-tert-OP degradation were 30°C, pH 5.0, and an initial 4-tert-OP concentration of 30 mg L^-1; the maximum biodegradation rate constant was 0.107 d^-1, equivalent to a min. half-life of 9.6 d. SEM revealed formation of arthroconidia when cells were grown in the presence of 4-tert-OP, whereas the cells remained in the budding form without 4-tert-OP. Identification of the 4-tert-OP degradation metabolites using liquid chromatog.-hybrid mass spectrometry revealed three different mechanisms via both branched alkyl side chain and aromatic ring cleavage pathways.

Bioresource Technology published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Pedersen, R. T. published the artcileIdentification of novel metabolites of the xenoestrogen 4-tert-octylphenol in primary rat hepatocytes, COA of Formula: C14H22O2, the publication is Chemico-Biological Interactions (2000), 128(3), 189-209, database is CAplus and MEDLINE.

A number of environmental pollutants, including 4-tert-alkylphenols, can mimic the actions of endogenous steroids and have the potential to disrupt the endocrine function in humans and animals. The biotransformation of a 4-tert-alkylphenol in isolated rat hepatocytes was studied in order to determine the possible fate and activity of these xenoestrogens in higher vertebrates. Hepatocytes were incubated with 30 μM 4-(1′,1′,3′,3′-tetramethylbutyl)[U-¹⁴C]phenol (4-tert-octylphenol; t-OP) for up to 60 min. Radiolabeled metabolites were detected by radio-HPLC and the structures determined by gas chromatog.-mass spectrometry (GC-MS) anal. of the conjugated or aglycon products. After a 15 min incubation, over 97% of t-OP was metabolized to a complex mixture of metabolites. The initial metabolites formed were identified as products of hydroxylation of the aromatic ring to form catechols and methylated catechols, as well as glucuronide conjugates of the catechol metabolites or parent phenol. These products were further metabolized by hydroxylation of the alkyl chain followed by glucuronide conjugation of the alkoxy group. The conjugated metabolites of t-OP are unlikely to retain estrogen receptor activity; however t-OP is metabolized by some pathways that are similar to that of estrogen catabolism, namely by ortho-hydroxylation to form catechols, methylation by catechol O-methyltransferases and ring conjugation by uridine diphosphoglucuronosyl transferases. Further investigations are needed to determine whether 4-tert-alkylphenols can alter circulating sex steroid profiles by acting as substrates of enzymes determining estrogen metabolism and excretion.

Chemico-Biological Interactions published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, COA of Formula: C14H22O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Lin, Yi-Wen published the artcileGrowth of Pseudomonas sp. TX1 on a wide range of octylphenol polyethoxylate concentrations and the formation of dicarboxylated metabolites, Related Products of alcohols-buliding-blocks, the publication is Bioresource Technology (2010), 101(8), 2853-2859, database is CAplus and MEDLINE.

Pseudomonas sp. TX1, is able to use octylphenol polyethoxylates (OPEO_n, or Triton X-100; average n = 9.5) as a sole carbon source. It can grow on 0.05-20% of OPEO_n with a specific growth rate of 0.34-0.44 h^-1. High-performance liquid chromatog.-mass spectrometer anal. of OPEO_n degraded metabolites revealed that strain TX1 was able to shorten the ethoxylate chain and produce octylphenol (OP). Furthermore, formation of the short carboxylate metabolites, such as carboxyoctylphenol polyethoxylates (COPEO_n, n = 2, 3) and carboxyoctylphenol polyethoxycarboxylates (COPEC_n, n = 2, 3) began at the log stage, while octylphenol polyethoxycarboxylates (OPEC_n, n = 1-3) was formed at the stationary phase. All the short-ethoxylated metabolites, OPEO_n, OPEC_n, COPEO_n, and COPEC_n, accumulated when the cells were in the stationary phase. This study is the first to demonstrate the formation of COPEO_n and COPEC_n from OPEO_n by an aerobic bacterium.

