5-Feruloylquinic Acid
(Synonyms: 5-O-阿魏酰奎尼酸) 目录号 : GC49233
A chlorogenic acid with antioxidant activity
Cas No.:40242-06-6
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
5-Feruloylquinic acid is a chlorogenic acid that has been found in green coffee beans and has antioxidant activity.1 It scavenges DPPH and superoxide anion radicals in cell-free assays (IC50s = ~9 and ~36 µM, respectively).
1.Iwai, K., Kishimoto, N., Kakino, Y., et al.In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beansJ. Agric. Food Chem.52(15)4893-4898(2004)
| Cas No. | 40242-06-6 | SDF | |
| 别名 | 5-O-阿魏酰奎尼酸 | ||
| Canonical SMILES | COC(C=C1C=CC(O[C@@H]2C[C@](O)(C[C@H]([C@@H]2O)O)C(O)=O)=O)=C(C=C1)O | ||
| 分子式 | C17H20O9 | 分子量 | 368.3 |
| 溶解度 | DMSO: soluble | 储存条件 | -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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.7152 mL | 13.5759 mL | 27.1518 mL |
| 5 mM | 0.543 mL | 2.7152 mL | 5.4304 mL |
| 10 mM | 0.2715 mL | 1.3576 mL | 2.7152 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。
Botanical and geographical characterization of green coffee (Coffea arabica and Coffea canephora): chemometric evaluation of phenolic and methylxanthine contents
J Agric Food Chem 2009 May 27;57(10):4224-35.PMID:19298065DOI:10.1021/jf8037117.
Green coffee beans of the two main commercial coffee varieties, Coffea arabica (Arabica) and Coffea canephora (Robusta), from the major growing regions of America, Africa, Asia, and Oceania were studied. The contents of chlorogenic acids, cinnamoyl amides, cinnamoyl glycosides, free phenolic acids, and methylxanthines of green coffee beans were analyzed by liquid chromatography coupled with UV spectrophotometry to determine their botanical and geographical origins. The analysis of caffeic acid, 3-feruloylquinic acid, 5-Feruloylquinic Acid, 4-feruloylquinic acid, 3,4-dicaffeoylquinic acid, 3-caffeoyl-5-feruloylquinic acid, 3-caffeoyl-4-feruloylquinic acid, 3-p-coumaroyl-4-caffeoylquinic acid, 3-caffeoyl-4-dimethoxycinnamoylquinic acid, 3-caffeoyl-5-dimethoxycinnamoylquinic acid, p-coumaroyl-N-tryptophan, feruloyl-N-tryptophan, caffeoyl-N-tryptophan, and caffeine enabled the unequivocal botanical characterization of green coffee beans. Moreover, some free phenolic acids and cinnamate conjugates of green coffee beans showed great potential as means for the geographical characterization of coffee. Thus, p-coumaroyl-N-tyrosine, caffeoyl-N-phenylalanine, caffeoyl-N-tyrosine, 3-dimethoxycinnamoyl-5-feruloylquinic acid, and dimethoxycinnamic acid were found to be characteristic markers for Ugandan Robusta green coffee beans. Multivariate data analysis of the phenolic and methylxanthine profiles provided preliminary results that allowed showing their potential for the determination of the geographical origin of green coffees. Linear discriminant analysis (LDA) and partial least-squares discriminant analysis (PLS-DA) provided classification models that correctly identified all authentic Robusta green coffee beans from Cameroon and Vietnam and 94% of those from Indonesia. Moreover, PLS-DA afforded independent models for Robusta samples from these three countries with sensitivities and specificities of classifications close to 100% and for Arabica samples from America and Africa with sensitivities of 86 and 70% and specificities to the other class of 90 and 97%, respectively.
Simultaneous identification of low-molecular weight phenolic and nitrogen compounds in craft beers by HPLC-ESI-MS/MS
Food Chem 2019 Jul 15;286:113-122.PMID:30827583DOI:10.1016/j.foodchem.2019.01.198.
Phenolic and nitrogenous compounds from different styles craft beers were identified by high performance liquid chromatography and mass spectrometry in order to stratify beer samples according to their style. For this, an exploratory assessment relying on Linear Discriminant Analysis was performed. Fifty-seven phenolic compounds were reported and twelve of them were found for the first time in beer: benzoic acids, 2,4-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, dimethoxybenzoic acid; phenolic acid conjugates, 3-p-coumaroylquinic acid, 4-p-coumaroylquinic acid, 3-feruloylquinic acid, 4-feruloylquinic acid, 5-Feruloylquinic Acid; flavonoids, taxifolin hexoside, quercetin dihexoside, apigenin-6,8-dipentoside, and isofraxidin hexoside. Additionally, 11 nitrogenous compounds belonging to the phenolamide class were found. Two discriminant functions were generated and allowed a satisfactory separation among all beer styles. 3-Caffeoylquinic acid, 3-p-coumaroylquinic acid, 4-p-coumaroylquinic acid, 5-caffeoylquinic acid, coumaric acid, kaempferol-3-O-rutinoside, proanthocyanidin B dimer III and proanthocyanidin B dimer V were the compounds that showed the highest capacity of discriminate the beer styles (IPA, Lager and Weiss).
Stimulatory Effects of Acibenzolar- S-Methyl on Chlorogenic Acids Biosynthesis in Centella asiatica Cells
Front Plant Sci 2016 Sep 28;7:1469.PMID:27733862DOI:10.3389/fpls.2016.01469.
