3,5-Dichloro-2'-O-methylanziaic acid

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3,5-Dichloro-2'-O-methylanziaic acid
Category Others
Catalog number BBF-05315
CAS 64185-14-4
Molecular Weight 513.41
Molecular Formula C25H30Cl2O7

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Description

It is produced by the strain of Lecanora sulphurata.

Specification

Synonyms Benzoic acid, 3,5-dichloro-2,4-dihydroxy-6-pentyl-, 4-carboxy-3-methoxy-5-pentylphenyl ester; Sulphurellin
IUPAC Name 4-(3,5-dichloro-2,4-dihydroxy-6-pentylbenzoyl)oxy-2-methoxy-6-pentylbenzoic acid
Canonical SMILES CCCCCC1=C(C(=CC(=C1)OC(=O)C2=C(C(=C(C(=C2O)Cl)O)Cl)CCCCC)OC)C(=O)O
InChI InChI=1S/C25H30Cl2O7/c1-4-6-8-10-14-12-15(13-17(33-3)18(14)24(30)31)34-25(32)19-16(11-9-7-5-2)20(26)23(29)21(27)22(19)28/h12-13,28-29H,4-11H2,1-3H3,(H,30,31)
InChI Key IDRJMRKONACJDM-UHFFFAOYSA-N

Properties

Appearance Crystal
Boiling Point 635.0±55.0°C at 760 mmHg
Melting Point 154-155°C (dec.)
Density 1.3±0.1 g/cm3
Solubility Soluble in Benzene, Acetone

Reference Reading

1. Hydrogen Peroxide-Responsive Triggers Based on Borinic Acids: Molecular Insights into the Control of Oxidative Rearrangement
Blaise Gatin-Fraudet, Mathilde Pucher, Thomas Le Saux, Gilles Doisneau, Yann Bourdreux, Ludovic Jullien, Boris Vauzeilles, Dominique Guianvarc'h, Dominique Urban Chemistry. 2022 Oct 21;28(59):e202201543. doi: 10.1002/chem.202201543. Epub 2022 Aug 26.
Arylborinic acids represent new, efficient, and underexplored hydrogen peroxide-responsive triggers. In contrast to boronic acids, two concomitant oxidative rearrangements are involved in the complete oxidation of these species, which might represent a major limitation for an efficient effector (drug or fluorophore) release. Herein, a comprehensive study of H2 O2 -mediated unsymmetrical arylborinic acid oxidation to investigate the factors that could selectively guide their oxidative rearrangement is described. The o-CF3 substituent was found to be an excellent directing group allowing a complete regioselectivity on borinic acid models. This result was successfully applied to synthesizing new borinic acid-based fluorogenic probes, which exclusively release the fluorescent moiety upon H2 O2 treatment. These compounds maintained their superior kinetic properties compared to boronic acids, thus further enhancing the potential of arylborinic acids as valuable new H2 O2 -sensitive triggers.
2. The acid tolerance responses of the Salmonella strains isolated from beef processing plants
Yunge Liu, Yimin Zhang, Lixian Zhu, Lebao Niu, Xin Luo, Pengcheng Dong Food Microbiol. 2022 Jun;104:103977. doi: 10.1016/j.fm.2022.103977. Epub 2022 Jan 7.
The development of the stationary-phase, low-pH-inducible acid tolerance response (ATR) in the Salmonella contaminant of beef during the processing arises food safety concerns, because it may evoke bacterial coping mechanisms against bactericidal insults and alter gene expression that contribute to pathogen virulence. However, information on the development of the ATR and the stability (defined as the capacity to maintain the acquired acid tolerance after induction) in the Salmonella during the production and distribution of beef is limited. After adaptation overnight, ATRs in the 79 strains of Salmonella isolated from beef processing plants were investigated by comparing the log reduction in the 2-h acid challenge trials at pH 3.0. Six representative strains were selected to further estimate the effect of three factors in the incubation period on the development of the ATR, including adapted pH values (5.0, 5.4, 6.0, and 7.0), temperatures (10 °C and 37 °C), and the adaptation media (meat extract and brain heart infusion media). The stability of acid tolerance during the long-time chilled storage (4 °C for 13 days) was also observed on two strains of serotypes S. Derby and S. Meleagridis. All the strains isolated from beef processing plants exhibited an enhanced acid tolerance indicating the widespread existence of ATR. The results also revealed that strain variability was present in the development of ATR. Significant tolerance to lethal acidic environments (pH 3.0) was found when the Salmonella strains had been acid-adapted in meat extract at pH 5.0, pH 5.4, or pH 6.0, which indicated the possible induction of ATR during beef production. After the acid adaptations, the population reduction after the acid challenge (BHI, pH = 3) in the strains was significantly lower than the non-induced at the 1d, 7 day and 13 day's storage in meat extract media at 4 °C, which revealed the persistence of ATR during beef distribution. Compared to 37 °C, adaptation in lower temperature (10 °C) significantly reduced the ATR and no ATR was developed when adapted in 4 °C. This emphasizes the importance of keeping a low temperature of beef throughout the supply chains of beef industry.
3. Thermal properties and pyrolysis kinetics of phosphate-rock acid-insoluble residues
Rui Li, Weilong He, Jiangfei Duan, Shengxia Feng, Yu Zhang Waste Manag. 2022 Jun 1;146:77-85. doi: 10.1016/j.wasman.2022.04.039. Epub 2022 May 12.
In the phosphorous-sulphur two-step process for the clean production of phosphoric acid, a phosphate-rock acid-insoluble residue (PAIR) is a solid filter residue obtained via the phosphoric acid acidolysis of phosphate rock (PR). PAIR combined with other raw materials can be used to prepare cement, ceramics and glasses, opening a potential avenue for large-scale PAIR utilisation. However, the preparation of such materials requires high-temperatures calcination. Understanding the high-temperature thermal properties of PAIR can enable its more targeted comprehensive utilisation or disposal. In this study, the thermal properties and pyrolysis kinetics of PAIR were systematically studied using a multiple heating rate method based on thermogravimetric analysis and a kinetic model. Results showed that from room temperature to 1200 °C, the main changes in the PAIR were the complete removal of fluorine and sulphur, partial removal of phosphorus and conversion of quartz to cristobalite. Moreover, during these processes, H2O(g), NH3, N2, CO2, SO2, P2O5(g), CO, CF3+ and organic gases were volatilised. Herein, the pyrolysis kinetics of PAIR is divided into five stages. Stage 1 (conversion rate ɑ: 0.05-0.2) conforms to the random nucleation and growth as well as the Avrami-Erofeev (n = 2/3) mechanism; the corresponding mechanism function is F(ɑ) = [-Ln(1 - ɑ)]2/3. Stage 2 (ɑ: 0.2-0.4) conforms to the first-order chemical reaction mechanism; the corresponding mechanism function is F(ɑ) = -Ln(1 - ɑ). Stage 3 (ɑ: 0.4-0.6) conforms to the phase boundary-controlled reaction and one-dimensional movement mechanism; the corresponding mechanism function is F(ɑ) = ɑ. Stage 4 (ɑ: 0.6-0.8) conforms to the three-dimensional diffusion process (Jander model); the corresponding mechanism function is F(ɑ) = [1 - (1 - ɑ)1/3]2. Stage 5 (ɑ: 0.6-0.95) conforms to the one-dimensional diffusion process; the corresponding mechanism function is F(ɑ) = ɑ2.

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