Tannic acid

CAS# 1401-55-4

Tannic acid

2D Structure

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3D structure

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Tannic acid

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Chemical Properties of Tannic acid

Cas No. 1401-55-4 SDF Download SDF
PubChem ID 16129878 Appearance Powder
Formula C76H52O46 M.Wt 1701.2
Type of Compound Phenols Storage Desiccate at -20°C
Solubility DMSO : 100 mg/mL (58.78 mM; Need ultrasonic)
H2O : ≥ 100 mg/mL (58.78 mM)
*"≥" means soluble, but saturation unknown.
SMILES C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)OCC3C(C(C(C(O3)OC(=O)C4=CC(=C(C(=C4)OC(=O)C5=CC(=C(C(=C5)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)OC(=O)C9=CC(=C(C(=C9)O)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)OC(=O)C1=CC(=C(C(=C1)O)O)O)O)O
Standard InChIKey LRBQNJMCXXYXIU-UHFFFAOYSA-N
Standard InChI InChI=1S/C76H52O46/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26/h1-20,52,63-65,76-101H,21H2
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 Tannic acid

The peel of Punica granatum L.

Biological Activity of Tannic acid

DescriptionTannic acid has potential in the prevention of obesity.Tannic acid modifies silver nanoparticles are good candidates for microbicides used in treatment of herpesvirus infections.Tannic acid is directly harmful to larvae in a dose- and time-dependent manner and modulates immune responses of sheep WBC stimulated by H. contortus antigen by inhibiting Th1 cytokines and increasing Th2 cytokine expression in vitro.
TargetsIL Receptor | ROS | Fatty Acid Synthase | PPAR | HSV | NADPH-oxidase | IFN-c | TNF-α
In vitro

Effects of tannic acid on Haemonchus contortus larvae viability and immune responses of sheep white blood cells in vitro.[Pubmed: 24558656]

Parasite Immunol. 2014 Feb;36(2):100-6.


METHODS AND RESULTS:
Direct inhibitory effects of Tannic acid on Haemonchus contortus viability were studied in vitro using the larval migration inhibition (LMI) assay. Sheep white blood cells (WBC) were preincubated with 5 and 50 lg/mL Tannic acid or not followed by whole H. contortus antigen (WHA). Cells were harvested at 24 h post-incubation to test host immune responses. Concentrations of 50, 100, 500, 1000, 3000 and 5000 lg/mL Tannic acid inhibited larvae migration by 19.8, 42.4, 46.3, 92.0, 93.7 and 100%, respectively, within 96 h post-incubation (P < 0.001). The relative mRNA levels of interferon (IFN)-c, interleukin (IL)-2, IL-4 and IL-10 were increased by WHA stimulation without Tannic acid. However, the increased effects on IFN-c and IL-2 were inhibited by Tannic acid preincubation (P < 0.001), while the increases in IL-4 and IL-10 were greatly enhanced by Tannic acid preincubation (P < 0.001). Changes in protein levels of all cytokines essentially paralleled the changes in their corresponding mRNA levels.
CONCLUSIONS:
In conclusion, Tannic acid is directly harmful to larvae in a dose- and time-dependent manner and modulates immune responses of sheep WBC stimulated by H. contortus antigen by inhibiting Th1 cytokines and increasing Th2 cytokine expression in vitro.

Effect of calcium, tannic acid, phytic acid and pectin over iron uptake in an in vitro Caco-2 cell model.[Pubmed: 24531910]

Biol Trace Elem Res. 2014 Apr;158(1):122-7.

