Phytic acid

CAS# 83-86-3

Phytic acid

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Quality Control of Phytic acid

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Chemical structure

Phytic acid

3D structure

Chemical Properties of Phytic acid

Cas No. 83-86-3 SDF Download SDF
PubChem ID 890 Appearance Powder
Formula C6H18O24P6 M.Wt 660.04
Type of Compound Miscellaneous Storage Desiccate at -20°C
Synonyms myo-Inositol, hexakis(dihydrogen phosphate); Inositol hexaphosphate
Solubility H2O : ≥ 30 mg/mL (45.45 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (2,3,4,5,6-pentaphosphonooxycyclohexyl) dihydrogen phosphate
SMILES C1(C(C(C(C(C1OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O
Standard InChIKey IMQLKJBTEOYOSI-UHFFFAOYSA-N
Standard InChI InChI=1S/C6H18O24P6/c7-31(8,9)25-1-2(26-32(10,11)12)4(28-34(16,17)18)6(30-36(22,23)24)5(29-35(19,20)21)3(1)27-33(13,14)15/h1-6H,(H2,7,8,9)(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)(H2,19,20,21)(H2,22,23,24)
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 Phytic acid

The herbs of Oryza sativa

Biological Activity of Phytic acid

DescriptionPhytic acid is the principal storage form of phosphorus in many plant tissues, especially bran and seeds. It can act as a cofactor in DNA repair by nonhomologous end-joining. It is a trypsin inhibitor, has chelating, antioxidant, anti-inflammatory, and neuroprotective effects, it forms an iron chelate which greatly accelerates Fe2+-mediated oxygen reduction yet blocks iron-driven hydroxyl radical generation and suppresses lipid peroxidation. High concentrations of phytic acid prevent browning and putrefaction of various fruits and vegetables by inhibiting polyphenol oxidase, it may be a substitute for presently employed preservatives.
TargetsNF-kB | ERK | NOS | Antifection
In vitro

Effect of phytic acid etchant on the structural stability of demineralized dentine and dentine bonding.[Pubmed: 25933170]

J Mech Behav Biomed Mater. 2015 Apr 6;48:145-152.

This study examined the effect of Phytic acid (IP6) in stabilizing the morphology of dentine collagen network and resin-dentine bonding.
METHODS AND RESULTS:
Dentine beams were fully demineralized with 10% phosphoric acid (PA) or 1% IP6 (pH 1.2). PA-demineralized beams were divided into three groups: (a) no further treatment (control), (b) treatment with 5% glutaraldehyde (GA) for 1 h and (c) treatment with 1% IP6 (pH 7) for 1 h. IP6-demineralized beams received no further treatment. The beams were then subjected to ultimate tensile strength (UTS) testing. Dentine micromorphology evaluation was performed using a field-emission scanning electron microscope (FE-SEM). Dentine disks were etched with 35% PA for 15 s or 1% IP6 for 30s. PA-etched dentine disks were divided into three groups as (a), (b) and (c) as for UTS testing, but the treatment with GA or IP6 was done in 1min. For microtensile bond strength (μTBS) testing, flat dentine surfaces etched with PA or IP6 were blot-dried (wet dentine) or air-dried for 10s (dry dentine) and bonded with an etch-and-rinse adhesive followed by composite build-up. IP6-demineralized dentine showed significantly higher UTS, when compared to PA-demineralized dentine. GA and IP6 significantly improved UTS of PA-demineralized dentine. FE-SEM observation revealed that dentine collagen network was preserved by GA and IP6. No significant difference in μTBS was found between the wet and dry IP6-etched dentine groups.
CONCLUSIONS:
IP6 etching showed a structural stabilizing effect on demineralized dentine matrix and produced good resin-dentine bonding, regardless of dentine moistness or dryness.

A carbon dot-based [Pubmed: 25829220]

Biosens Bioelectron. 2015 Mar 20;70:232-238.


