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4-O-beta-Glucopyranosyl-cis-coumaric acid

CAS# 117405-48-8

4-O-beta-Glucopyranosyl-cis-coumaric acid

Catalog No. BCN1608----Order now to get a substantial discount!

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Quality Control of 4-O-beta-Glucopyranosyl-cis-coumaric acid

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Chemical structure

4-O-beta-Glucopyranosyl-cis-coumaric acid

3D structure

Chemical Properties of 4-O-beta-Glucopyranosyl-cis-coumaric acid

Cas No. 117405-48-8 SDF Download SDF
PubChem ID 10604651 Appearance Powder
Formula C15H18O8 M.Wt 326.29
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (Z)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
SMILES C1=CC(=CC=C1C=CC(=O)O)OC2C(C(C(C(O2)CO)O)O)O
Standard InChIKey LJFYQZQUAULRDF-LSSWKVNRSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 4-O-beta-Glucopyranosyl-cis-coumaric acid

The herbs of Trifolium pratense

Protocol of 4-O-beta-Glucopyranosyl-cis-coumaric acid

Structure Identification
Food Chemistry, 2002, 76(2):207-212.

Polymeric fractions containing phenol glucosides in flaxseed.[Reference: WebLink]


METHODS AND RESULTS:
Extract rich in phenolic compounds was obtained from flaxseed with 1,4-dioxane:ethanol (1:1, v/v). This extract (whole polymer) was fractionated by solid-phase extraction into three “polymeric” fractions of comparable polarity. HPLC analyses of the base hydrolysates of the three polymeric fractions showed that they contain the same UV-absorbing components, though at different levels and all contained substantial amounts of a lignan, secoisolariciresinoldiglucoside (SDG). Fractionation of the base hydrolysates by column chromatography, followed by high performance liquid chromatography (HPLC) yielded two pure hydroxycinnamic acid derivatives; 4-O-β-d-glucopyranosyl-p-coumaric acid(4-O-beta-Glucopyranosyl-cis-coumaric acid) and 4-O-β-d-glucopyranosylferulic acid, whose structures were identified by nuclear magnetic resonance spectroscopy (NMR). NMR analysis showed all three polymeric fractions to have phenolic and aliphatic components and, in line with HPLC, suggested some structural variations between these fractions.
CONCLUSIONS:
The results of this study suggest that the glucosylated phenolic compounds of flaxseed exist in polymeric structure(s) containing ester linkages.

4-O-beta-Glucopyranosyl-cis-coumaric acid Dilution Calculator

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4-O-beta-Glucopyranosyl-cis-coumaric acid Molarity Calculator

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Preparing Stock Solutions of 4-O-beta-Glucopyranosyl-cis-coumaric acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0648 mL 15.3238 mL 30.6476 mL 61.2952 mL 76.619 mL
5 mM 0.613 mL 3.0648 mL 6.1295 mL 12.259 mL 15.3238 mL
10 mM 0.3065 mL 1.5324 mL 3.0648 mL 6.1295 mL 7.6619 mL
50 mM 0.0613 mL 0.3065 mL 0.613 mL 1.2259 mL 1.5324 mL
100 mM 0.0306 mL 0.1532 mL 0.3065 mL 0.613 mL 0.7662 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 4-O-beta-Glucopyranosyl-cis-coumaric acid

The value of grip test, lysophosphatidlycholines, glycerophosphocholine, ornithine, glucuronic acid decrement in assessment of nutritional and metabolic characteristics in hepatitis B cirrhosis.[Pubmed:28384211]

PLoS One. 2017 Apr 6;12(4):e0175165.

