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xylitol pentacetate

CAS# 13437-68-8

xylitol pentacetate

Catalog No. BCN6267----Order now to get a substantial discount!

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Quality Control of xylitol pentacetate

Number of papers citing our products

Chemical structure

xylitol pentacetate

3D structure

Chemical Properties of xylitol pentacetate

Cas No. 13437-68-8 SDF Download SDF
PubChem ID 12939086 Appearance White cryst.
Formula C15H22O10 M.Wt 362.33
Type of Compound Miscellaneous Storage Desiccate at -20°C
Synonyms D-Ribitol pentaacetate;xylitol pentaacetate
Solubility >6.6mg/mL in DMSO
Chemical Name [(2R,4S)-2,3,4,5-tetraacetyloxypentyl] acetate
SMILES CC(=O)OCC(C(C(COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Standard InChIKey NVKPIAUSOPISJK-YIONKMFJSA-N
Standard InChI InChI=1S/C15H22O10/c1-8(16)21-6-13(23-10(3)18)15(25-12(5)20)14(24-11(4)19)7-22-9(2)17/h13-15H,6-7H2,1-5H3/t13-,14+,15?
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 xylitol pentacetate

The roots of Primula officinalis

Biological Activity of xylitol pentacetate

DescriptionXylitol, a commonly used sweetener, it can inhibit the growth of pneumococci, it is effective in preventing otitis media and decreasing the need for antimicrobials when xylitol sugar given in a syrup or chewing gum. Xylitol is also a widely used anti-caries agent that has anti-inflammatory and anti-cancer effects, it inhibits salivary lysozyme activity.
TargetsAntifection | Autophagy
In vitro

The effects of xylitol and sorbitol on lysozyme- and peroxidase-related enzymatic and candidacidal activities.[Pubmed: 25874813]

Arch Oral Biol. 2015 Mar 30;60(7):998-1006.

To investigate whether Xylitol and sorbitol affect enzymatic and candidacidal activities of lysozyme, the peroxidase system, and the glucose oxidase-mediated peroxidase system.
METHODS AND RESULTS:
Xylitol and sorbitol were added to hen egg-white lysozyme, bovine lactoperoxidase, glucose oxidase-mediated peroxidase, and whole saliva in solution and on hydroxyapatite surfaces. The enzymatic activities of lysozyme, peroxidase, and glucose oxidase-mediated peroxidase were determined by the turbidimetric method, the NbsSCN assay, and production of oxidized o-dianisidine, respectively. Candidacidal activities were determined by comparing colony forming units using Candida albicans ATCC strains 10231, 11006, and 18804. While Xylitol and sorbitol did not affect the enzymatic activity of hen egg-white lysozyme both in solution and on hydroxyapatite surfaces, they did inhibit the enzymatic activity of salivary lysozyme significantly in solution, but not on the surfaces. Xylitol and sorbitol enhanced the enzymatic activities of both bovine lactoperoxidase and salivary peroxidase significantly in a dose-dependent manner in solution, but not on the surfaces. Sorbitol, but not Xylitol, inhibited the enzymatic activity of glucose oxidase-mediated peroxidase significantly. Both Xylitol and sorbitol did not affect candidacidal activities of hen egg-white lysozyme, the bovine lactoperoxidase system, or the glucose oxidase-mediated bovine lactoperoxidase system.
CONCLUSIONS:
Xylitol and sorbitol inhibited salivary lysozyme activity, but enhanced both bovine lactoperoxidase and salivary peroxidase activities significantly in solution. Xylitol and sorbitol did not augment lysozyme- and peroxidase-related candidacidal activities.

Xylitol, an anticaries agent, exhibits potent inhibition of inflammatory responses in human THP-1-derived macrophages infected with Porphyromonas gingivalis.[Pubmed: 24592909]

J Periodontol. 2014 Jun;85(6):e212-23.