METHODS AND RESULTS:
We herein report a facile, one-step pyrolysis synthesis of photoluminescent carbon dots (CDs) using citric acid as the carbon source and lysine as the surface passivation reagent. The as-prepared CDs show narrow size distribution, excellent blue fluorescence and good photo-stability and water dispersivity. The fluorescence of the CDs was found to be effectively quenched by ferric (Fe(III)) ions with high selectivity via a photo-induced electron transfer (PET) process. Upon addition of Phytic acid (PA) to the CDs/Fe(III) complex dispersion, the fluorescence of the CDs was significantly recovered, arising from the release of Fe(III) ions from the CDs/Fe(III) complex because PA has a higher affinity for Fe(III) ions compared to CDs. Furthermore, we developed an "off-on" fluorescence assay method for the detection of Phytic acid using CDs/Fe(III) as a fluorescent probe. This probe enables the selective detection of PA with a linear range of 0.68-18.69 μM and a limit of detection (signal-to-noise ratio is 3) of 0.36 μM.
CONCLUSIONS:
The assay method demonstrates high selectivity, repeatability, stability and recovery ratio in the detection of the standard and real PA samples. We believe that the facile operation, low-cost, high sensitivity and selectivity render this CD-based "off-on" fluorescent probe an ideal sensing platform for the detection of PA.

Phytic acid. A natural antioxidant.[Reference: WebLink]

J. Biol. Chem., 1987, 262(24):11647-50.


METHODS AND RESULTS:
The catalysis by iron of radical formation and subsequent oxidative damage has been well documented. Although many iron-chelating agents potentiate reactive oxygen formation and lipid peroxidation, Phytic acid (abundant in edible legumes, cereals, and seeds) forms an iron chelate which greatly accelerates Fe2+-mediated oxygen reduction yet blocks iron-driven hydroxyl radical generation and suppresses lipid peroxidation. Furthermore, high concentrations of Phytic acid prevent browning and putrefaction of various fruits and vegetables by inhibiting polyphenol oxidase.
CONCLUSIONS:
These observations indicate an important antioxidant function for phytate in seeds during dormancy and suggest that phytate may be a substitute for presently employed preservatives, many of which pose potential health hazards.

In vivo

Phytic acid attenuates inflammatory responses and the levels of NF-κB and p-ERK in MPTP-induced Parkinson's disease model of mice.[Pubmed: 25929185]

Neurosci Lett. 2015 Apr 27;597:132-136.

Phytic acid (PA) is a naturally occurring constituent which exhibits protective action in Parkinson's disease (PD). Inflammation in the central nervous system (CNS) is strongly associated with neuronal death in PD. However, the molecular mechanism of the protective effect of Phytic acid in PD has not been fully elucidated.
METHODS AND RESULTS:
In this study, we tried to testify the protection of Phytic acid on neuron and inflammatory responses in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced PD model of mice and investigated the mechanism involved in them. Motor behavior test and tyrosine hydroxylase (TH) immunohistochemistry method showed Phytic acid significantly inhibited MPTP-induced dopaminergic cell loss in the substantia nigra (SN). Moreover, using immunohistochemistry method and quantitative polymerase chain reaction (qPCR), microglial activation and inducible nitric oxide synthase (iNOS) were found to be markedly repressed by Phytic acid . Via western blot assay, expressions of nuclear factor κB (NF-κB) and phosphorylated extracellular signal-regulated kinase (p-ERK) were significantly attenuated by Phytic acid .
CONCLUSIONS:
In conclusion, it is suggested that Phytic acid has a neuroprotective effect in MPTP-induced PD model and the neuroprotection is correlated with its anti-inflammatory effect which may be associated with suppression of pathways that involved in NF-κB and p-ERK.

Protocol of Phytic acid

Structure Identification
J Nutr. 1995 Mar;125(3 Suppl):581S-588S.