Bioresource Technology published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Horner, Leopold published the artcileo-Quinones. XXVII. Redox potentials of pyrocatechol derivatives, Recommanded Product: 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, the publication is Chemische Berichte (1965), 98(6), 2016-45, database is CAplus.

cf. Ibid. 2009-15; CA 62, 16155a. The polarographically determined standard redox potentials of 121 pyrocatechol derivatives, among them 28 substituted 1′,2′-dihydroxy-6,7-benzotropolones, were reported. The substituent effect on increments corresponding to the redox potential is approx. additive for many substituents. The redox potentials are discussed.

Chemische Berichte published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, Recommanded Product: 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Pospisil, Jan published the artcileOxidation of catechol. IV. Oxidation of 4-tert-octylcatechol, HPLC of Formula: 1139-46-4, the publication is Chemicke Listy pro Vedu a Prumysl (1958), 939-47, database is CAplus.

cf. C.A. 52, 4546g. Oxidation of 4-tert-octylcatechol (I) (tert-octyl = R = Me₃CCH₂CMe₂) with O or alk. H₂O₂ gave 2-hydroxy-5-tert-octyl-1,4-benzoquinone (II), also obtained by oxidation of 4-tert-octyl-1,2-benzoquinone (III). The oxidation of I is assumed to proceed through intermediate 1,2,4-trihydroxy-5-tert-octylbenzene (IV) to II. A similar mechanism is proposed for the oxidation of catechol (V) to 2,5-dihydroxy-1,4-benzoquinone (VI). Alkylation of pyrogallol (VII) with di-isobutylene (VIII) gave 5-tert-octylpyrogallol (IX) whose oxidation with Ag₂O yielded 6-hydroxy-4-tert-octyl-1,2-benzoquinone (X). Dissolving 110 g. resublimed V in 448 g. hot VIII, treating the solution with 0.2 ml. concentrated H₂SO₄, stirring the mixture 2.5 hrs. at 105-15°, cooling, filtering off the product with suction, and washing with H₂O yielded 167.6 g. I, m. 108° (ligroine). Adding a solution of 4.5 g. I in 220 ml. Et₂O to a mixture of 100 ml. Et₂O, 5 g. anhydrous Na₂SO₄, and Ag₂O prepared from 135 g. AgNO₃, shaking 5 min., filtering, and evaporating gave 4.29 g. III, m. 121-1.5° (Et₂O). Acetylation of 2.2 g. I by heating with 6 ml. Ac₂O and 0.1 ml. concentrated H₂SO₄ 20 min. on the steam-bath gave 1.8 g. 1,2-diacetoxy-4-tert-octylbenzene, m. 49.5°. The same compound was also obtained by boiling for 10 min. a mixture of 0.44 g. III, 1 g. anhydrous NaOAc, 1.0 g. Zn dust, and 12 ml. Ac₂O. To oxidize I, O was passed into a solution of 68 g. KOH in 300 ml. 75% MeOH at a rate of 0.2-0.3 l./min. at 30°. After 15 min., 10 g. I in 100 ml. 75% MeOH was added over a period of 2.5 hrs. The initial blue color turned red. The red clear solution was diluted with 300 ml. H₂O, 300 g. ice was added, and the mixture acidified with concentrated HCl. The solution turned yellow and a yellow product precipitated Evaporation of the MeOH in vacuo yielded another crop of II, m. 133.5-4.5° (decomposition) (petr. ether) (7.45 g., 70.1% total). Dissolving 4.5 g. I in 50 ml. 5% solution