phytic acid
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{{chembox
| Watchedfields = changed
| verifiedrevid = 477163323
| ImageFile1 = Phytic acid.svg
| ImageName1 = Structural formula of phytic acid
| ImageFile2 = Phytic acid molecule ball.png
| ImageName2 = Ball-and-stick model of phytic acid
| ImageCaption2 = {{legend|rgb(64, 64, 64)|Carbon, C}}{{legend|white|Hydrogen, H}}{{legend|red|Oxygen, O}}{{legend|orange|Phosphorus, P}}
| ImageFile3 = Phytic acid molecule spacefill.png
| ImageName3 = Space-filling model of phytic acid
| IUPACName = (1R,2S,3r,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexayl hexakis[dihydrogen (phosphate)]
| Section1 = {{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7IGF0S7R8I
| 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-
| InChIKey = IMQLKJBTEOYOSI-GPIVLXJGBP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IMQLKJBTEOYOSI-GPIVLXJGSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 83-86-3
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=16735966
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17401
| SMILES = [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
| PubChem = 890
}}
| Section2 = {{Chembox Properties
| C = 6 | H = 18 | O = 24 | P = 6
| Density =
| MeltingPt =
| BoilingPt =
}}
}}
Phytic acid is a six-fold dihydrogenphosphate ester of inositol (specifically, of the myo isomer), also called inositol hexaphosphate, inositol hexakisphosphate (IP6) or inositol polyphosphate. At physiological pH, the phosphates are partially ionized, resulting in the phytate anion.
The (myo) phytate anion is a colorless species that has significant nutritional role as the principal storage form of phosphorus in many plant tissues, especially bran and seeds. It is also present in many legumes, cereals, and grains. Phytic acid and phytate have a strong binding affinity to the dietary minerals calcium, iron, and zinc, inhibiting their absorption in the small intestine.{{cite journal|last1=Schlemmer|first1=U.|last2=Frølich|first2=W.|last3=Prieto|first3=R. M.|last4=Grases|first4=F.|year=2009|title=Phytate in foods and significance for humans: Food sources, intake, processing, bioavailability, protective role and analysis|url=https://wiebaktmee.nl/cms/pdf/Schlemmer%20_Mol_Nutr_Food_res_2009_Phytate_in_foods_and_significance_for_humans.pdf|journal=Molecular Nutrition & Food Research|volume=53|issue=Suppl 2|pages=S330–75|doi=10.1002/mnfr.200900099|pmid=19774556|archive-date=2022-10-02|access-date=2018-11-11|archive-url=https://web.archive.org/web/20221002094913/https://wiebaktmee.nl/cms/pdf/Schlemmer%20_Mol_Nutr_Food_res_2009_Phytate_in_foods_and_significance_for_humans.pdf|url-status=dead}}
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 as catabolites of phytic acid.