Compositional changes in trypsin inhibitors, phytic acid, saponins and isoflavones related to soybean processing.[Pubmed: 7884537]


METHODS AND RESULTS:
We herein report a facile, one-step pyrolysis synthesis of photoluminescent carbon dots (CDs) using citric acid as the carbon source and lysine as the surface passivation reagent. The as-prepared CDs show narrow size distribution, excellent blue fluorescence and good photo-stability and water dispersivity. The fluorescence of the CDs was found to be effectively quenched by ferric (Fe(III)) ions with high selectivity via a photo-induced electron transfer (PET) process. Upon addition of Phytic acid (PA) to the CDs/Fe(III) complex dispersion, the fluorescence of the CDs was significantly recovered, arising from the release of Fe(III) ions from the CDs/Fe(III) complex because PA has a higher affinity for Fe(III) ions compared to CDs. Furthermore, we developed an "off-on" fluorescence assay method for the detection of Phytic acid using CDs/Fe(III) as a fluorescent probe. This probe enables the selective detection of PA with a linear range of 0.68-18.69 μM and a limit of detection (signal-to-noise ratio is 3) of 0.36 μM.
CONCLUSIONS:
The assay method demonstrates high selectivity, repeatability, stability and recovery ratio in the detection of the standard and real PA samples. We believe that the facile operation, low-cost, high sensitivity and selectivity render this CD-based "off-on" fluorescent probe an ideal sensing platform for the detection of PA.

Phytic acid Dilution Calculator

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Preparing Stock Solutions of Phytic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.5151 mL 7.5753 mL 15.1506 mL 30.3012 mL 37.8765 mL
5 mM 0.303 mL 1.5151 mL 3.0301 mL 6.0602 mL 7.5753 mL
10 mM 0.1515 mL 0.7575 mL 1.5151 mL 3.0301 mL 3.7876 mL
50 mM 0.0303 mL 0.1515 mL 0.303 mL 0.606 mL 0.7575 mL
100 mM 0.0152 mL 0.0758 mL 0.1515 mL 0.303 mL 0.3788 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 Phytic acid

Phytic acid is a major phosphorus storage compound of most seeds and cereal grains.

In Vitro:Phytic acid, a major phosphorus storage compound of most seeds and cereal grains, contributes about 1 to 7% of their dry weight. It may account for more than 70% of the total kernel phosphorus. Phytic acid has the strong ability to chelate multivalent metal ions, especially zinc, calcium, and iron. The binding can result in very insoluble salts that are poorly absorbed from the gastrointestinal tract, which results in poor bioavailability of minerals. Phytic acid is also considered to be a natural antioxidant and is suggested to have potential functions of reducing lipid peroxidation and as a preservative in foods[1]. Phytic acid inhibits the formation of uric acid from xanthine with an IC50 of about 30 mM. The generation of the superoxide is greatly affected by phytic acid; the IC50 is about 6 mM, indicating that the superoxide generating domain of XO is more sensitive to phytic acid[2]. There has been observed an inhibition of tumor growth and induction of cell differentiation in the presence of phytic acid in a few cancer cell lines including colon, nipple, breast, prostate, cervix, liver, pancreas, melanoma and glioblastoma[3].

In Vivo:Phytic acid has a neuroprotective effect in MPTP-induced PD model and the neuroprotection is correlated with its anti-inflammatory effect which may be associated with suppression of pathways that involved in NF-κB and p-ERK. Phytic acid significantly inhibits MPTP-induced dopaminergic cell loss in the substantia nigra (SN). Moreover, using immunohistochemistry method and quantitative polymerase chain reaction (qPCR), microglial activation and inducible nitric oxide synthase (iNOS) are found to be markedly repressed by phytic acid[4].

