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Chemical Structure| 501-97-3 Chemical Structure| 501-97-3
Chemical Structure| 501-97-3

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Phloretic Acid can defense influenza through augmentation of type I interferon signaling, it's a microbially associated metabolite and a naturally occurring phenolic compound.

Synonyms: Desaminotyrosine; 3-(4-Hydroxyphenyl)propionic acid; NSC 40949

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Product Citations

Product Citations

Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto ; Prathamesh M. Datar ; Daniel J. DiRocco ; Katherine Huntera and E. Neil G. Marsh

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ∼35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

Alternative Products

Product Details of p-hydroxyl phenylpropanol

CAS No. :501-97-3
Formula : C9H10O3
M.W : 166.17
SMILES Code : C1=C(C=CC(=C1)O)CCC(O)=O
Synonyms :
Desaminotyrosine; 3-(4-Hydroxyphenyl)propionic acid; NSC 40949
MDL No. :MFCD00002778
InChI Key :NMHMNPHRMNGLLB-UHFFFAOYSA-N
Pubchem ID :10394

Safety of p-hydroxyl phenylpropanol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of p-hydroxyl phenylpropanol

* 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 [ 501-97-3 ]

[ 501-97-3 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 60211-57-6 ]
  • [ 29022-11-5 ]
  • [ 501-97-3 ]
  • resin-bound phenol [ No CAS ]
  • {3-[4-(3,5-dichloro-benzyloxy)-phenyl]-propionylamino}-acetic acid [ No CAS ]
  • 2
  • [ 32566-01-1 ]
  • [ 501-97-3 ]
  • [ 677297-20-0 ]
YieldReaction ConditionsOperation in experiment
55% 3-(4-Hydroxy-phenyl)-N-[2-(1H-indol-2-yl)-phenyl]-propionamide Prepared from 2-(2-aminophenyl) indole and 3-(4-hydroxyphenyl) propionic acid in 55% yield following procedure 1. The product was chromatographed on silica and crystallized from acetonitrile. 100% Purity by LC/MS (230 DAD), Mass-spec [M+H+]=357, 1H NMR (MeOH-d4): 2.61 t, 7.4 Hz (1H), 2.89 t, 7.4 Hz (1H), 6.37 s (1H), 6.72 d, 8 Hz (2H), 7.00-7.06 m (3H), 7.11 t, 7 Hz (1H), 7.27-7.35 m (2H), 7.38 d, 8 Hz (1H), 7.54 d, 7 Hz (1H), 7.58 dd, 7,1 Hz (1H), 7.67 d, 8 Hz (1H).
  • 3
  • [ 501-97-3 ]
  • potash [ No CAS ]
  • [ 4654-08-4 ]
  • 4
  • [ 936571-71-0 ]
  • [ 501-97-3 ]
  • [ 1791-13-5 ]
  • [ 1427752-38-2 ]
YieldReaction ConditionsOperation in experiment
4.7 mg Example A1 To a solution of di-tert-butyl L-aspartate hydrochloride (40 mumoL) were added 0.5 mL of a solution of 3-(4-hydroxyphenyl)propionic acid (299 mg) and 4-dimethylaminopyridine (220 mg) in N,N-dimethylformamide (30 mL), and 0.5 mL of a solution of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (518 mg) in N,N-dimethylformamide (30 mL), followed by stirring at room temperature overnight. After concentrating under reduced pressure, 1.0 mL of a solution of 4-[N',N'-bis(tert-butoxycarbonyl)carbamimidamido]benzoic acid (911 mg) in dichloromethane (60 mL) and 0.5 mL of a solution of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (518 mg) in dichloromethane (30 mL) were added thereto, followed by stirring at room temperature overnight. Trifluoroacetic acid (0.5 mL) was added thereto, followed by stirring further at room temperature overnight. After concentrating under reduced pressure, the product was preparatively purified with LC (aqueous formic acid solution/methanol) by means of an MS trigger, and then concentrated under reduced pressure to obtain N-(3-{4-[(4-carbamimidamidobenzoyl)oxy]phenyl}propanoyl)-L-aspartic acid (4.7 mg).
YieldReaction ConditionsOperation in experiment
General procedure: FIGURES 8A-8C are illustrations of the hydroxylation of arenes mediated by 4,5-dichlorophthaloyl peroxide. To examine the scope of the hydroxylation reaction mediated by 4,5-dichlorophthaloyl peroxide (2), two general sets of reaction conditions were developed. The oxidations are carried out using either 1.3 equivalents of 4,5-dichlorophthaloyl peroxide (2) at 50 C or 2.5 equivalents heated to 75 C. Operationally the reaction proceeds without the need for special exclusion of air and the use of commercial grade HFIP is sufficient. Thermogravimetric analysis indicates that 4,5-dichlorophthaloyl peroxide has a point of decomposition at 135 C. Therefore, all reactions reported are conducted at or below 75 C. While we have not encountered exothermic reactions, appropriate precautions must be used similar to those for all experiments using peroxides. Isolated yields are given below each entry. The yield in parentheses refers to the starting material recovered. The minor regioisomeric positions are labeled with the respective carbon atom number and, after the major isomer, listed sequentially. Reaction conducted at 0C. Prior to the addition of 4,5-dichlorophthaloyl peroxide (2) p-toluenesulfonic acid monohydrate (1.0 equiv.) was added to the solution of 3(y).
  • 6
  • [ 501-52-0 ]
  • [ 495-78-3 ]
  • [ 501-97-3 ]
  • 7
  • [ 207399-07-3 ]
  • [ 501-97-3 ]
  • C45H53N2O3(1+)*I(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 5h; 500 mg (0.92 mmol, 1 eq) of the compound prepared in Step 2 of Preparation Example 3 was dissolved in 2.5 mL of DMF, 255.6 mg (1.85 mmol, 2 eq) of potassium carbonate and307.4 mg (1.85 mmol, 2 eq) of 3- (4-hydroxyphenyl) propionic acid was added and the mixture was stirred at 40 C for 5 hours. After completion of the reaction, 120 mL of ethyl acetate was added to form crystals, followed by filtration and drying under reduced pressure. Purification by silica gel column chromatography with chloroform: methyl alcohol (6: 1) yielded pure compound 7-3. (62.0 mg, 10%).
 

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