Wikipedia

Phytic acid

"IP6" redirects here. For the Internet Protocol revision, seeIPv6.
"E391" redirects here. For other uses, seeEuropean route E391.

Phytic acidis a six-folddihydrogenphosphateesterofinositol(specifically, of themyoisomer), also calledinositol hexaphosphate,inositol hexakisphosphate(IP6) orinositol polyphosphate.At physiological pH, the phosphates are partially ionized, resulting in thephytateanion.

Phytic acid
Structural formula of phytic acid
Structural formula of phytic acid
Ball-and-stick model of phytic acid
Ball-and-stick model of phytic acid
Carbon,C
Hydrogen,H
Oxygen,O
Phosphorus,P
Space-filling model of phytic acid
Space-filling model of phytic acid
Names
IUPAC name
(1R,2S,3r,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexayl hexakis[dihydrogen (phosphate)]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.369Edit this at Wikidata
E number E391(antioxidants,...)
UNII
  • 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)/t1-,2-,3-,4+,5-,6-checkY
    Key: IMQLKJBTEOYOSI-GPIVLXJGSA-NcheckY
  • InChI=1/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)/t1-,2-,3-,4+,5-,6-
    Key: IMQLKJBTEOYOSI-GPIVLXJGBP
  • [C@@H]1([C@@H]([C@@H]([C@@H]([C@H]([C@@H]1OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O
Properties
C6H18O24P6
Molar mass 660.029g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

The (myo) phytate anion is a colorless species that has significant nutritional role as the principal storage form ofphosphorusin manyplanttissues,especiallybranandseeds.It is also present in manylegumes,cereals, and grains. Phytic acid and phytate have a strong binding affinity to thedietary mineralscalcium,iron,andzinc,inhibiting theirabsorptionin the small intestine.[1]

The lower inositol polyphosphates are inositol esters with less than six phosphates, such as inositol penta- (IP5), tetra- (IP4), and triphosphate (IP3). These occur in nature ascatabolitesof phytic acid.

Significance in agriculture

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The hexavalent phytate anion.

Phytic acid was discovered in 1903.[2]

Generally, phosphorus and inositol in phytate form are notbioavailableto non-ruminantanimals because these animals lack theenzymephytaserequired to hydrolyze the inositol-phosphate linkages.Ruminantsare able to digest phytate because of the phytase produced byrumenmicroorganisms.[3]

In most commercialagriculture,non-ruminantlivestock,such asswine,fowl,andfish,[4]are fed mainlygrains,such asmaize,legumes,andsoybeans.[5]Because phytate from these grains and beans is unavailable for absorption, the unabsorbed phytate passes through thegastrointestinal tract,elevating the amount of phosphorus in the manure.[3]Excess phosphorus excretion can lead to environmental problems, such aseutrophication.[6]The use ofsproutedgrains may reduce the quantity of phytic acids in feed, with no significant reduction of nutritional value.[7]

Also, viable low-phytic acid mutant lines have been developed in several crop species in which the seeds have drastically reduced levels of phytic acid and concomitant increases in inorganic phosphorus.[8]However, germination problems have reportedly hindered the use of these cultivars thus far. This may be due to phytic acid's critical role in both phosphorus and metal ion storage.[9]Phytate variants also have the potential to be used in soil remediation, to immobilizeuranium,nickel,and other inorganic contaminants.[10]

Biological effects

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Plants

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Although indigestible for many animals as they occur in seeds and grains, phytic acid and its metabolites have several important roles for the seedling plant.

Most notably, phytic acid functions as a phosphorus store, as an energy store, as a source of cations and as a source of myo-inositol (a cell wall precursor). Phytic acid is the principal storage form of phosphorus in plant seeds.[11]

Animals

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In animal cells, myo-inositol polyphosphates are ubiquitous, and phytic acid (myo-inositol hexakisphosphate) is the most abundant, with its concentration ranging from 10 to 100 μM in mammalian cells, depending on cell type and developmental stage. Being not directly absorbed in the gut, phytic acid is not obtained from the animal diet, but must be synthesized inside the cell from phosphate and inositol (which in turn is produced from glucose, usually in the kidneys).[12][13]

In vitro

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The interaction of intracellular phytic acid with specific intracellular proteins has been investigatedin vitro,and these interactions have been found to result in the inhibition or potentiation of the activities of those proteins.[14][15]

Inositol hexaphosphate facilitates the formation of the six-helix bundle and assembly of the immature HIV-1 Gag lattice. IP6 makes ionic contacts with two rings of lysine residues at the centre of the Gag hexamer. Proteolytic cleavage then unmasks an alternative binding site, where IP6 interaction promotes the assembly of the mature capsid lattice. These studies identify IP6 as a naturally occurring small molecule that promotes both assembly and maturation of HIV-1.[16]

Dentistry

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IP6 has potential use in endodontics, adhesive, preventive, and regenerative dentistry, and in improving the characteristics and performance of dental materials.[17][18][19]

Food science

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Phytic acid, mostly as phytate in the form of phytin (i.e. the calcium/magnesium salts of phytate), is found within thehullsand kernels of seeds,[20]includingnuts,grains, and pulses.[1]

In-home food preparation techniques may break down the phytic acid in all of these foods. Simply cooking the food will reduce the phytic acid to some degree. More effective methods are soaking in an acid medium,sprouting,andlactic acid fermentationsuch as insourdoughandpickling.[21]

No detectable phytate (less than 0.02% of wet weight) was observed in vegetables such as scallion and cabbage leaves or in fruits such as apples, oranges, bananas, or pears.[22]