of KOH in 50% MeOH, treating this solution at 40° with 7 ml. 40% H₂O₂ for 30 min., stirring the mixture 1.5 hrs., decanting the red solution from resinous material, diluting it to a 10-fold volume with ice and H₂O, and acidifying with HCl gave 69.8% II. The same compound was obtained also by oxidation of 0.22 g. III in methanolic solution of KOH (containing 4.5 g. KOH in 45 ml. 75% MeOH) by passing 0.15-0.2 l./min. O through the solution 1.5 hrs. (yield 41.3%) or by treating 0.5 g. III in 2.2 ml. MeOH with 2.5 ml. 40% aqueous KOH and 1.4 ml. 40% H₂O₂ 1 hr. at 40° (yield 15.3%, 0.08 g.). Absorption of II in 0.1N aqueous KOH showed log ε 4.086 at 285 mμ, and log ε 3.216 at 495 mμ. Heating 1 g. II with 5 ml. Ac₂O and 0.1 ml. concentrated H₂SO₄ 2 hrs. at 45° and diluting the mixture after 20 hrs. with 20 ml. H₂O yielded 0.95 g. 2-acetoxy-5-tert-octyl-1,4-benzoquinone (XI), m. 89.5-90° (petr. ether). Dissolving 0.2 g. XI in 5 ml. Ac₂O, adding 0.5 g. Zn dust and 0.5 g. anhydrous NaOAc, refluxing the mixture 30 min., filtering off the Zn, and diluting the filtrate with 25 ml. H₂O and 25 g. ice gave 0.22 g. triacetate (XII) of IV, m. 88.5° (petr. ether). The same compound was obtained by treating similarly 2 g. II in 25 ml. Ac₂O with 2.5 g. Zn dust and 2.5 g. NaOAc; yield 2.62 g. Hydrogenation of 0.11 g. II in 20 ml. glacial AcOH and 40 ml. Ac₂O over PtO₂ and heating the mixture with 0.2 ml. concentrated H₂SO₄ 20 min. under H gave XII. If the hydrogenation was carried out in MeOH, the colorless solution of IV formed was reoxidized in contact with air. Heating 30 g. VII with 172 g. VIII and 0.1 ml. concentrated H₂SO₄ 3 hrs. at 105-15° gave 30.7 g. (51.7%) IX, m. 104° (ligroine). Shaking 1.2 g. IX in 100 ml. Et₂O with 12 g. Ag₂O and 10 g. anhydrous Na₂SO₄ in 50 ml. Et₂O for 10 min. gave a red solution of X whose reductive acetylation by heating with 5 ml. Ac₂O, 0.5 g. NaOAc, and 0.5 g. Zn dust in 30 ml. C₆H₆ gave 1,2,3-triacetoxy-5-tert-octylbenzene, m. 71° (petr. ether). The same compound was also obtained by allowing 0.37 g. III to stand 24 hrs. at 20° with 10 ml. Ac₂O and 0.1 ml. H₂SO₄ or by heating 1 g. IX with 8 ml. Ac₂O and 0.1 ml. H₂SO₄ 10 min. on the steam bath (yield 1.25 g.). Heating 0.28 g. VI, 6 ml. Ac₂O, and 0.1 ml. H₂SO₄ 2 hrs. at 50° and diluting the mixture after 20 hrs. with ice and H₂O gave 0.27 g. 2,5-diacetoxy-1,4-benzoquinone (XIII), m. 151-2° (decomposition) (AcOH). Hydrogenation of 0.14 g. VI in 40 ml. MeOH over PtO₂ at 18° gave impure 1,2,4,5-tetrahydroxybenzene whose acetylation with 5 ml. Ac₂O and 1 drop H₂SO₄ gave tetraacetate, m. 226° (AcOH).

Chemicke Listy pro Vedu a Prumysl published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, HPLC of Formula: 1139-46-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Saxena, A. K. published the artcileModelling the binding affinity of steroids to zebrafish sex hormone-binding globulin, Synthetic Route of 1139-46-4, the publication is SAR and QSAR in Environmental Research (2014), 25(5), 407-421, database is CAplus and MEDLINE.