Calcium, phytic acid, polyphenols and fiber are major inhibitors of iron absorption and they could be found in excess in some diets, thereby altering or modifying the iron nutrition status. The purpose of this study is to evaluate the effect of calcium, Tannic acid, phytic acid, and pectin over iron uptake, using an in vitro model of epithelial cells (Caco-2 cell line).
METHODS AND RESULTS:
Caco-2 cells were incubated with iron (10-30 μM) with or without CaCl2 (500 and 1,000 μM) for 24 h. Then, cells were challenged with phytic acid (50-150 μM); pectin (50-150 nM) or Tannic acid (100-500 μM) for another 24 h. Finally, (55)Fe (10 μM) uptake was determined. Iron dialyzability was studied using an in vitro digestion method. Iron uptake in cells pre-incubated with 20 and 30 μM Fe was inhibited by CaCl2 (500 μM). Iron uptake decreased in cells cultured with Tannic acid (300 μM) and CaCl2 (500-1,000 μM) (two-way ANOVA, p = 0.002). Phytic acid also decreased iron uptake mainly when cells were treated with CaCl2 (1,000 μM) (two-way ANOVA; p < 0.05). Pectin slightly decreased iron uptake (p = NS). Iron dialyzability decreased when iron was mixed with CaCl2 and phytic or Tannic acid (T test p < 0.0001, for both) but not when mixed with pectin.
CONCLUSIONS:
Phytic acid combined with calcium is a strong iron uptake inhibitor. Pectin slightly decreased iron uptake with or without calcium. Tannic acid showed an unexpected behavior, inducing an increase on iron uptake, despite its low Fe dialyzability.

Tannic acid modified silver nanoparticles show antiviral activity in herpes simplex virus type 2 infection.[Pubmed: 25117537]

PLoS One. 2014 Aug 12;9(8):e104113.

The interaction between silver nanoparticles and herpesviruses is attracting great interest due to their antiviral activity and possibility to use as microbicides for oral and anogenital herpes.
METHODS AND RESULTS:
In this work, we demonstrate that Tannic acid modified silver nanoparticles sized 13 nm, 33 nm and 46 nm are capable of reducing HSV-2 infectivity both in vitro and in vivo. The antiviral activity of Tannic acid modified silver nanoparticles was size-related, required direct interaction and blocked virus attachment, penetration and further spread. All tested Tannic acid modified silver nanoparticles reduced both infection and inflammatory reaction in the mouse model of HSV-2 infection when used at infection or for a post-infection treatment. Smaller-sized nanoparticles induced production of cytokines and chemokines important for anti-viral response. The corresponding control buffers with Tannic acid showed inferior antiviral effects in vitro and were ineffective in blocking in vivo infection.
CONCLUSIONS:
Our results show that Tannic acid modified silver nanoparticles are good candidates for microbicides used in treatment of herpesvirus infections.

Protocol of Tannic acid

Kinase Assay

Inhibitory effects of tannic acid on fatty acid synthase and 3T3-L1 preadipocyte.[Pubmed: 24046866]

Biochim Biophys Acta. 2013 Jul;1831(7):1260-6.

Tannic acid is a hydrolyzable tannin that exists in many widespread edible plants with a variety of biological activities.
METHODS AND RESULTS:
In this study, we found that Tannic acid potently inhibited the activity of fatty acid synthase (FAS) in a concentration-dependent manner with a half-inhibitory concentration value (IC50) of 0.14 microM. The inhibition kinetic results showed that the inhibition of FAS by Tannic acid was mixed competitive and noncompetitive manner with respect to acetyl-CoA and malonyl-CoA, but uncompetitive to NADPH. Tannic acid prevented the differentiation of 3T3-L1 pre-adipocytes, and thus repressed intracellular lipid accumulation. In the meantime, Tannic acid decreased the expression of FAS and down-regulated the mRNA level of FAS and PPARgamma during adipocyte differentiation. Further studies showed that the inhibitory effect of Tannic acid did not relate to FAS non-specific sedimentation.
CONCLUSIONS:
Since FAS was believed to be a therapeutic target of obesity, these findings suggested that Tannic acid was considered having potential in the prevention of obesity.

Cell Research

Assessment of in vitro cellular responses of monocytes and keratinocytes to tannic acid modified silver nanoparticles.[Pubmed: 23727252]

Toxicol In Vitro. 2013 Sep;27(6):1798-808.

Hydrolyzable tannins are known to exhibit diverse biological effects, which can be used in combination with silver nanoparticles (AgNPs).
METHODS AND RESULTS:
In this study, we tested toxic and inflammatory properties of tannic-acid modified 13, 33, 46 nm and unmodified 10-65 nm AgNPs using murine 291.03C keratinocyte and RAW 264.7 monocyte cell lines. Both cell lines exposed for 24h to 1-10 μg/ml of 13 nm, 33 nm, 46 nm and unmodified AgNPs showed dose-dependent toxicity and decreased cell proliferation. Only small-sized AgNPs induced production of ROS by monocytes, but not keratinocytes. Monocytes internalized large aggregates of 33, 46 nm and 10-65 nm AgNPs in cytoplasmic vacuoles, whereas keratinocytes accumulated less particles. AgNPs of 13 nm were localized ubiquitously within both cell types. The tested AgNPs strongly down-regulated production of tumor necrosis factor-α (TNF-α) by monocytes, whereas keratinocytes exposed to AgNPs showed an opposite effect. Unmodified but not Tannic acid-modified AgNPs increased production of the pro-inflammatory MCP-1 by monocytes and keratinocytes.
CONCLUSIONS:
In summary, low inflammatory potential and lack of ROS production by tannic-acid modified AgNPs sized above 30 nm suggests that Tannic acid modification of large silver nanoparticles may help to increase AgNPs biosafety.