Significance in agriculture
Generally, phosphorus and inositol in phytate form are not bioavailable to non-ruminant animals because these animals lack the enzyme phytase required to hydrolyze the inositol-phosphate linkages. Ruminants are able to digest phytate because of the phytase produced by rumen microorganisms.{{Cite journal|first1=Terry J. |last1=Klopfenstein |first2=Rosalina |last2=Angel |first3=Gary |last3=Cromwell |first4=Galen E. |last4=Erickson |first5=Danny G. |last5=Fox |first6=Carl |last6=Parsons |first7=Larry D. |last7=Satter |first8=Alan L. |last8=Sutton |first9=David H. |last9=Baker | name-list-style = vanc |date=July 2002 |title=Animal Diet Modification to Decrease the Potential for Nitrogen and Phosphorus Pollution |journal=Council for Agricultural Science and Technology |volume=21 |url=http://digitalcommons.unl.edu/animalscifacpub/518/ }}
In most commercial agriculture, non-ruminant livestock, such as swine, fowl, and fish,{{Cite journal | vauthors = Romarheim OH, Zhang C, Penn M, Liu YJ, Tian LX, Skrede A, Krogdahl Å, Storebakken T |year=2008 |journal=Aquaculture Nutrition|title=Growth and intestinal morphology in cobia (Rachycentron canadum) fed extruded diets with two types of soybean meal partly replacing fish meal |volume=14 |issue=2 |pages=174–180 |doi=10.1111/j.1365-2095.2007.00517.x}} are fed mainly grains, such as maize, legumes, and soybeans.{{Cite journal|last1=Jezierny|first1=D.|last2=Mosenthin|first2=R.|last3=Weiss|first3=E.|date=2010-05-01|title=The use of grain legumes as a protein source in pig nutrition: A review|url=https://www.researchgate.net/publication/248333607|journal=Animal Feed Science and Technology |volume=157|issue=3–4|pages=111–128|doi=10.1016/j.anifeedsci.2010.03.001}} Because phytate from these grains and beans is unavailable for absorption, the unabsorbed phytate passes through the gastrointestinal tract, elevating the amount of phosphorus in the manure. Excess phosphorus excretion can lead to environmental problems, such as eutrophication.{{Cite journal | doi = 10.1023/A:1023690824045 |jstor=27503850| year = 2003 |title=Industrialized Animal Production—A Major Source of Nutrient and Microbial Pollution to Aquatic Ecosystems| vauthors = Mallin MA | journal = Population and Environment| volume = 24| issue = 5| pages = 369–385|s2cid=154321894}} The use of sprouted grains may reduce the quantity of phytic acids in feed, with no significant reduction of nutritional value.{{Cite journal|doi=10.1007/BF01092036 |title=Nutritive value of malted millet flours |year=1986 |last1=Malleshi |first1=N. G. |journal=Plant Foods for Human Nutrition |volume=36 |pages=191–6 |last2=Desikachar |first2=H. S. R.|issue=3}}
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.{{Cite journal | vauthors = Guttieri MJ, Peterson KM, Souza EJ |doi=10.2135/cropsci2006.03.0137 |title=Milling and Baking Quality of Low Phytic Acid Wheat | journal=Crop Science |volume=46 |pages=2403–8|issue=6|year=2006 |s2cid=33700393 }} 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.{{Citation|last1=Shitan|first1=Nobukazu|title=Chapter Nine - New Insights into the Transport Mechanisms in Plant Vacuoles|date=2013-01-01|url=http://www.sciencedirect.com/science/article/pii/B9780124076952000093|journal=International Review of Cell and Molecular Biology|volume=305|pages=383–433|editor-last=Jeon|editor-first=Kwang W.|publisher=Academic Press|language=en|access-date=2020-04-24|last2=Yazaki|first2=Kazufumi|doi=10.1016/B978-0-12-407695-2.00009-3|pmid=23890387}} Phytate variants also have the potential to be used in soil remediation, to immobilize uranium, nickel, and other inorganic contaminants.{{cite journal | vauthors = Seaman JC, Hutchison JM, Jackson BP, Vulava VM | title = In situ treatment of metals in contaminated soils with phytate | journal = Journal of Environmental Quality | volume = 32 | issue = 1 | pages = 153–61 | year = 2003 | pmid = 12549554 | doi = 10.2134/jeq2003.0153 }}
Biological effects
=Plants=
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.{{Cite book |title=Advances in Food Research |vauthors=Reddy NR, Sathe SK, Salunkhe DK |year=1982 |isbn=9780120164288 |series=Advances in Food Research |volume=28 |pages=1–92 |chapter=Phytates in legumes and cereals |doi=10.1016/s0065-2628(08)60110-x |pmid=6299067}}
=Animals=