The circulating endogenous steroids are transported in the bloodstream. These are bound to a highly specific sex hormone-binding globulin (SHBG) and in lower affinity to proteins such as the corticosteroid-binding protein and albumin in vertebrates, including fish. It is generally believed that the glycoprotein SHBG protects these steroids from rapid metabolic degradation and thus intervenes in its availability at the target tissues. Endocrine disrupters binding to SHBG affect the normal activity of natural steroids. Since xenobiotics are primarily released in the aquatic environment, there is a need to evaluate the binding affinity of xenosteroid mimics on fish SHBG, especially in zebrafish (Danio rerio), a small freshwater fish originating in India and widely employed in ecotoxicol., toxicol., and genetics. In this context, a zebrafish SHBG (zfSHBG) homol. model was developed using the human SHBG (hSHBG) receptor structure as template. It was shown that interactions with amino acids Ser-36, Asp-59 and Thr-54 were important for binding affinity. A ligand-based pharmacophore model was also developed for both zfSHBG and hSHBG inhibitors that differentiated binders from non-binders, but also demonstrated structural requirements for zfSHBG and hSHBG ligands. The study provides insights into the mechanism of action of endocrine disruptors in zebrafish as well as providing a useful tool for identifying anthropogenic compounds inhibiting zfSHBG.

SAR and QSAR in Environmental Research published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, Synthetic Route of 1139-46-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Nomura, Sachiko published the artcileDifferential metabolism of 4-n- and 4-tert-octylphenols in perfused rat liver, Formula: C14H22O2, the publication is Life Sciences (2008), 83(5-6), 223-228, database is CAplus and MEDLINE.

Octylphenols, widely used in a variety of detergents and plastics, are known to exhibit estrogenicity in vivo. The details of their metabolism are needed to better understand the endocrine disruptions. We have previously shown that alkylphenols, having short alkyl chains, are glucuronidated and readily excreted into the bile from the liver, while 4-n-nonylphenol, having longer alkyl chains, remains as the alkylphenol’s glucuronide in the tissue. This study elucidated the dependence of the metabolism on the shape of the alkyl chains by comparing 4-n-octylphenol and 4-tert-octylphenols in a perfused rat liver. Both octylphenols were highly glucuronidated by the liver microsomal fractions. The Vmax value of 4-tert-octylphenol glucuronidation was twice as high as that of 4-n-octylphenol in the liver microsomes. On the other hand, the Km values, being measures of enzymic activity against these chems., were similar. 4-n-Octylphenol and 4-tert-octylphenol were both glucuronidated by a UDP-glucuronosyltransferase isoform, UGT2B1, expressed in the liver. In the liver perfusion, almost all of the 4-n-octylphenol perfused was metabolized directly to the glucuronide, whereas a portion of 4-tert-octylphenol was hydroxylated and then glucuronidated. The glucuronide of 4-n-octylphenol accumulated in the liver tissue in the same manner as 4-n-nonylphenol, but 4-tert-octylphenol and the hydroxylated metabolites were excreted readily into the bile. Only a small amount of 4-n-octylphenol-glucuronide and glucuronides of 4-tert-octylphenol and its hydroxylated metabolites could be excreted into the bile of Eisai hyperbilirubinemic rats (EHBR). These animals are deficient in xenobiotic conjugate transporter, multidrug resistance-associated protein (MRP-2), indicating that the glucuronides of both octylphenols are transported by MRP-2. These results indicate that the differences in metabolism of these octylphenols are due to the shape of their alkyl chains, suggesting that the estrogenic activities of not only the parent chems. but also these metabolites must be taken into consideration.

Life Sciences published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, Formula: C14H22O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Barr, Rita published the artcileCatechols stimulate ferricyanide reduction in chloroplast photosystem II, Related Products of alcohols-buliding-blocks, the publication is Biochimica et Biophysica Acta, Bioenergetics (1979), 546(1), 77-83, database is CAplus and MEDLINE.

