Desaminotyrosine (3-(4-Hydroxyphenyl)propionic acid)
(Synonyms: 对羟基苯丙酸; 3-(4-Hydroxyphenyl)propionic acid) 目录号 : GC33930
Phloretic acid (Desaminotyrosine, Hydro-p-coumaric acid, Phloretate, 3-(4-Hydroxyphenyl)propanoic acid) is a naturally occurring phenolic compound which can be produced by the hydrogenation of p-coumaric acid or synthesized from phloretin, a by-product of apple tree leaves.
Cas No.:501-97-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Animal experiment: | Mice[1]Indicated mice receive 200 mM Desaminotyrosine dissolved in Kool-Aid in the drinking water (control animals receive Kool-Aid alone). Indicated mice receive poly(IC) injections of 1 mg/kg for vancomycin, neomycin, ampicillin, and metronidazole (VNAM) treated mice or 5 mg/kg for all other mice intraperitoneally daily for 4 days, and then mice are scarified on day five at which time serum is collected[1]. |
References: [1]. Steed AL, et al. The microbial metabolite desaminotyrosine protects from influenza through type I interferon. Science. 2017 Aug 4;357(6350):498-502. | |
Phloretic acid (Desaminotyrosine, Hydro-p-coumaric acid, Phloretate, 3-(4-Hydroxyphenyl)propanoic acid) is a naturally occurring phenolic compound which can be produced by the hydrogenation of p-coumaric acid or synthesized from phloretin, a by-product of apple tree leaves.
| Cas No. | 501-97-3 | SDF | |
| 别名 | 对羟基苯丙酸; 3-(4-Hydroxyphenyl)propionic acid | ||
| Canonical SMILES | C1=C(C=CC(=C1)O)CCC(O)=O | ||
| 分子式 | C9H10O3 | 分子量 | 166.18 |
| 溶解度 | DMSO : ≥ 300 mg/mL (1805.27 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.0176 mL | 30.0879 mL | 60.1757 mL |
| 5 mM | 1.2035 mL | 6.0176 mL | 12.0351 mL |
| 10 mM | 0.6018 mL | 3.0088 mL | 6.0176 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Use of 3-(4-Hydroxyphenyl\)propionic acid as electron donating compound in a potentiometric aflatoxin M1-immunosensor
Anal Chim Acta 2010 Feb 19;661(1):122-7.PMID:20113725DOI:10.1016/j.aca.2009.12.017.
We developed a potentiometric aflatoxin M(1)-immunosensor which utilizes 3-(4-Hydroxyphenyl\)propionic acid (p-HPPA) as electron donating compound for horseradish peroxidase (HRP; EC 1.11.1.7). The assay system consists of a polypyrrole-surface-working electrode coated with a polyclonal anti-M(1) antibody (pAb-AFM(1)), a Ag/AgCl reference electrode and a HRP-aflatoxin B(1) conjugate (HRP-AFB(1) conjugate). To optimize the potentiometric measuring system p-HPPA as well as related compounds serving as electron donating compounds were compared. Also the influence of different buffer systems, varying pH and substrate concentrations on signal intensity was investigated. Our results suggest that reaction conditions that favor the formation of Pummerer's type ketones lead to an increase in signal intensity rather than formation of fluorescent dye. Comparison with commercial ready-to-use HRP electron donating compounds such as 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), o-phenylenediamine (OPD) or 3,3',5,5'-tetramethylbenzidine (TMB) showed that only 34%, 77% and 49% of the signal intensity of p-HPPA were reached, respectively. The optimized assay had a detection limit of 40 pg mL(-1) and allowed detection of 500 pg mL(-1) (FDA action limit) aflatoxin M(1) (AFM(1)) in pasteurized milk and UHT-milk containing 0.3-3.8% fat within 10 min without any sample treatment. The working range was between 250 and 2000 pg mL(-1) AFM(1).
Human intestinal microbial metabolism of naringin
Eur J Drug Metab Pharmacokinet 2015 Sep;40(3):363-7.PMID:24935725DOI:10.1007/s13318-014-0193-x.
Naringin, a major flavonoid in citrus fruits, has been proved to be a promising antitussive candidate. It undertakes complicated metabolism. In this study, human intestinal microbial metabolism of naringin was studied in vitro. Six persons' fecal water, which have intestinal microbial enzyme, were used in the first experiment. Naringin was metabolized by fecal water into naringenin. Subsequently, 3-(4-Hydroxyphenyl\)propionic acid (4-HPPA) was produced with naringenin degradation by a person's fecal water. However, 4-HPPA was not detected after naringenin degradation by the other 5 subjects' fecal water and the reason might be that the degrading velocity of 4-HPPA exceeded the producing velocity. To confirm the difference in degrading 4-HPPA among human feces, 22 healthy persons' feces were used for incubation. In this second experiment, 15 persons' feces could degrade 4-HPPA, but the other 7 subjects' could not. Human feces showed different ability of degrading 4-HPPA, and there are no gender differences. These results may be helpful for explaining findings in pharmacological and toxicological studies and are groundwork for clinical studies.