Xylitol is a well-known anticaries agent and has been used for the prevention and treatment of dental caries. In this study, the anti-inflammatory effects of Xylitol are evaluated for possible use in the prevention and treatment of periodontal infections.
METHODS AND RESULTS:
Cytokine expression was stimulated in THP-1 (human monocyte cell line)-derived macrophages by live Porphyromonas gingivalis, and enzyme-linked immunosorbent assay and a commercial multiplex assay kit were used to determine the effects of Xylitol on live P. gingivalis-induced production of cytokine. The effects of Xylitol on phagocytosis and the production of nitric oxide were determined using phagocytosis assay, viable cell count, and Griess reagent. The effects of Xylitol on P. gingivalis adhesion were determined by immunostaining, and costimulatory molecule expression was examined by flow cytometry. Live P. gingivalis infection increased the production of representative proinflammatory cytokines, such as tumor necrosis factor-α and interleukin (IL)-1β, in a multiplicity of infection- and time-dependent manner. Live P. gingivalis also enhanced the release of cytokines and chemokines, such as IL-12 p40, eotaxin, interferon γ-induced protein 10, monocyte chemotactic protein-1, and macrophage inflammatory protein-1. The pretreatment of Xylitol significantly inhibited the P. gingivalis-induced cytokines production and nitric oxide production. In addition, Xylitol inhibited the attachment of live P. gingivalis on THP-1-derived macrophages. Furthermore, Xylitol exerted antiphagocytic activity against both Escherichia coli and P. gingivalis.
CONCLUSIONS:
These findings suggest that Xylitol acts as an anti-inflammatory agent in THP-1-derived macrophages infected with live P. gingivalis, which supports its use in periodontitis.

In vivo

A novel use of xylitol sugar in preventing acute otitis media.[Pubmed: 9755259]

Pediatrics. 1998 Oct;102(4 Pt 1):879-84.

Xylitol, a commonly used sweetener, is effective in preventing dental caries. As it inhibits the growth of pneumococci, we evaluated whether Xylitol could be effective in preventing acute otitis media (AOM).
METHODS AND RESULTS:
Altogether, 857 healthy children recruited from day care centers were randomized to one of five treatment groups to receive control syrup (n = 165), Xylitol syrup (n = 159), control chewing gum (n = 178), Xylitol gum (n = 179), or Xylitol lozenge (n = 176). The daily dose of Xylitol varied from 8.4 g (chewing gum) to 10 g (syrup). The design was a 3-month randomized, controlled trial, blinded within the chewing gum and syrup groups. The occurrence of AOM each time the child showed any symptoms of respiratory infection was the main outcome. Although at least one event of AOM was experienced by 68 (41%) of the 165 children who received control syrup, only 46 (29%) of the 159 children receiving Xylitol syrup were affected, for a 30% decrease (95% confidence interval [CI]: 4.6%-55.4%). Likewise, the occurrence of otitis decreased by 40% compared with control subjects in the children who received Xylitol chewing gum (CI: 10.0%-71.1%) and by 20% in the lozenge group (CI: -12.9%-51.4%). Thus, the occurrence of AOM during the follow-up period was significantly lower in those who received Xylitol syrup or gum, and these children required antimicrobials less often than did controls. Xylitol was well tolerated.
CONCLUSIONS:
Xylitol sugar, when given in a syrup or chewing gum, was effective in preventing AOM and decreasing the need for antimicrobials.

Protocol of xylitol pentacetate

Cell Research

Xylitol induces cell death in lung cancer A549 cells by autophagy.[Pubmed: 25650339]

Biotechnol Lett. 2015 May;37(5):983-90.

Xylitol is a widely used anti-caries agent that has anti-inflammatory effects. We have evaluated the potential of Xylitol in cancer treatment.
METHODS AND RESULTS:
It's effects on cell proliferation and cytotoxicity were measured by MTT assay and LDH assay. Cell morphology and autophagy were examined by immunostaining and immunoblotting. Xylitol inhibited cell proliferation in a dose-dependent manner in these cancer cells: A549, Caki, NCI-H23, HCT-15, HL-60, K562, and SK MEL-2. The IC50 of Xylitol in human gingival fibroblast cells was higher than in cancer cells, indicating that it is more specific for cancer cells. Moreover, Xylitol induced autophagy in A549 cells that was inhibited by 3-methyladenine, an autophagy inhibitor.
CONCLUSIONS:
These results indicate that Xylitol has potential in therapy against lung cancer by inhibiting cell proliferation and inducing autophagy of A549 cells.