In isolated chloroplasts from Spinacia oleracea, where electron transport to photosystem I was blocked by the plastoquinone antagonist, dibromothymoquinone, lipophilic catechols in concentrations of 50-150 μM stimulated ferricyanide reduction in photosystem II and associated O evolution. Nonpermeating catechols, such as Tiron, were unable to stimulate this reaction. Those quinones, such as 2,5-dimethylbenzoquinone, which act as class III electron acceptors, did not stimulate ferricyanide reduction in photosystem II or associated O evolution when electron transport to photosystem I was blocked by dibromoquinone. Stimulation of ferricyanide reduction was not observed in Tris-treated chloroplasts, implying that electron donation to photosystem II by catechols is not responsible for the stimulation. Various mechanisms for this stimulation in class II chloroplasts are discussed.

Biochimica et Biophysica Acta, Bioenergetics published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Urban, Frank J. published the artcileLipophilic 1,3-xylyl-21-crown-6 macrocyclic polyether 2-carboxylic acids as biological mimics of the ionophore antibiotics, Product Details of C14H22O2, the publication is Journal of Medicinal Chemistry (1990), 33(2), 765-71, database is CAplus and MEDLINE.

Twelve lipophilic 1,3-xylyl-21-crown-6 macrocyclic polyether 2-carboxylic acids, e.g. I (R = H, Me, PhCH₂; n = 1), two lariat ether 1,3-xylyl-21-crown-6 macrocyclic polyether 2-carboxylic acids II (R¹ = H, Me₃C) and two 1,3-xyly-28-crown-8 macrocyclic polyether 2-carboxylic acids I (R = H, Me, n = 2) were synthesized and tested for in vitro antibacterial activity, in vitro stimulation of rumen propionic acid production, and in vivo anticoccidial activity in chickens. These are biol. screens relevant to animal health areas where the ionophore antibiotics such as monensin have found application. While the parent structure without lipophilic substituents was biol. inactive, the lipophilic macrocycles were active in the two in vitro tests but not against chicken coccidiosis. One compound I (R = Me, n = 1) was tested in cattle and was found to increase levels of propionic acid in the rumen fermentation This effect is considered an important factor for increasing the efficiency of feed utilization in cattle exhibited by the ionophore antibiotic monensin. The alkali ion salts of these lipophilic macrocyclic polyether carboxylic acids are very soluble in organic solvents and insoluble in water. These compounds are proposed to act as ion-transport agents and functional mimics of the ionophore antibiotics in the biol. systems described above.

Journal of Medicinal Chemistry published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C9H8FNO2, Product Details of C14H22O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Larson, Nicholas R. published the artcileToxicology of potassium channel-directed compounds in mosquitoes, Category: alcohols-buliding-blocks, the publication is NeuroToxicology (2017), 214-223, database is CAplus and MEDLINE.

Potential targets for new vector control insecticides are nerve and muscle potassium channels. In this study, the activities of known potassium channel blockers (4-aminopyridine, quinidine, and tetraethylammonium) and the insecticide propoxur were compared to three exptl. catechols and several other compounds against Anopheles gambiae and Aedes aegypti mosquitoes. Exptl. catechol 1 was the most toxic exptl. compound in all of the mortality assays conducted, but was at least 100-fold and 39-fold less toxic than propoxur against Ae. aegypti and An. gambiae, resp. Injection treatment and synergist (piperonyl butoxide) bioassays found that catechol toxicity was not unduly impacted by cuticular transport or oxidative metabolism Electrophysiol. studies showed a decrease in amplitude of evoked muscle contractions, along with an increase in twitch duration at concentrations that increased basal muscle tension (mM). High concentration effects on basal muscle tension were matched by complete depolarization of the muscle membrane potential. Effects on muscle physiol. and blockage of Kv2.1 potassium channels in patch clamp experiments were generally consistent with in vivo toxicity, except for 4-aminopyridine, which suggest the involvement of other potassium channel subtypes. Extensive melanization of Anopheles larvae, but not Aedes larvae, occurred from exposure to catechol compounds Interaction with the phenol oxidase system within insects may be the cause of this melanization, but any contribution to toxicity requires further investigation.

NeuroToxicology published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts