• Title/Summary/Keyword: 4-Methyl benzoic acid

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Synthesis, Characterization and Antimicrobial Activity of Bifunctional Sulfonamide-Amide Derivatives

  • Abbavaram, Babul Reddy A.;Reddyvari, Hymavathi R.V.
    • Journal of the Korean Chemical Society
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    • v.57 no.6
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    • pp.731-737
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    • 2013
  • A convenient synthesis of bifunctional sulfonamide-amide derivatives was reported. Amide coupling of 4-methyl benzoic acid 1 followed by reaction with chlorosulfonic acid produce ethyl-4-(3-(chlorosulfonyl)-4-methylbenzoyl)piperazine-1-carboxylate 4. The resulted compound on further treatment with various anilines produces the title sulfonamide-amide derivatives 5a-n. The configurations of these compounds were established by elemental analysis, IR, $^1H$ NMR, mass spectra, and by their preparation from the corresponding 4-methyl benzoic acid 1 and chlorosulfonic acid. All these new compounds demonstrate significant in vitro antibacterial and antifungal activities against all bacterial and fungal strains.

Synthesis of N-acyl-α-aminosuccinimides and N-acyl-α-aminoglutarimides (N-아실-α-아미노숙신이미드와 N-아실-α-아미노글루탈이미드의 합성)

  • 정대일;김문주;송현애;김윤영;이용균;박유미;최순규;한정태;박민수
    • Journal of Life Science
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    • v.14 no.1
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    • pp.91-97
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    • 2004
  • As a part of our study on the improvement of anticonvulsant, here we report the synthesis of N-acyl-$\alpha$-aminosuc-cinimides 1 and N-acyl-$\alpha$-aminoglutarimides 2. (R)-Benzoic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-ylester 6a, (R)-4-nifro-benzoic acid 4-benzyloxycarbonylamino-2- oxo-pyrrolidin-1-yl ester 6b, (R) -4-nitro-benzoic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl ester 6c, and (R)-propionic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl ester 6d were synthesized from (R)-2-benzyloxy carbonylamino-succinic acid 3 as a starting meterial. (R)-(3- Benzyloxycarbonylamino-2,6-dioxo-piperidin-1-yloxy)-acetic acid methyl ester 10a, (R)-(3-benzyloxycarbonylamino-2,6-dioxo-piperidin-1-yloxy)-acetic acid ethy1 ester 10b, an d (R)-2-(3-benzyloxycarbonylamino-2,6- diox o-piperidin-1-yl oxy)-propionic acid methyl ester l0c were synthesized from (R)- 3-carbobenzyloxy-amino-glutarmic acid 7 as a starting meterial. The yield, mp, IR, $^1H-NMR,\; and^{13}C$- NMR spectra of the products 6a, 6b, 6c, 6d, 10a, l0b, l0c are summarized in footnote. The biological studies of these compounds are in progress and will be reported in future.

Growth of Pseudomonas aeruginosa in Cosmetics(Emulsion-type) and the Effect of Antiseptics (화장품(에멀젼형)에서 Pseudomonas aeruginosa의 성장과 방부살균제효과)

  • 류미숙;김장규김남기
    • KSBB Journal
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    • v.7 no.2
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    • pp.118-125
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    • 1992
  • Most of cosmetics are emulsion-type products which contain the sources of nutrition, i.e., vegetable oil, mineral oil and carbohyrate etc.. These additives are usually very susceptible to the contamination by microorganisms. The purpose of this study is to obtain the data necessary not only to prevent dermalopathia occurred by microbials but also to maintain the quality. In this experiment we observed the growth of P.aeruginosa in the cosmetics with or without antiseptics so as to prevent contamination. During the contamination period, the phase became unstable and creaming phenomina was happened together with some discoloration and bad smell. The pH of cosmetic was decreased from 7.6 to 6.0 and the concentration was increased from 1.443 to 1.453 in terms of refractive index during 40 days incubation. By adding antiseptics to the cosmetics, the number of P. aeruginosa from the challenge test method were decreased from $10^8$ cell/ml to $5{\times}10^3$ cell/ml. For the antibacterial effect against P. aeruginosa, p-hydroxy benzoic acid propyl ester in phosphoric acid buffer solution showed the best result.