xylitol pentacetate Dilution Calculator

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xylitol pentacetate Molarity Calculator

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Preparing Stock Solutions of xylitol pentacetate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7599 mL 13.7996 mL 27.5991 mL 55.1983 mL 68.9979 mL
5 mM 0.552 mL 2.7599 mL 5.5198 mL 11.0397 mL 13.7996 mL
10 mM 0.276 mL 1.38 mL 2.7599 mL 5.5198 mL 6.8998 mL
50 mM 0.0552 mL 0.276 mL 0.552 mL 1.104 mL 1.38 mL
100 mM 0.0276 mL 0.138 mL 0.276 mL 0.552 mL 0.69 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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Background on xylitol pentacetate

Xylitol is a chemical categorized as a polyalcohol or sugar alcohol. Target: Others Xylitol is a chemical categorized as a polyalcohol or sugar alcohol (alditol). Xylitol has the formula (CHOH)3(CH2OH)2 and is an achiral isomer of pentane-1,2,3,4,5-pentol. Xylitol is used as a diabetic sweetener which is roughly as sweet as sucrose with 33% fewer calories. Unlike other natural or synthetic sweeteners, xylitol is actively beneficial for dental health by reducing caries to a third in regular use and helpful to remineralization. Xylitol is naturally found in low concentrations in the fibers of many fruits and vegetables, and can be extracted from various berries, oats, and mushrooms, as well as fibrous material such as corn husks and sugar cane bagasse and birch.

References:
[1]. http://en.wikipedia.org/wiki/Xylitol

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References on xylitol pentacetate

Xylitol induces cell death in lung cancer A549 cells by autophagy.[Pubmed:25650339]

Biotechnol Lett. 2015 May;37(5):983-90.

Xylitol is a widely used anti-caries agent that has anti-inflammatory effects. We have evaluated the potential of xylitol in cancer treatment. It's effects on cell proliferation and cytotoxicity were measured by MTT assay and LDH assay. Cell morphology and autophagy were examined by immunostaining and immunoblotting. Xylitol inhibited cell proliferation in a dose-dependent manner in these cancer cells: A549, Caki, NCI-H23, HCT-15, HL-60, K562, and SK MEL-2. The IC50 of xylitol in human gingival fibroblast cells was higher than in cancer cells, indicating that it is more specific for cancer cells. Moreover, xylitol induced autophagy in A549 cells that was inhibited by 3-methyladenine, an autophagy inhibitor. These results indicate that xylitol has potential in therapy against lung cancer by inhibiting cell proliferation and inducing autophagy of A549 cells.

A novel use of xylitol sugar in preventing acute otitis media.[Pubmed:9755259]

Pediatrics. 1998 Oct;102(4 Pt 1):879-84.

BACKGROUND: Xylitol, a commonly used sweetener, is effective in preventing dental caries. As it inhibits the growth of pneumococci, we evaluated whether xylitol could be effective in preventing acute otitis media (AOM). DESIGN: Altogether, 857 healthy children recruited from day care centers were randomized to one of five treatment groups to receive control syrup (n = 165), xylitol syrup (n = 159), control chewing gum (n = 178), xylitol gum (n = 179), or xylitol lozenge (n = 176). The daily dose of xylitol varied from 8.4 g (chewing gum) to 10 g (syrup). The design was a 3-month randomized, controlled trial, blinded within the chewing gum and syrup groups. The occurrence of AOM each time the child showed any symptoms of respiratory infection was the main outcome. RESULTS: Although at least one event of AOM was experienced by 68 (41%) of the 165 children who received control syrup, only 46 (29%) of the 159 children receiving xylitol syrup were affected, for a 30% decrease (95% confidence interval [CI]: 4.6%-55.4%). Likewise, the occurrence of otitis decreased by 40% compared with control subjects in the children who received xylitol chewing gum (CI: 10.0%-71.1%) and by 20% in the lozenge group (CI: -12.9%-51.4%). Thus, the occurrence of AOM during the follow-up period was significantly lower in those who received xylitol syrup or gum, and these children required antimicrobials less often than did controls. Xylitol was well tolerated. CONCLUSIONS: Xylitol sugar, when given in a syrup or chewing gum, was effective in preventing AOM and decreasing the need for antimicrobials.

