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[ CAS No. 1135-24-6 ] {[proInfo.proName]}

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Chemical Structure| 1135-24-6
Chemical Structure| 1135-24-6
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Krystian Klimczak ; Monika Cioch-Skoneczny ; Aleksander Poreda DOI:

Abstract: Among many methods to produce low/no-alcohol beers, using special yeasts has gained a substantial interest in the brewing industry. This approach relies on the fact that many non-Saccharomyces yeasts do not utilize maltose, which is the main sugar found in brewer’s wort. Additionally, these yeasts may allow the production of a beer with unique sensory characteristics. The aim of the study was to evaluate the potential of 18 non-Saccharomyces yeast strains in the production of low-alcohol beer. As a control strain, S. cerevisiae US-05 was used. The study consisted of two parts: microbiological evaluation and small-scale fermentations. In the microbiological part, ability to ferment sugars found in a wort, resistance to stress factors, phenolic off-flavor production, and enzymatic activities of β-glucosidase and β-lyase were evaluated. In the second part of the study, yeasts were used to produce a beer from 9.3 °Plato wort. During the fermentation, its dynamics was analyzed. The obtained beers were analyzed regarding their alcohol content, pH, acidity, and color. All of the evaluated strains produced low levels of alcohol. Two of the evaluated strains were characterized by especially high β-glucosidase activity. Based on the obtained results, six of the evaluated strains are promising in brewing.

Keywords: beer ; non-Saccharomyces ; low-alcohol beer

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Scott, Jared Lee ; DOI:

Abstract: Breast cancer (BC) is the second greatest contributor to the death of women, second only to heart disease, and is the most common type of cancer. BC treatments involve the administration of adjuvant chemotherapies which often have side effects that prevent patients from completing the full course of drugs or the refusal to take these potentially lifesaving treatments. Many chemotherapy drugs are developed from plants, and some plant extracts can exhibit significant anticancer activities while also having less toxic side effects. However, these potential "plant therapeutics" suffer from poor oral bioavailability. The Apiaceae plant family consists of several species that are used as culinarily spices including anise, celery, cumin, and coriander, all of which have demonstrated antioxidant, chemopreventive, and anticancer activities. One method to improve the systemic distribution of anticancer phytochemicals is their encapsulation in naturally produced membrane bound nanoparticles known as exosomes. Exosomes are produced by most eukaryotic organisms, as well as some prokaryotes, and are involved in cell-to-cell communication through the delivery of proteins, nucleic acids, and small molecules from one cell to another. Exosomes are found in many extracellular fluids including blood, urine, and milk. Bovine milk exosomes represent a scalable source of exosomes that are already present in the human diet and have been explored as a drug delivery system that can increase effectiveness and improve bioavailability. To enhance the loading potential and anticancer bioactivity of Apiaceae phytochemicals, an acid hydrolysis (AH) of the glycoside compounds present in ethanolic spice extracts was performed on eight ethanolic spice extracts. The antiproliferative effects of AH extracts and exosomal formulations were assayed with three model types of BC cells. Cumin was characterized in greater detail as these extracts had the highest concentration of terpenoids and alkaloids while also having significant concentrations of phenolics and responded well to AH with increased antiproliferative activity and exosomal loading. Extracts and exosomal formulations exhibited broad antiproliferative effects with lower IC50s in the extracts delivered with exosomes. The phytochemical contents of AH-cumin extracts and exosomal formulations were assayed with HPLC-DAD, LC-MS/MS, and GC-MS, while the potential anticancer mechanisms of these treatments were investigated in triple negative BC (TNBC). AHcumin extracts were determined to have numerous phenolic compounds, many of which have known anticancer mechanisms, in addition to several alkaloids and lipid compounds, some of which have activities that could contribute to the anticancer effects observed. Mechanistically, AH-cumin extracts and exosomal formulations were shown to interact with multidrug resistance proteins and inhibit lipid metabolism in TNBC cells. These results indicate that acid hydrolyzed cumin extracts delivered through exosome nanoparticles represent a possible avenue towards the development of novel treatments for TNBC, the hardest type of BC to treat.