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).{{cite journal | vauthors = Szwergold BS, Graham RA, Brown TR | title = Observation of inositol pentakis- and hexakis-phosphates in mammalian tissues by 31P NMR | journal = Biochemical and Biophysical Research Communications | volume = 149 | issue = 3 | pages = 874–81 | date = December 1987 | pmid = 3426614 | doi = 10.1016/0006-291X(87)90489-X }}{{cite journal | vauthors = Sasakawa N, Sharif M, Hanley MR | title = Metabolism and biological activities of inositol pentakisphosphate and inositol hexakisphosphate | journal = Biochemical Pharmacology | volume = 50 | issue = 2 | pages = 137–46 | date = July 1995 | pmid = 7543266 | doi = 10.1016/0006-2952(95)00059-9 }}
==In vitro==
The interaction of intracellular phytic acid with specific intracellular proteins has been investigated in vitro, and these interactions have been found to result in the inhibition or potentiation of the activities of those proteins.{{cite journal | vauthors = Hanakahi LA, Bartlet-Jones M, Chappell C, Pappin D, West SC | title = Binding of inositol phosphate to DNA-PK and stimulation of double-strand break repair | journal = Cell | volume = 102 | issue = 6 | pages = 721–9 | date = September 2000 | pmid = 11030616 | doi = 10.1016/S0092-8674(00)00061-1 | s2cid = 112839 | doi-access = free }}{{cite journal | vauthors = Norris FA, Ungewickell E, Majerus PW | title = Inositol hexakisphosphate binds to clathrin assembly protein 3 (AP-3/AP180) and inhibits clathrin cage assembly in vitro | journal = The Journal of Biological Chemistry | volume = 270 | issue = 1 | pages = 214–7 | date = January 1995 | pmid = 7814377 | doi = 10.1074/jbc.270.1.214 | doi-access = free }}
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.{{cite journal | vauthors = Dick RA, Zadrozny KK, Xu C, Schur FK, Lyddon TD, Ricana CL, Wagner JM, Perilla JR, Ganser-Pornillos BK, Johnson MC, Pornillos O, Vogt VM | title = Inositol phosphates are assembly co-factors for HIV-1 | journal = Nature | volume = 560 | issue = 7719 | pages = 509–512 | date = August 2018 | pmid = 30069050 | doi = 10.1038/s41586-018-0396-4 | pmc = 6242333 | bibcode = 2018Natur.560..509D }}
Dentistry
IP6 has potential use in endodontics, adhesive, preventive, and regenerative dentistry, and in improving the characteristics and performance of dental materials.{{Cite journal|doi = 10.3389/fmats.2021.638909|doi-access = free|title = Phytic Acid: Properties and Potential Applications in Dentistry|year = 2021|last1 = Nassar|first1 = Mohannad|last2 = Nassar|first2 = Rania|last3 = Maki|first3 = Husain|last4 = Al-Yagoob|first4 = Abdullah|last5 = Hachim|first5 = Mahmood|last6 = Senok|first6 = Abiola|last7 = Williams|first7 = David|last8 = Hiraishi|first8 = Noriko|journal = Frontiers in Materials|volume = 8|page = 29|bibcode = 2021FrMat...8...29N}}{{cite journal | vauthors = Nassar M, Nassar R, Maki H, Al-Yagoob A, Hachim M, Senok A, Williams D, Hiraishi N | title = Phytic Acid: Properties and Potential Applications in Dentistry | journal = Frontiers in Materials | date = March 2021 | volume = 8 | page = 29 | doi = 10.3389/fmats.2021.638909 | bibcode = 2021FrMat...8...29N | doi-access = free }}{{Cite journal|last1=Nassar|first1=Rania|last2=Nassar|first2=Mohannad|last3=Vianna|first3=Morgana E.|last4=Naidoo|first4=Nerissa|last5=Alqutami|first5=Fatma|last6=Kaklamanos|first6=Eleftherios G.|last7=Senok|first7=Abiola|last8=Williams|first8=David|date=2021|title=Antimicrobial Activity of Phytic Acid: An Emerging Agent in Endodontics|journal=Frontiers in Cellular and Infection Microbiology|volume=11|page=753649|doi=10.3389/fcimb.2021.753649|pmid=34765567|pmc=8576384|issn=2235-2988|doi-access=free}}
Food science
Phytic acid, mostly as phytate in the form of phytin (i.e. the calcium/magnesium salts of phytate), is found within the hulls and kernels of seeds,{{Cite journal|last1=Ellison|first1=Campbell|last2=Moreno|first2=Teresa|last3=Catchpole|first3=Owen|last4=Fenton|first4=Tina|last5=Lagutin|first5=Kirill|last6=MacKenzie|first6=Andrew|last7=Mitchell|first7=Kevin|last8=Scott|first8=Dawn|date=2021-07-01|title=Extraction of hemp seed using near-critical CO2, propane and dimethyl ether|url=https://www.sciencedirect.com/science/article/pii/S0896844621000577|journal=The Journal of Supercritical Fluids|language=en|volume=173|pages=105218|doi=10.1016/j.supflu.2021.105218|s2cid=233822572|issn=0896-8446}} including nuts, grains, and pulses.