The effects of xylitol and sorbitol on lysozyme- and peroxidase-related enzymatic and candidacidal activities.[Pubmed:25874813]

Arch Oral Biol. 2015 Jul;60(7):998-1006.

OBJECTIVE: To investigate whether xylitol and sorbitol affect enzymatic and candidacidal activities of lysozyme, the peroxidase system, and the glucose oxidase-mediated peroxidase system. DESIGN: Xylitol and sorbitol were added to hen egg-white lysozyme, bovine lactoperoxidase, glucose oxidase-mediated peroxidase, and whole saliva in solution and on hydroxyapatite surfaces. The enzymatic activities of lysozyme, peroxidase, and glucose oxidase-mediated peroxidase were determined by the turbidimetric method, the NbsSCN assay, and production of oxidized o-dianisidine, respectively. Candidacidal activities were determined by comparing colony forming units using Candida albicans ATCC strains 10231, 11006, and 18804. RESULTS: While xylitol and sorbitol did not affect the enzymatic activity of hen egg-white lysozyme both in solution and on hydroxyapatite surfaces, they did inhibit the enzymatic activity of salivary lysozyme significantly in solution, but not on the surfaces. Xylitol and sorbitol enhanced the enzymatic activities of both bovine lactoperoxidase and salivary peroxidase significantly in a dose-dependent manner in solution, but not on the surfaces. Sorbitol, but not xylitol, inhibited the enzymatic activity of glucose oxidase-mediated peroxidase significantly. Both xylitol and sorbitol did not affect candidacidal activities of hen egg-white lysozyme, the bovine lactoperoxidase system, or the glucose oxidase-mediated bovine lactoperoxidase system. CONCLUSIONS: Xylitol and sorbitol inhibited salivary lysozyme activity, but enhanced both bovine lactoperoxidase and salivary peroxidase activities significantly in solution. Xylitol and sorbitol did not augment lysozyme- and peroxidase-related candidacidal activities.

Xylitol, an anticaries agent, exhibits potent inhibition of inflammatory responses in human THP-1-derived macrophages infected with Porphyromonas gingivalis.[Pubmed:24592909]

J Periodontol. 2014 Jun;85(6):e212-23.

BACKGROUND: Xylitol is a well-known anticaries agent and has been used for the prevention and treatment of dental caries. In this study, the anti-inflammatory effects of xylitol are evaluated for possible use in the prevention and treatment of periodontal infections. METHODS: Cytokine expression was stimulated in THP-1 (human monocyte cell line)-derived macrophages by live Porphyromonas gingivalis, and enzyme-linked immunosorbent assay and a commercial multiplex assay kit were used to determine the effects of xylitol on live P. gingivalis-induced production of cytokine. The effects of xylitol on phagocytosis and the production of nitric oxide were determined using phagocytosis assay, viable cell count, and Griess reagent. The effects of xylitol on P. gingivalis adhesion were determined by immunostaining, and costimulatory molecule expression was examined by flow cytometry. RESULTS: Live P. gingivalis infection increased the production of representative proinflammatory cytokines, such as tumor necrosis factor-alpha and interleukin (IL)-1beta, in a multiplicity of infection- and time-dependent manner. Live P. gingivalis also enhanced the release of cytokines and chemokines, such as IL-12 p40, eotaxin, interferon gamma-induced protein 10, monocyte chemotactic protein-1, and macrophage inflammatory protein-1. The pretreatment of xylitol significantly inhibited the P. gingivalis-induced cytokines production and nitric oxide production. In addition, xylitol inhibited the attachment of live P. gingivalis on THP-1-derived macrophages. Furthermore, xylitol exerted antiphagocytic activity against both Escherichia coli and P. gingivalis. CONCLUSION: These findings suggest that xylitol acts as an anti-inflammatory agent in THP-1-derived macrophages infected with live P. gingivalis, which supports its use in periodontitis.

Description

It is a chemical categorized as a polyalcohol or sugar alcohol.

Keywords:

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