As afood additive,phytic acid is used as thepreservativeE391.[23][24]It is allowed as a food additive in the US (GRAS), the EU, Japan, and China. It offers someantioxidantactivity by binding away iron, and is especially effective in meat. It also inhibitspolyphenol oxidase,the enzyme responsible for apple browning. Basic research also suggests that it may deter the growth of pathogenic bacteria and spoilage mold.[25]

Dry food sources of phytic acid[26][22][27][28][29][30][31][32]
Food Proportion by weight (g/100 g)
Min. Max.
Hulled Hemp Seed[20] 4.5 4.5
Pumpkin seed 4.3 4.3
Linseed 2.15 2.78
Sesame seedsflour 5.36 5.36
Chia seeds 0.96 1.16
Almonds 1.35 3.22
Brazil nuts 1.97 6.34
Coconut 0.36 0.36
Hazelnut 0.65 0.65
Peanut 0.95 1.76
Walnut 0.98 0.98
Maize(corn) 0.75 2.22
Oat 0.42 1.16
Oat meal 0.89 2.40
Brown rice 0.84 0.99
Polished rice 0.14 0.60
Wheat 0.39 1.35
Wheat flour 0.25 1.37
Wheat germ 0.08 1.14
Wholewheat bread 0.43 1.05
Beans, pinto 2.38 2.38
Buckwheat 1.00 1.00
Chickpeas 0.56 0.56
Lentils 0.44 0.50
Soybeans 1.00 2.22
Tofu 1.46 2.90
Soybeverage 1.24 1.24
Soy proteinconcentrate 1.24 2.17
Newpotato 0.18 0.34
Spinach 0.22 NR
Avocado fruit 0.51 0.51
Chestnuts[33] 0.47
Sunflower seeds 1.60
Fresh food sources of phytic acid[28]
Food Proportion by weight (%)
Min. Max.
Taro 0.143 0.195
Cassava 0.114 0.152

Dietary mineral absorption

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Phytic acid has a strong affinity to the dietarytrace elements,calcium,iron,andzinc,inhibiting theirabsorptionfrom the small intestine.[1][34]Phytochemicalssuch aspolyphenolsandtanninsalso influence the binding.[35]When iron and zinc bind to phytic acid, they form insoluble precipitates and are far less absorbable in the intestines.[36][37]

Because phytic acid also can affect the absorption ofiron,"dephytinization should be considered as a major strategy to improve iron nutrition during the weaning period".[38]Dephytinization by exogenousphytaseto phytate-containing food is an approach being investigated to improve nutritional health in populations that are vulnerable to mineral deficiency due to their reliance on phytate-laden food staples.Crop breedingto increase mineral density (biofortification) or reducing phytate content are under preliminary research.[39]

See also

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Wikimedia Commons has media related toPhytic acid.

References

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  1. ^abcSchlemmer, U.; Frølich, W.; Prieto, R. M.; Grases, F. (2009)."Phytate in foods and significance for humans: Food sources, intake, processing, bioavailability, protective role and analysis"(PDF).Molecular Nutrition & Food Research.53(Suppl 2): S330–75.doi:10.1002/mnfr.200900099.PMID19774556.Archived fromthe original(PDF)on 2022-10-02.Retrieved2018-11-11.
  2. ^Mullaney EJ, Ullah, Abul H.J."Phytases: attributes, catalytic mechanisms, and applications"(PDF).United States Department of Agriculture–Agricultural Research Service. Archived fromthe original(PDF)on 2012-11-07.RetrievedMay 18,2012.
  3. ^abKlopfenstein TJ, Angel R, Cromwell G, Erickson GE, Fox DG, Parsons C, Satter LD, Sutton AL, Baker DH (July 2002)."Animal Diet Modification to Decrease the Potential for Nitrogen and Phosphorus Pollution".Council for Agricultural Science and Technology.21.
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  23. ^Functional Food - Improve Health through Adequate Food edited by María Chávarri Hueda, pg. 86
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  26. ^Dephytinisation with Intrinsic Wheat Phytase and Iron Fortification Significantly Increase Iron Absorption from Fonio (Digitaria exilis) Meals in West African Women (2013)
  27. ^Reddy NR, Sathe SK (2001).Food Phytates.Boca Raton: CRC.ISBN978-1-56676-867-2.[page needed]
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  29. ^Macfarlane BJ, Bezwoda WR, Bothwell TH, Baynes RD, Bothwell JE, MacPhail AP, Lamparelli RD, Mayet F (February 1988). "Inhibitory effect of nuts on iron absorption".The American Journal of Clinical Nutrition.47(2):270–4.doi:10.1093/ajcn/47.2.270.PMID3341259.
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  31. ^Arendt EK, Zannini E (2013-04-09)."Chapter 11: Buckwheat".Cereal grains for the food and beverage industries.Woodhead Publishing. p. 388.ISBN978-0-85709-892-4.
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  33. ^Scuhlz M."Paleo Diet Guide: With Recipes in 30 Minutes or Less: Diabetes Heart Disease: Paleo Diet Friendly: Dairy Gluten Nut Soy Free Cookbook".PWPH Publications – via Google Books.
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  37. ^Committee on Food Protection; Food and Nutrition Board; National Research Council (1973)."Phytates".Toxicants Occurring Naturally in Foods.National Academy of Sciences. pp.363–371.ISBN978-0-309-02117-3.
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  39. ^Raboy, Victor (22 January 2020)."Low phytic acid crops: Observations based on four decades of research".Plants.9(2): 140.doi:10.3390/plants9020140.ISSN2223-7747.PMC7076677.PMID31979164.
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