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, and lactic acid fermentation such as in sourdough and pickling. {{cite web |url=http://agris.fao.org/agris-search/search.do?recordID=US9032841 |title=Phytates in cereals and legumes |author= |date=1989 |website=agris.fao.org |publisher=CRC Press |access-date= |quote=|archive-url=https://web.archive.org/web/20230419153827/http://agris.fao.org/agris-search/search.do?recordID=US9032841 |archive-date=2023-04-19 |url-status=dead}}
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.{{cite journal | vauthors = Phillippy BQ, Wyatt CJ | title = Degradation of phytate in foods by phytases in fruit and vegetable extracts. | journal = Journal of Food Science | date = May 2001 | volume = 66 | issue = 4 | pages = 535–539 | doi = 10.1111/j.1365-2621.2001.tb04598.x }}
As a food additive, phytic acid is used as the preservative E391.Functional Food - Improve Health through Adequate Food edited by María Chávarri Hueda, pg. 86{{Cite web|url=https://noshly.com/additive/391/preservative/391/|title=Wise Eating, Made Easy|access-date=2019-09-12|archive-date=2022-09-30|archive-url=https://web.archive.org/web/20220930123915/https://noshly.com/additive/391/preservative/391/|url-status=dead}} It is allowed as a food additive in the US (GRAS), the EU, Japan, and China. It offers some antioxidant activity by binding away iron, and is especially effective in meat. It also inhibits polyphenol oxidase, the enzyme responsible for apple browning. Basic research also suggests that it may deter the growth of pathogenic bacteria and spoilage mold.{{cite journal |last1=Bloot |first1=Ana Paula Marinho |last2=Kalschne |first2=Daneysa Lahis |last3=Amaral |first3=Joana Andrêa Soares |last4=Baraldi |first4=Ilton José |last5=Canan |first5=Cristiane |title=A Review of Phytic Acid Sources, Obtention, and Applications |journal=Food Reviews International |date=2 January 2023 |volume=39 |issue=1 |pages=73–92 |doi=10.1080/87559129.2021.1906697}}
:
:
| class="wikitable sortable"
|+ Fresh food sources of phytic acid ! rowspan=2 | Food ! colspan=2 | Proportion by weight (%) | ||
| {{abbr|Min.|Minimum}}
! {{abbr|Max.|Maximum}} | ||
|---|---|---|
| Taro | 0.143 | 0.195 |
| Cassava | 0.114 | 0.152 |
=Dietary mineral absorption=
Phytic acid has a strong affinity to the dietary trace elements, calcium, iron, and zinc, inhibiting their absorption from the small intestine.{{cite journal|pmc=4325021|year=2013|last1=Gupta|first1=R. K.|title=Reduction of phytic acid and enhancement of bioavailable micronutrients in food grains|journal=Journal of Food Science and Technology|volume=52|issue=2|pages=676–684|last2=Gangoliya|first2=S. S.|last3=Singh|first3=N. K.|pmid=25694676|doi=10.1007/s13197-013-0978-y}} Phytochemicals such as polyphenols and tannins also influence the binding.{{cite journal |vauthors=Prom-u-thai C, Huang L, Glahn RP, Welch RM, Fukai S, Rerkasem B |doi=10.1002/jsfa.2471 |title=Iron (Fe) bioavailability and the distribution of anti-Fe nutrition biochemicals in the unpolished, polished grain and bran fraction of five rice genotypes |journal=Journal of the Science of Food and Agriculture |year=2006 |volume=86 |pages=1209–15 |issue=8 |bibcode=2006JSFA...86.1209P |url=https://naldc-legacy.nal.usda.gov/naldc/download.xhtml?id=19315&content=PDF |access-date=2018-12-29 |archive-date=2020-02-23 |archive-url=https://web.archive.org/web/20200223165420/https://naldc-legacy.nal.usda.gov/naldc/download.xhtml?id=19315&content=PDF |url-status=dead }} When iron and zinc bind to phytic acid, they form insoluble precipitates and are far less absorbable in the intestines.