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Janus, Ewa ; Pinheiro, Luan Ramalho ; Nowak, Anna , et al. DOI: PubMed ID:

Abstract: Ferulic acid (FA) has been widely used in the pharmaceutical and cosmetics industry due to its, inter alia, antioxidant, antiaging and anti-inflammatory effects This compound added to cosmetic preparations can protect skin because of its photoprotective activity. However, the usefulness of FA as a therapeutic agent is limited due to its low solubility and bioavailability. The paper presents the synthesis, identification, and physicochemical properties of new FA derivatives with propyl esters of three amino acids, glycine (GPr[FA]), L-leucine (LPr[FA]), and L-proline (PPr[FA]). The NMR and FTIR spectroscopy, DSC, and TG analysis were used as analytical methods. Moreover, water solubility of the new conjugates was compared with the parent acid. Both ferulic acid and its conjugates were introduced into hydrogel and emulsion, and the resulting formulations were evaluated for stability. Additionally, in vitro penetration of all studied compounds from both formulations and for comparative purposes using Franz diffusion cells was evaluated from the solution in 70% (v/v) ethanol. Finally, cytotoxicity against murine fibroblasts L929 was tested. All of the analyzed compounds permeated pig skin and accumulated in it. LPr[FA] and PPr[FA] were characterized by much better permeability compared to the parent ferulic acid. Additionally, it was shown that all the analyzed derivatives are characterized by high antioxidant activity and lack of cytotoxicity. Therefore, they can be considered as an interesting alternative to be applied in dermatologic and cosmetic preparations.

Keywords: antioxidant activity ; antiaging ; ferulic acid ; new ferulic acid and amino acid derivatives ; skin permeation ; toxicity ; vehicles containing new ferulic acid and amino acid derivatives

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Product Details of [ 1135-24-6 ]

CAS No. :1135-24-6 MDL No. :MFCD00004400
Formula : C10H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :KSEBMYQBYZTDHS-HWKANZROSA-N
M.W : 194.18 Pubchem ID :445858
Synonyms :
Coniferic acid;4-hydroxy-3-Methoxycinnamic Acid;Ferulic Acid, Methyl ferulate, trans-Ferulic acid, Coniferic acid, NSC 2821, NSC2821, NSC-2821;NSC 674320;NSC 51986;NSC 2821;Fumalic Acid
Chemical Name :3-(4-Hydroxy-3-methoxyphenyl)acrylic acid

Safety of [ 1135-24-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1135-24-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1135-24-6 ]