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Studies on the effect of phthalimido methyl-O,O-dimethyl-phosphorodithioate (Imidan) and its possible metabolites on the growth of rice plant (Phthalimido methyl-O,O-dimethyl phosphorodithioate (Imidan)과 그의 대사물질(代謝物質)이 수도(水稻) 생육(生育)에 미치는 영향(影響)에 관(關)한 연구(硏究))

  • Lee, Sung-Hwan;Lee, Dong-Suk;Lee, Jae-Koo
    • Applied Biological Chemistry
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    • v.7
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    • pp.105-117
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    • 1966
  • This experiment was conducted to investigate the effet of phthalimido-methyl-O,O-dimethyl-phosphorodithioate (Imidan) known as an acaricide and its possible metabolic products on the growth of plant, when sprayed on the leaves of rice plant. The results are summarized as follows. 1) Possible metabolic products of Imidan, the following compounds were synthesized or recrystallized for the present experiment a) N-Hydroxymethyl phthalimidem b) Phthalimide c) Phthalamidic acid d) Phthalic acid e) Anthranilic acid f) p-Amino benzoic acid g) p-Hydroxy benzoic acid h) Benzoic acid 2) Among the above materials, a), c), d), e), and Imidan were dissolved in a buffer solution respectively to be 10 and 20 p.p.m. and tested with the wheat coleoptile straight growth method. According to the results, Imidan inhibited the growth of coleoptile in both 10 and 20 p.p.m., whereas the others showed much better growth than the control, especially phthalamidic acid in 10 p.p.m. It appears that Imidan itself inhibits the coleoptile growth, whereas the metabolites derived from Imidan through various metabolisms, including hydrolysis in plant tissues show growth-regulating activity. (refer: Table 1, Fig. 1) 3) 20, 100 and 200 p.p.m. solutions of Imidall emulsion in xylene f·ere prepared. The lengths of shoot and root of rice seeds germinated on the re-respective media were measured after 12 days. The data showed that root was much more elongated in Imidan 20 p.p.m., whereas shoot in Imidan 100 p.p.m., respectively, than in the xylene control. An interesting finding was that xylene used as solvent had a tendency to inhibit seriously the root growth of rice seed. (refer: Table 2,5). 4) The emulsions of concentrations in 10, 25, 50 and 100 p.p.m's of control, Imidan, N-hydroxy methyl phthalimide, anthranilic acid, and phthalmide, respectively, were sprayed twice on the rice plant on pot. After a certain period of time lengths of rice culms were measured, showing that plots treated with Imidan and N-hydroxy methyl phthalimide exhibited much more growth than those of control and the others. 5) Loaves and stems of rice plant were sampled and extracted with dried acetone at the intervals of 3-, 5-, 7-, and 14 days after treated with Imidan 250 p.p.m. emulsion. This sample extracted with acetone was purified by means of prechromatographic purification method with acetonitrile and paperchromatographed to detect the following metabolic products. Imidan (Rf: 0.97-0,98), N-hydroxy-methyl phthalimide (Rf: 0.87) phthalimide (Rf: 0.86-0.87), phthalamidic acid (Rf: 0.13-0.14), phthalic acid (Rf: 0.02-0.03), benzoic acid (Rf: 0.42-0.43), p-amino benzoic acid or p-hydroxy benzoic acid (Rf: 0.08-0.09), and unidentified compounds (Rf: 0.73, 0.59, 0.33, 0.23. 0.07). In addition, in the early stages, such as 3- and 5 days nonhydrolyzed Imidan and its first hydrolytic product, N-hydroxymethyl phthalimide were detected in relatively large amounts, whereas in the last stages of 7- and 14 days due to further decomposition, the afore-mentioned two materials were reduced in the amount and p-hthalic, phthalamidic, benzoic, and p-Hydroxy benzoic, or p-Amino benzoic acids were detected in a considerably large amount. It is, therefore, believed that most of Imidan applied to the leaves of rice plant may be decomposed within almost 14 days. In the light of above observations it is considered that Imidan itself is not involved in plant growth regulating activity, whereas various phthaloyl derivatives produced in the course of metabolism (namelr, enzymic action) in plant tissues may have such effect.