The liver is essential for the regulation of energy, protein and amino acids, as well as in other aspects of metabolism. To identify efficient indexes for evaluation of nutritional status and metabolic characteristics during different Child-Pugh stages of hepatitis B cirrhosis, 83 patients and 35 healthy individuals were enrolled in our study. We found that grip strength, triceps skinfold thickness (TSF), body fat and skeletal muscle of the patients were reduced compared to the control group (P<0.05). Ultra-high-performance liquid chromatography data combined with mass spectrometry (UPLC-MS) showed that levels of a variety of metabolites, including lysophosphatidylcholines (LysoPCs), glycerophosphocholine, ornithine and glucuronic acid were reduced in the serum of patients with hepatitis B cirrhosis (P<0.001). However, glycerophosphoserine and taurocholic acid levels were higher than in the control group (P<0.001). Moreover, grip strength was correlated with the Child-Pugh score (P<0.05). Serum albumin, total cholesterol, LDL, LysoPCs, glycerophosphocholine, ornithine, glucuronic acid, glycerophosphoserine and taurocholic acid were correlated with the Child-Pugh score (P<0.01). These findings suggested that grip strength and the above small molecular substances might be considered as sensitive and important indexes for evaluating nutritional status and metabolic characteristics of patients with hepatitis B cirrhosis, which may help assess prognosis and adjust nutritional treatment.

Prevention of TGF-beta-induced early liver fibrosis by a maleic acid derivative anti-oxidant through suppression of ROS, inflammation and hepatic stellate cells activation.[Pubmed:28384213]

PLoS One. 2017 Apr 6;12(4):e0174008.

Current anti-fibrotic effect of antioxidants in vivo is disappointing due probably to the fact that once liver fibrogenesis is established it is too advanced to be reversed by anti-oxidation mechanism. We consider antioxidant may only act on the early phase of fibrogenesis. Thus, we had previously established an early liver fibrosis animal model using an inducible expression vector (pPK9a), which contains TGF-beta gene and was hydro-dynamically transferred into mice to induce a transient liver fibrosis. TGF-beta1 has been well documented to up-regulate the expression of alpha2(1) collagen (Col 1A2) gene in the liver via the reactive oxygen species (ROS); the process triggers inflammation, leading to hepatic stellate cells (HSC) activation and liver fibrogenesis. Using our animal model and ROS, cyclooxygenase-2 (Cox-2) and Col 1A2 promoter assays as screening targets, we report here that a maleic acid derivative isolated from the Antrodia camphorata mycelium strongly decreases ROS production, promoter activity of Cox-2 and Col 1A2, intracellular calcium, expression of alpha-smooth muscle actin (alpha-SMA), Smad4-p-Smad2/3 co-localization in cell nucleus and the DNA binding activity of Sp1. Our results suggest that the maleic acid derivative prevents liver fibrosis at an early phase both in vitro and in vivo through the inhibition of ROS, inflammation and the activation of HSC.

Thermo-acid-stable phytase-mediated enhancement of bioethanol production using Colocasia esculenta.[Pubmed:28384593]

Bioresour Technol. 2017 Jul;235:396-404.

Phytase production by the thermophilic mould Thermomyces lanuginosus SSBP was enhanced 8.56-fold in submerged fermentation, which was further improved in fed-batch cultivations. The protein was purified to homogeneity using ammonium sulphate precipitation, Resource Q anion exchange and Superdex gel-filtration chromatography, with an overall purification of 24.7-fold and a yield of 5.16%. The purified 49kDa protein was optimally active at 55 degrees C and pH 5.0, and was stable between 50 and 90 degrees C from pH 3.0-6.0, with a half-life of 138.6min at 70 degrees C. It was moderately stimulated by Ba(+2) and Mg(+2). The enzyme reduced phytate content in Colocasia esculenta starch (from 1.43mg/g to 0.05mg/g) that resulted in an improvement in the availability of fermentable sugars with a concomitant reduction in viscosity and 1.59-fold improvement in ethanol production. Thermo-acid-stable phytase from T. lanuginosus SSBP could be of major biotechnological interest, especially due to its robustness and wide applicability.

Description

4-O-beta-Glucopyranosyl-cis-coumaric acid is a natural compound isolated formn Nelumbo nucifera Gaertn.

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