Centella asiatica is a perrenial herb that grows in tropical regions with numerous medicinal properties mostly attributed to the presence of pentacyclic triterpenoids. Interestingly, this plant also possess a significant amount of phenylpropanoid-derived chlorogenic acids (CGAs) that have recently been reported to confer neuroprotective properties. In a biotechnological attempt to increase the biosynthesis of CGA-derivatives in cultured Centella cells, acibenzolar-S-methyl was applied as a xenobiotic inducer in combination with quinic acid and shikimic acid as precursor molecules. Applying a semi-targeted metabolomics-based approach, time and concentration studies were undertaken to evaluate the effect of the manipulation on cellular metabolism leading to CGA production. Phytochemical extracts were prepared using methanol and analyzed using a UHPLC-qTOF-MS platform. Data was processed and analyzed using multivariate data models. A total of four CGA-derivatives, annotated as trans-5-feruloylquinic acid, 3,5 di-caffeoylquinic acid, 3,5-O-dicaffeoyl-4-O-malonylquinic acid (irbic acid) and 3-caffeoyl, 5-Feruloylquinic Acid, were found to be upregulated by the acibenzolar-S-methyl treatment. To the best of our knowledge, this is the first report on the induction of CGA derivatives in this species. Contrary to expectations, the effects of precursor molecules on the levels of the CGAs were insignificant. However, a total of 16 metabolites, including CGA derivatives, were up-regulated by precursor treatment. Therefore, this study shows potential to biotechnologically manipulate C. asiatica cells to increase the production of these health beneficial CGAs.
Determination of chlorogenic acids and caffeine in homemade brewed coffee prepared under various conditions
J Chromatogr B Analyt Technol Biomed Life Sci 2017 Oct 1;1064:115-123.PMID:28918319DOI:10.1016/j.jchromb.2017.08.041.
Coffee, a complex mixture of more than 800 volatile compounds, is one of the most valuable commodity in the world, whereas caffeine and chlorogenic acids (CGAs) are the most common compounds. CGAs are mainly composed of caffeoylquinic acids (CQAs), dicaffeoylquinic acids (diCQAs), and feruloylquinic acids (FQAs). The major CGAs in coffee are neochlorogenic acid (3-CQA), cryptochlorogenic acid (4-CQA), and chlorogenic acid (5-CQA). Many studies have shown that it is possible to separate the isomers of FQAs by high-performance liquid chromatography (HPLC). However, some authors have shown that it is not possible to separate 4-feruloylquinic acid (4-FQA) and 5-Feruloylquinic Acid (5-FQA) by HPLC. Therefore, the present study was designated to investigate the chromatographic problems in the determination of CGAs (seven isomers) and caffeine using HPLC-DAD. The values of determination coefficient (R2) calculated from external-standard calibration curves were >0.998. The recovery rates conducted at 3 spiking levels ranged from 99.4% to 106.5% for the CGAs and from 98.8% to 107.1% for the caffeine. The precision values (expressed as relative standard deviations (RSDs)) were <7% and <3% for intra and interday variability, respectively. The tested procedure proved to be robust. The seven CGAs isomers except 4-FQA and 5-FQA were well distinguished and all gave good peak shapes. We have found that 4-FQA and 5-FQA could not be separated using HPLC. The method was extended to investigate the effects of different brewing conditions such as the roasting degree of green coffee bean, coffee-ground size, and numbers of boiling-water pours, on the concentration of CGAs and caffeine in homemade brewed coffee, using nine green coffee bean samples of different origins. It was reported that medium-roasted, fine-ground coffees brewed using three pours of boiling water were the healthiest coffee with fluent CGAs.
In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans
J Agric Food Chem 2004 Jul 28;52(15):4893-8.PMID:15264931DOI:10.1021/jf040048m.
Seven kinds of hydroxycinnamic acid derivatives identified as 3-caffeoylquinic acid (3-CQA), 4-caffeolyquinic acid (4-CQA), 5-caffeoylquinic acid (5-CQA), 5-Feruloylquinic Acid (5-FQA), 3,4-dicaffeoylquinic acid (3,4-diCQA), 3,5-dicaffeoylquinic acid (3,5-diCQA), and 4,5-dicaffoylquinic acid (4,5-diCQA) by MS, 1H NMR, and HPLC analyses were isolated from low-quality (immature) and commercial quality green coffee beans. The quantity of chlorogenic acid isomers (10.4 g/100 g), especially 5-CQA, in commercial green coffee beans [West Indische Bereiding (West India processing beans from Sumatra Island, Indonesia, WIB)] was higher than that in low-quality beans [9.1 g/100 g, Eerste Kwaliteit (Export low-quality beans from Java Island, Indonesia, EK-1, grade 4)], whereas little difference in diCQAs was detected between the two kinds of beans. The free radical scavenging activity of these isolates was evaluated in assay systems using DPPH free radicals and superoxide anion radicals generated by xanthine-XOD. The diCQAs showed strong (1.0-1.8-fold) free radical scavenging activity compared to commonly used antioxidants such as alpha-tocopherol and ascorbic acid. The potency order of superoxide anion radical scavenging activity was diCQAs > caffeic acid, CQAs > 5-FQA. The activities of the diCQAs were twice as effective as those of CQAs and 4 times as effective as that of 5-FQA. The diCQAs also exhibited more potent (2.0-2.2-fold) tyrosinase inhibitory activities compared to CQAs, arbutin, and ascorbic acid. The isolates exhibited antiproliferation activities in four cancer cell lines, U937, KB, MCF7, and WI38-VA. Among these, KB cells were most sensitive (IC50 = 0.10-0.56 mM).