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Compositions of Fatty Acids, Inorganic Components and Volatile Organic Acids in Korean Valerian Roots (한국산 쥐오줌풀의 지방산, 무기성분 및 유기산 조성)

  • Choi, Young-Hyun;Cho, Chang-Hwan
    • Korean Journal of Medicinal Crop Science
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    • v.2 no.2
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    • pp.162-167
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    • 1994
  • This study was carried out to investigate the compositions of fatty acids, inorganic components and volatile organic acids from Korean valerian roots, Valeriana fauriei var. dasycarpa Hara and Valeriana officinalis var. latifolia Miq. The contents of total lipids ranged from 3.7 % to 4.5% and the major fatty acids were linoleic, linolenic and palmitic acid. Ash contents ranged from 4.3% to 6.3%. and the contents of Na, Fe, Zn and Cu showed some quantitative differences depending upon grown region or species. Fourty components were identified from acidic fraction of dichloromethane extract of V. fauriei var. dasycarpa Hara, of which the major components were 3-methyl butanoic, dimethoxy-2-propenoic. 3, 4-dimethoxy benzoic and 3-methyl pentanoic acid.

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Growth Characteristics and Ingredient Analysis According to the Transplanting Date and Distance of Dendranthema (L.). (감국 정식시기와 거리에 따른 생육특성과 성분 분석)

  • Jung, J.H.;Park, N.B.
    • Journal of Practical Agriculture & Fisheries Research
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    • v.22 no.1
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    • pp.65-77
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    • 2020
  • In order to industrialize of Dendranthema indicum (L.) DesMoul., which is a lot of commercially available and is synonymous with chrysanthemum tea, in the autumn of 2018, Dendranthema indicum (L.) DesMoul. seeds were collected from its own native region, and the seeds were germinated after refrigerated storage. Young seedlings were subjected to experiments in February, March, and April in the open field to examine the effects on the harvesting of leaves by distance and the growth of leaves and stems. The results of analyzing the components by collecting the leaves+stem after collecting the flower of Dendranthema indicum (L.) DesMoul. are as follows. 1. When D. indicum (L.) DesMoul. seedlings were planted according to the transplanting date, the number of flowers was 17.1 in the transplanting date in April. The diameter of the flower was 2.9cm, 16ea, 6.5~6.6g in the fresh weight, and the dry weight of the case was 1.1~1.2g. The leaves were 46~47ea in March and April in the planted area, 5.2~5.3cm in leaf length and 3.5~3.6cm in leaf width. 2. When planted D. indicum (L.) DesMoul. seedlings according to transplanting distance, the number of flowers was 16.2 when planted at 20×20cm intervals and, 16.8~17.1 at 30×30~50×50cm intervals. The diameter of the flower was 2.7~2.8cm, the number of petals was 8, the length of the petal was 0.8 cm, and fresh weight was 6.5~6.6g per flower. Leaves had the largest number of 47 of 30×30cm and 40×40cm, and leaf length appeared at the longest 6.2cm in the 50×50cm treatment area, but 5.2cm in the other treatment areas. 3. The extraction yield of D. indicum (L.) DesMoul. leaves+stems was 7.93%, and the extraction solvent colors were light green at 50, 60% and green at 70, 80, 90, 100%. The extraction yield of D. indicum (L.) DesMoul. flowers was 7.58%, the color of the extraction solvent was light yellow at 50, 60 and 70%, yellow at 80 and 90%, and dark yellow at 100%. 4. We confirmed 11 kinds of ingredients such as in D. indicum (L.) DesMoul. flowers are gallic acid, 4-hydroxy benzoic acid, methyl gallate, 4-hydroxy-3-methoxy benzoic, caffeic acid, salicylic acid, p-coumaric acid, sinapic acid, naringin, 4-melthoxyben, flavone. The content was 29.200-36.900ppm. 5. The components contained in the D. indicum (L.) DesMoul. leaf+stem, salicylic acid appeared at 6,129.526ppm, and the next 4-methoxyben was 1,966.714ppm. It was methyl gallate 8.197ppm, 4-hydroxy-3-methoxy benzoic 6.994ppm, caffeic acid 5.566ppm, flavone 4.522ppm, p-coumaric acid 3.787ppm, gallic acid 1.893ppm that appeared in the content below 10ppm.