Tannic acid Dilution Calculator

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Tannic acid Molarity Calculator

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Preparing Stock Solutions of Tannic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.5878 mL 2.9391 mL 5.8782 mL 11.7564 mL 14.6955 mL
5 mM 0.1176 mL 0.5878 mL 1.1756 mL 2.3513 mL 2.9391 mL
10 mM 0.0588 mL 0.2939 mL 0.5878 mL 1.1756 mL 1.4696 mL
50 mM 0.0118 mL 0.0588 mL 0.1176 mL 0.2351 mL 0.2939 mL
100 mM 0.0059 mL 0.0294 mL 0.0588 mL 0.1176 mL 0.147 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 Tannic acid

Assessment of in vitro cellular responses of monocytes and keratinocytes to tannic acid modified silver nanoparticles.[Pubmed:23727252]

Toxicol In Vitro. 2013 Sep;27(6):1798-808.

Hydrolyzable tannins are known to exhibit diverse biological effects, which can be used in combination with silver nanoparticles (AgNPs). In this study, we tested toxic and inflammatory properties of tannic-acid modified 13, 33, 46 nm and unmodified 10-65 nm AgNPs using murine 291.03C keratinocyte and RAW 264.7 monocyte cell lines. Both cell lines exposed for 24h to 1-10 mug/ml of 13 nm, 33 nm, 46 nm and unmodified AgNPs showed dose-dependent toxicity and decreased cell proliferation. Only small-sized AgNPs induced production of ROS by monocytes, but not keratinocytes. Monocytes internalized large aggregates of 33, 46 nm and 10-65 nm AgNPs in cytoplasmic vacuoles, whereas keratinocytes accumulated less particles. AgNPs of 13 nm were localized ubiquitously within both cell types. The tested AgNPs strongly down-regulated production of tumor necrosis factor-alpha (TNF-alpha) by monocytes, whereas keratinocytes exposed to AgNPs showed an opposite effect. Unmodified but not Tannic acid-modified AgNPs increased production of the pro-inflammatory MCP-1 by monocytes and keratinocytes. In summary, low inflammatory potential and lack of ROS production by tannic-acid modified AgNPs sized above 30 nm suggests that Tannic acid modification of large silver nanoparticles may help to increase AgNPs biosafety.

Inhibitory effects of tannic acid on fatty acid synthase and 3T3-L1 preadipocyte.[Pubmed:24046866]

Biochim Biophys Acta. 2013 Jul;1831(7):1260-6.

Tannic acid is a hydrolyzable tannin that exists in many widespread edible plants with a variety of biological activities. In this study, we found that Tannic acid potently inhibited the activity of fatty acid synthase (FAS) in a concentration-dependent manner with a half-inhibitory concentration value (IC50) of 0.14 microM. The inhibition kinetic results showed that the inhibition of FAS by Tannic acid was mixed competitive and noncompetitive manner with respect to acetyl-CoA and malonyl-CoA, but uncompetitive to NADPH. Tannic acid prevented the differentiation of 3T3-L1 pre-adipocytes, and thus repressed intracellular lipid accumulation. In the meantime, Tannic acid decreased the expression of FAS and down-regulated the mRNA level of FAS and PPARgamma during adipocyte differentiation. Further studies showed that the inhibitory effect of Tannic acid did not relate to FAS non-specific sedimentation. Since FAS was believed to be a therapeutic target of obesity, these findings suggested that Tannic acid was considered having potential in the prevention of obesity.

Effect of calcium, tannic acid, phytic acid and pectin over iron uptake in an in vitro Caco-2 cell model.[Pubmed:24531910]

Biol Trace Elem Res. 2014 Apr;158(1):122-7.