Influence of Intestinal Microbiota on the Catabolism of Flavonoids in Mice
J Food Sci 2016 Dec;81(12):H3026-H3034.PMID:27792839DOI:10.1111/1750-3841.13544.
Although in vitro studies have shown that flavonoids are metabolized into phenolic acids by the gut microbiota, the biotransformation of flavonoids by intestinal microbiota is seldom studied in vivo. In this study, we investigated the impact of the gut microbiota on the biotransformation of 3 subclasses of flavonoids (flavonols, flavones, and flavanones). The ability of intestinal microbiota to convert flavonoids was confirmed with an in vitro fermentation model using mouse gut microflora. Simultaneously, purified flavonoids were administered to control and antibiotic-treated mice by gavage, and the metabolism of these flavonoids was evaluated. p-Hydroxyphenylacetic acid, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, hydrocaffeic acid, coumaric acid, and 3-(4-Hydroxyphenyl\)propionic acid were detected in the serum samples from the control mice after flavonoid consumption. The serum flavonoid concentrations were similar in both groups, whereas the phenolic metabolite concentrations were lower in the antibiotic-treated mice than in the control mice. We detected markedly higher flavonoids excretion in the feces and urine of the antibiotic-treated mice compared to the controls. Moreover, phenolic metabolites were upregulated in the control mice. These results suggest that the intestinal microbiota are not necessary for the absorption of flavonoids, but are required for their transformation.
Effects of reduced phenolic acids on metabolism of propionate and palmitate in bovine liver tissue in vitro
J Dairy Sci 1994 Dec;77(12):3608-17.PMID:7699139DOI:10.3168/jds.S0022-0302(94)77305-7.
Benzoic acid, 3-phenylpropionic acid, trans-cinnamic acid, and 3-(4-Hydroxyphenyl\)propionic acid in ruminal fluid are presumed to be the products of chemical reduction of dietary phenolic monomers by ruminal microorganisms. Effects of reduced phenolics on metabolism in bovine liver tissue were evaluated by measurement of 1) conversion of propionate to glucose and CO2, 2) conversion of palmitate to oxidized products, and 3) leakage of lactate dehydrogenase from liver slices in vitro. In Experiment 1, .4 mM benzoic, 3-phenylpropionic, trans-cinnamic, or 3-(4-hydroxyphenyl)propionic acids decreased conversion of propionate to glucose and decreased conversion of palmitate to total oxidation products. At .2 mM, 3-(4-Hydroxyphenyl\)propionic acid did not inhibit conversion of propionate to glucose compared with that of controls, but the other reduced phenolics did. In Experiment 2, the same reduced phenolics inhibited conversion of propionate to glucose. Of the reduced phenolics tested, cinnamic acid inhibited conversion of propionate to glucose at the lowest concentration, .1 mM. Additionally, when present at > or = .4, .1, or .005 mM, benzoic, 3-phenylpropionic, or trans-cinnamic acids, respectively, increased leakage of lactate dehydrogenase from liver tissue. The reduced phenolics tested, which are representative of those in ruminal fluid, inhibited metabolism of bovine liver tissue in vitro at supraphysiological concentrations. Data at physiological concentrations were inconclusive.
Exploring recombinant flavonoid biosynthesis in metabolically engineered Escherichia coli
Chembiochem 2004 Apr 2;5(4):500-7.PMID:15185374DOI:10.1002/cbic.200300783.
Flavonoids are important plant-specific secondary metabolites synthesized from 4-coumaroyl coenzyme A (CoA), derived from the general phenylpropanoid pathway, and three malonyl-CoAs. The synthesis involves a plant type III polyketide synthase, chalcone synthase. We report the cloning and coexpression in Escherichia coli of phenylalanine ammonia lyase, cinnamate-4-hydroxylase, 4-coumarate:CoA ligase, and chalcone synthase from the model plant Arabidopsis thaliana. Simultaneous expression of all four genes resulted in a blockage after the first enzymatic step caused by the presence of nonfunctional cinnamate-4-hydroxylase. To overcome this problem we fed exogenous 4-coumaric acid to induced cultures. We observed high-level production of the flavanone naringenin as a result. We were also able to produce phloretin by feeding cultures with 3-(4-Hydroxyphenyl\)propionic acid. Feeding with ferulic or caffeic acid did not yield the corresponding flavanones. We have also cloned and partially characterized a new tyrosine ammonia lyase from Rhodobacter sphaeroides. Tyrosine ammonia lyase was substituted for phenylalanine ammonia lyase and cinnamate-4-hydroxylase in our E. coli clones and three different growth media were tested. After 48 h induction, high-level production (20.8 mg L(-1)) of naringenin in metabolically engineered E. coli was observed for the first time.