An analysis of benzoic acid, methyl paraben and butyl paraben in soy sauce using isotope dilution liquid chromatography mass spectrometry (동위원소희석 질량분석법을 이용한 간장 중의 안식향산, 메틸파라벤, 부틸파라벤의 분석)

  • Ahn, Seonghee
    • Analytical Science and Technology
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    • v.31 no.6
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    • pp.225-231
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    • 2018
  • Benzoic acid, methyl paraben, and butyl paraben are preservatives that have been used in pharmaceutical, cosmetic, and food products. However, as their toxicities for human have been reported, many nations and organizations including Korea have established a regulation limit for thier usage of these preservatives in food products. The present study developed the isotope dilution liquid chromatography mass spectrometry method for accurate determination of three target preseratives in soysauce. In this study, the isotope dilution liquid chromatography mass spectrometry method was developed for accurate determination of three target preservatives in soy sauce. LC separation was optimized considering the pKa of benzoic acid which is lower than those of methyl and butyl parabens. A C18 column was used with 5 mM ammonium acetate and methanol as mobile phases. Mass spectrometry was operated in negative mode and selected reaction monitoring mode (SRM). Soy sauce sample was cleaned-up with C18 SPE cartridge for removing matrix inferences and color material. Optimized conditions and the method were validated with soy sauce reference materials for the analysis of food preservatives from Health Science Authority in Singapore. The measured values of benzoic acid, methyl and butyl paraben agreed well with reference values within their uncertainties.

Extractives from the Needles of Torreya (벼자나무 잎의 추출성분)

  • Kim, Jin-Kyu;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.29 no.4
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    • pp.53-59
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    • 2001
  • The needles of torreya(Torreya nucifera S. et Z) were collected, extracted with acetone-$H_2O$(7:3, v/v), fractionated with hexane, chloroform and ethylacetate, and freeze dried to give some dark brown powder. The ethylacetate soluble mixture was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents. Most of the needle extractives were flavan and its methyl ether compounds such as (+)-catechin, (-)-epicatechin, (+)-gallocatechin, (-)-epigallocatechin, 3'-O-methyl-(+)-catechin and 3'-O-methyl-(-)-epicatechin including protocatechuic acid, one of benzoic acids. $^1H$- and $^{13}C$-NMR, NOE and CI-MS analyses were performed to elucidate the structures of the isolated compounds.

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Synthesis and Biological Activity of Fungal Metabolite, 4-Hydroxy-3-(3'-Methyl-2'-Butenyl)-Benzoic Acid

  • Kim, Hye-Jin;Kwon, Ho-Jeong
    • Journal of Microbiology and Biotechnology
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    • v.17 no.3
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    • pp.543-545
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    • 2007
  • 4-Hydroxy-3-(3'-methyl-2'-butenyl)-benzoic acid (HMBA) was previously isolated from Curvularia sp. KF119 as a cell-cycle inhibitor. However, the present study used a novel and practical synthetic method to prepare a large quantity of HMBA. The synthetic HMBA was found to inhibit the cell-cycle progression of HeLa cells with a comparable potency to the natural fungal metabolite. The inhibition of the cell-cycle progression by the synthetic HMBA involved both the activation of $p21^{WAF1}$ and the inhibition of cyclin D1 expression in the cells. Consequently, this new synthetic procedure provides an easy and convenient way to produce or manipulate the original fungal metabolite.