References:
[1]. Zhou JR, et al. Phytic acid in health and disease. Crit Rev Food Sci Nutr. 1995 Nov;35(6):495-508. [2]. Muraoka S, et al. Inhibition of xanthine oxidase by phytic acid and its antioxidative action. Life Sci. 2004 Feb 13;74(13):1691-700. [3]. Nawrocka-Musial D, et al. Phytic acid--anticancer nutriceutic. Pol Merkur Lekarski. 2012 Jul;33(193):43-7. [4]. Lv Y, et al. Phytic acid attenuates inflammatory responses and the levels of NF-κB and p-ERK in MPTP-induced Parkinson's disease model of mice. Neurosci Lett. 2015 Jun 15;597:132-6.

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References on Phytic acid

Compositional changes in trypsin inhibitors, phytic acid, saponins and isoflavones related to soybean processing.[Pubmed:7884537]

J Nutr. 1995 Mar;125(3 Suppl):581S-588S.

Soybeans are high in protein but also contain a number of minor constituents traditionally considered to be antinutritional factors. These include trypsin inhibitors, Phytic acid, saponins and isoflavones. These compounds are now thought to have beneficial biological effects in the diet, such as lowering blood cholesterol or preventing cancer. Soybean processing changes the content of these minor constituents in various ways. This review discusses the changes in content of trypsin inhibitors, Phytic acid, saponins and isoflavones as soybeans are processed into the conventional protein ingredients, flours, concentrates and isolates, as well as some of the traditional Oriental soybean foods.

Repeat length variation in the 5'UTR of myo-inositol monophosphatase gene is related to phytic acid content and contributes to drought tolerance in chickpea (Cicer arietinum L.).[Pubmed:25888598]

J Exp Bot. 2015 Sep;66(19):5683-90.

Myo-inositol metabolism plays a significant role in plant growth and development, and is also used as a precursor for many important metabolites, such as ascorbate, pinitol, and phytate. Phytate (inositol hexakisphosphate) is the major storage pool for phosphate in the seeds. It is utilized during seed germination and growth of the developing embryo. In addition, it is implicated in protection against oxidative stress. In the present study, a panel of chickpea accessions was used for an association analysis. Association analysis accounting for population structure and relative kinship identified alleles of a simple sequence repeat marker, NCPGR90, that are associated with both Phytic acid content and drought tolerance. These alleles varied with respect to the dinucleotide CT repeats present within the marker. NCPGR90 located to the 5'UTR of chickpea myo-inositol monophosphatase gene (CaIMP) and showed transcript length variation in drought-tolerant and drought-susceptible accessions. CaIMP from a drought-tolerant accession with a smaller repeat was almost 2-fold upregulated as compared to a susceptible accession having a longer repeat, even under control non-stressed conditions. This study suggests an evolution of simple sequence repeat length variation in CaIMP, which might be regulating Phytic acid levels to confer drought tolerance in natural populations of chickpea.

A carbon dot-based "off-on" fluorescent probe for highly selective and sensitive detection of phytic acid.[Pubmed:25829220]

Biosens Bioelectron. 2015 Aug 15;70:232-8.

We herein report a facile, one-step pyrolysis synthesis of photoluminescent carbon dots (CDs) using citric acid as the carbon source and lysine as the surface passivation reagent. The as-prepared CDs show narrow size distribution, excellent blue fluorescence and good photo-stability and water dispersivity. The fluorescence of the CDs was found to be effectively quenched by ferric (Fe(III)) ions with high selectivity via a photo-induced electron transfer (PET) process. Upon addition of Phytic acid (PA) to the CDs/Fe(III) complex dispersion, the fluorescence of the CDs was significantly recovered, arising from the release of Fe(III) ions from the CDs/Fe(III) complex because PA has a higher affinity for Fe(III) ions compared to CDs. Furthermore, we developed an "off-on" fluorescence assay method for the detection of Phytic acid using CDs/Fe(III) as a fluorescent probe. This probe enables the selective detection of PA with a linear range of 0.68-18.69 muM and a limit of detection (signal-to-noise ratio is 3) of 0.36 muM. The assay method demonstrates high selectivity, repeatability, stability and recovery ratio in the detection of the standard and real PA samples. We believe that the facile operation, low-cost, high sensitivity and selectivity render this CD-based "off-on" fluorescent probe an ideal sensing platform for the detection of PA.