Calcium, phytic acid, polyphenols and fiber are major inhibitors of iron absorption and they could be found in excess in some diets, thereby altering or modifying the iron nutrition status. The purpose of this study is to evaluate the effect of calcium, Tannic acid, phytic acid, and pectin over iron uptake, using an in vitro model of epithelial cells (Caco-2 cell line). Caco-2 cells were incubated with iron (10-30 muM) with or without CaCl2 (500 and 1,000 muM) for 24 h. Then, cells were challenged with phytic acid (50-150 muM); pectin (50-150 nM) or Tannic acid (100-500 muM) for another 24 h. Finally, (55)Fe (10 muM) uptake was determined. Iron dialyzability was studied using an in vitro digestion method. Iron uptake in cells pre-incubated with 20 and 30 muM Fe was inhibited by CaCl2 (500 muM). Iron uptake decreased in cells cultured with Tannic acid (300 muM) and CaCl2 (500-1,000 muM) (two-way ANOVA, p = 0.002). Phytic acid also decreased iron uptake mainly when cells were treated with CaCl2 (1,000 muM) (two-way ANOVA; p < 0.05). Pectin slightly decreased iron uptake (p = NS). Iron dialyzability decreased when iron was mixed with CaCl2 and phytic or Tannic acid (T test p < 0.0001, for both) but not when mixed with pectin. Phytic acid combined with calcium is a strong iron uptake inhibitor. Pectin slightly decreased iron uptake with or without calcium. Tannic acid showed an unexpected behavior, inducing an increase on iron uptake, despite its low Fe dialyzability.

Tannic acid modified silver nanoparticles show antiviral activity in herpes simplex virus type 2 infection.[Pubmed:25117537]

PLoS One. 2014 Aug 12;9(8):e104113.

The interaction between silver nanoparticles and herpesviruses is attracting great interest due to their antiviral activity and possibility to use as microbicides for oral and anogenital herpes. In this work, we demonstrate that Tannic acid modified silver nanoparticles sized 13 nm, 33 nm and 46 nm are capable of reducing HSV-2 infectivity both in vitro and in vivo. The antiviral activity of Tannic acid modified silver nanoparticles was size-related, required direct interaction and blocked virus attachment, penetration and further spread. All tested Tannic acid modified silver nanoparticles reduced both infection and inflammatory reaction in the mouse model of HSV-2 infection when used at infection or for a post-infection treatment. Smaller-sized nanoparticles induced production of cytokines and chemokines important for anti-viral response. The corresponding control buffers with Tannic acid showed inferior antiviral effects in vitro and were ineffective in blocking in vivo infection. Our results show that Tannic acid modified silver nanoparticles are good candidates for microbicides used in treatment of herpesvirus infections.

Effects of tannic acid on Haemonchus contortus larvae viability and immune responses of sheep white blood cells in vitro.[Pubmed:24558656]

Parasite Immunol. 2014 Feb;36(2):100-6.

Direct inhibitory effects of Tannic acid on Haemonchus contortus viability were studied in vitro using the larval migration inhibition (LMI) assay. Sheep white blood cells (WBC) were preincubated with 5 and 50 lg/mL Tannic acid or not followed by whole H. contortus antigen (WHA). Cells were harvested at 24 h post-incubation to test host immune responses. Concentrations of 50, 100, 500, 1000, 3000 and 5000 lg/mL Tannic acid inhibited larvae migration by 19.8, 42.4, 46.3, 92.0, 93.7 and 100%, respectively, within 96 h post-incubation (P < 0.001). The relative mRNA levels of interferon (IFN)-c, interleukin (IL)-2, IL-4 and IL-10 were increased by WHA stimulation without Tannic acid. However, the increased effects on IFN-c and IL-2 were inhibited by Tannic acid preincubation (P < 0.001), while the increases in IL-4 and IL-10 were greatly enhanced by Tannic acid preincubation (P < 0.001). Changes in protein levels of all cytokines essentially paralleled the changes in their corresponding mRNA levels. In conclusion, Tannic acid is directly harmful to larvae in a dose- and time-dependent manner and modulates immune responses of sheep WBC stimulated by H. contortus antigen by inhibiting Th1 cytokines and increasing Th2 cytokine expression in vitro.

Description

Tannic acid is a novel hERG channel blocker with IC50 of 3.4 μM.

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