[ 1135-24-6 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 1135-24-6 ]
  • [ 2305-13-7 ]
  • 2
  • [ 1135-24-6 ]
  • [ 2305-13-7 ]
  • 3
  • [ 1135-24-6 ]
  • [ 500287-72-9 ]
  • 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile ferulate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.3 g With acetic acid; at 90 - 95℃; for 0.166667h;Inert atmosphere; EXAMPLE 10Preparation of <strong>[500287-72-9]Rilpivirine</strong> ferulate salt.A round bottom flask fitted with a mechanical stirrer, thermometer socket, addition funnel was purged with N2. The flask was charged <strong>[500287-72-9]rilpivirine</strong> free base, obtained fromExample 4 (1 gin) and acetic acid (5.5 ml). The reaction temperature was raised to 90C to 95C and ferulic acid (0.61 gms) was added at same temperature. The reaction mixture was stirred for 10 minutes and water (5.5 ml) was added at temperature 65C to 70C. The reaction mixture was allowed to cool to 25C to 35C and stirred for 1 hour. Precipitated solid was filtered and washed with water (2 ml). The wet product was driedat about 60C to about 65C under reduced pressure to provide the title compound. Yield: 1.3 gms.HPLC Purity: 98.95%Z-isomer: 0.54%
  • 5
  • [ 1135-24-6 ]
  • [ 14769-73-4 ]
  • levamisole ferulate [ No CAS ]
  • 6
  • [ 1135-24-6 ]
  • [ 4089-07-0 ]
  • [ 1597451-74-5 ]
  • 7
  • [ 1135-24-6 ]
  • [ 458-36-6 ]
  • [ 2305-13-7 ]
YieldReaction ConditionsOperation in experiment
22% With D-glucose; In aq. phosphate buffer; at 30℃; for 16h;pH 8.0;Enzymatic reaction; General procedure: Glucose (22.2 mM), E. coli BL21(DE3)/pETDuet-1-PPTase-CAR (wet cells, 10 g), and the substrate (20a, 5.0 mM) were mixed in the sodium phosphate buffer (100 mL, 100 mM, pH 8). The resulting mixture was incubated at 200 rpm in a rotary shaker at 30°C, and the reaction was monitored by GC. After 29 h, the pH of the reaction mixture was adjusted to 2?3 with 2 M HCl and the mixture was filtered through a Celite pad to remove the biomass. The resulting aqueous solution was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was puriedby a silica gel column to give the product.
  • 8
  • [ 887581-09-1 ]
  • [ 1135-24-6 ]
  • [ 119072-55-8 ]
  • [ 64904-47-8 ]
  • 2-{(2-bromo-5-methoxybenzyl)[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]amino}-3-(tert-butylamino)-3-oxopropyl benzoate [ No CAS ]
  • 9
  • [ 1135-24-6 ]
  • [ 2305-13-7 ]
  • (E)-3-(4-hydroxy-3-methoxyphenyl)propyl 3-(4-hydroxy-3-methoxyphenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 48h; General procedure: Triphenylphosphine (TPP) (280 mg, 1.07 mmol) was added in portions to a freshly prepared solution of the designated alcohol (1.0 mmol) and the specified phenolic acid (1.0 mmol equivalent) in anhydrous THF (3.5 mL) at 0 °C. Diisopropylazodicarboxylate (DIAD) (208 mL, 1.0 mmol) was then added dropwise to the mixture. The reaction mixture was stirred at 0 °C for 30 min. The mixture was then warmed and stirring was continued for 48 h at rt [19]. Reactions were monitored till completion by TLC. The reaction mixture was then worked up by removal of the solvent under reduced pressure, saturated solution of NaHCO3 (10 mL) was added, and then the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated under reduced pressure to dryness. The crude product was collected and purified by column chromatography(CC) on Sephadex LH-20 using isocratic CH2Cl2 followed by chromatography on Si gel 60 using n-hexane-EtOAc system, gradient elution, to afford 5-9 and 13-47 (Supplementary Information).
  • 10
  • [ 1135-24-6 ]
  • [ 1421-65-4 ]
  • N-[4′-hydroxy-3′-methoxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; General procedure: As shown in Scheme 1, the synthetic route of the analogues (1-7) involved a two-step sequence viamethyl esterification of L-amino acidand amide condensation. 100 muL SOCl2was added in portions to 4 mL methanol at -10 C,then 1 mmol L-amino acid was addedand the mixture was warmed to room temperature and stirred overnight. After thesolvent was removed, 5 mL CH3CN, 500 muL DIPEA (N,N-Diisopropyl ethylamine), 1.1 mmolcorresponding substituted acid and 1.1 mmol HBTU (O-Benzotriazole-N,N,N',N'-tetramethyl-uronium-hexafluorophosphate)was added into the residue. The mixture was stirred for 1 h at room temperatureto finish condensation. The reaction solution was added 20 mL 1 M HCl, andextracted with ethyl acetate (4 × 20 mL). The combined organic phasewas dried over anhydrous Na2SO4 and finally evaporated invacuum. The residue was purified by silica-gel chromatography using mixtures ofPE/EtOAcas eluent to afford compounds 1-7.At this stage, all compounds were fully analyzed and characterized by nuclearmagnetic resonance (NMR), high resolution massspectrum (HRMS).
  • 11
  • [ 7210-76-6 ]
  • [ 1135-24-6 ]
  • (E)‐ethyl 2‐(3‐(4‐hydroxy‐3‐methoxyphenyl)acrylamido)‐4‐methylthiazolyl‐5‐carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40.2% General procedure: 0.23g (1.2mmol) ferulic acid, 0.16g (1.2mmol) 1-hydroxybenzotriazole, 0.23g (1.2mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide The hydrochloride was dissolved in 10mL N,N dimethylformamide and stirred for 30 min, 0.20g (1mmol) 2-amino-4 tert-butyl-5-nitrothiazole was added, and the temperature was raised to 115C for 16h (TLC monitoring), The reaction solution was cooled to room temperature, poured into ice water, the precipitated solid was filtered off with suction, washed with saturated sodium bicarbonate solution, dilute hydrochloric acid and water in turn, the crude product was recrystallized from ethanol to obtain a red powder (E)-N-(4-tert-butyl) -5-nitrothiazol-2-yl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide, yield 36.8%
  • 12
  • [ 1135-24-6 ]
  • [ 122902-82-3 ]
  • (E)-N-(2-((2-(1H-indol-3-yl)ethyl)amino)-2-oxoethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% General procedure: Into a stirring solution of FA (0.3 g, 1.54 mmol) in dry THF (10 mL),HOBt (0.52 g, 3.86 mmol), EDCI.HCl (0.35 g, 2.31 mmol) and DIPEA(0.49 g, 3.86 mmol) were added. The reaction was stirred at roomtemperature for 15 min. Finally, substituted amine (1.0 equiv.) wasadded, and the reaction mixture was allowed to stir overnight at roomtemperature. The progress of the reaction was monitored by TLC. Aftercompletion of the reaction, the saturated NaHCO3 solution was addedslowly into it. The mixture was extracted with ethyl acetate (3 × 50 mL),and the combined organic layer was washed with brine, dried overNa2SO4 and concentrated under vacuum. The residue was subjected tosilica gel chromatography or crystallization to afford the aforementionedtarget compounds.
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