Phytic acid attenuates inflammatory responses and the levels of NF-kappaB and p-ERK in MPTP-induced Parkinson's disease model of mice.[Pubmed:25929185]

Neurosci Lett. 2015 Jun 15;597:132-6.

Phytic acid (PA) is a naturally occurring constituent which exhibits protective action in Parkinson's disease (PD). Inflammation in the central nervous system (CNS) is strongly associated with neuronal death in PD. However, the molecular mechanism of the protective effect of PA in PD has not been fully elucidated. In this study, we tried to testify the protection of PA on neuron and inflammatory responses in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced PD model of mice and investigated the mechanism involved in them. Motor behavior test and tyrosine hydroxylase (TH) immunohistochemistry method showed PA significantly inhibited MPTP-induced dopaminergic cell loss in the substantia nigra (SN). Moreover, using immunohistochemistry method and quantitative polymerase chain reaction (qPCR), microglial activation and inducible nitric oxide synthase (iNOS) were found to be markedly repressed by PA. Via western blot assay, expressions of nuclear factor kappaB (NF-kappaB) and phosphorylated extracellular signal-regulated kinase (p-ERK) were significantly attenuated by PA. In conclusion, it is suggested that PA has a neuroprotective effect in MPTP-induced PD model and the neuroprotection is correlated with its anti-inflammatory effect which may be associated with suppression of pathways that involved in NF-kappaB and p-ERK.

Effect of phytic acid etchant on the structural stability of demineralized dentine and dentine bonding.[Pubmed:25933170]

J Mech Behav Biomed Mater. 2015 Aug;48:145-152.

OBJECTIVE: This study examined the effect of Phytic acid (IP6) in stabilizing the morphology of dentine collagen network and resin-dentine bonding. METHODS: Dentine beams were fully demineralized with 10% phosphoric acid (PA) or 1% IP6 (pH 1.2). PA-demineralized beams were divided into three groups: (a) no further treatment (control), (b) treatment with 5% glutaraldehyde (GA) for 1 h and (c) treatment with 1% IP6 (pH 7) for 1 h. IP6-demineralized beams received no further treatment. The beams were then subjected to ultimate tensile strength (UTS) testing. Dentine micromorphology evaluation was performed using a field-emission scanning electron microscope (FE-SEM). Dentine disks were etched with 35% PA for 15 s or 1% IP6 for 30s. PA-etched dentine disks were divided into three groups as (a), (b) and (c) as for UTS testing, but the treatment with GA or IP6 was done in 1min. For microtensile bond strength (microTBS) testing, flat dentine surfaces etched with PA or IP6 were blot-dried (wet dentine) or air-dried for 10s (dry dentine) and bonded with an etch-and-rinse adhesive followed by composite build-up. RESULTS: IP6-demineralized dentine showed significantly higher UTS, when compared to PA-demineralized dentine. GA and IP6 significantly improved UTS of PA-demineralized dentine. FE-SEM observation revealed that dentine collagen network was preserved by GA and IP6. No significant difference in microTBS was found between the wet and dry IP6-etched dentine groups. CONCLUSION: IP6 etching showed a structural stabilizing effect on demineralized dentine matrix and produced good resin-dentine bonding, regardless of dentine moistness or dryness.

Description

Phytic acid is a phosphorus storage compound of seeds and cereal grains. Phytic acid is known as a food inhibitor, which has a strong ability to chelate multivalent metal ions, specially zinc, calcium, iron and as with protein residue. Phytic acid inhibits the enzymatic superoxide source xanthine oxidase (XO), and has antioxidative, neuroprotective, anti-inflammatory effects.

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