{{cite journal | vauthors = Hurrell RF | title = Influence of vegetable protein sources on trace element and mineral bioavailability | journal = The Journal of Nutrition | volume = 133 | issue = 9 | pages = 2973S–7S | date = September 2003 | pmid = 12949395 | doi = 10.1093/jn/133.9.2973S | doi-access = free }}{{Cite book | chapter = Phytates | title = Toxicants Occurring Naturally in Foods | author = Committee on Food Protection | author2 = Food and Nutrition Board | author3 = National Research Council | publisher = National Academy of Sciences | year = 1973 | isbn = 978-0-309-02117-3 | pages = [https://archive.org/details/toxicantsoccurri0000unse/page/363 363–371] | chapter-url = https://books.google.com/books?id=lIsrAAAAYAAJ&pg=PA363 | url = https://archive.org/details/toxicantsoccurri0000unse/page/363 }}
Likewise, absorption of calcium is impaired with the result that diets high in phytates but low in calcium can result in rickets.{{Cite journal |last=Pettifor |first=John M |date=2004 |title=Nutritional rickets: deficiency of vitamin D, calcium, or both? |url=https://linkinghub.elsevier.com/retrieve/pii/S0002916522037741 |journal=The American Journal of Clinical Nutrition |language=en |volume=80 |issue=6 |pages=1725S–1729S |doi=10.1093/ajcn/80.6.1725S}}
Because phytic acid also can affect the absorption of iron, "dephytinization should be considered as a major strategy to improve iron nutrition during the weaning period".{{cite journal | vauthors = Hurrell RF, Reddy MB, Juillerat MA, Cook JD | title = Degradation of phytic acid in cereal porridges improves iron absorption by human subjects | journal = The American Journal of Clinical Nutrition | volume = 77 | issue = 5 | pages = 1213–9 | date = May 2003 | pmid = 12716674 | doi = 10.1093/ajcn/77.5.1213 | citeseerx = 10.1.1.333.4941 }} Dephytinization by exogenous phytase to 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 breeding to increase mineral density (biofortification) or reducing phytate content are under preliminary research.{{cite journal | last=Raboy | first=Victor | title=Low phytic acid crops: Observations based on four decades of research | journal=Plants | volume=9 | issue=2 | date=22 January 2020 | issn=2223-7747 | pmid=31979164 | doi=10.3390/plants9020140 | page=140| pmc=7076677 | doi-access=free }}
Fire retarding agent
Recently, phytic acid, in combination with other chemicals like silicates or other, has been increasingly used to enhance the fire retardancy of various composite materials.{{cite journal | last=Lin | first=Chia-Feng | last2=Zhang | first2=Chi | last3=Karlsson | first3=Olov | last4=Martinka | first4=Jozef | last5=Mantanis | first5=George I. | last6=Rantuch | first6=Peter | last7=Jones | first7=Dennis | last8=Sandberg | first8=Dick | author5-link=George Mantanis |title=Phytic Acid-Silica System for Imparting Fire Retardancy in Wood Composites | journal=Forests | publisher=MDPI AG | volume=14 | issue=5 | date=2023-05-16 | issn=1999-4907 | doi=10.3390/f14051021 | doi-access=free | page=1021}}{{cite journal | last=Zhang | first=Mengfei | last2=Wang | first2=Yang | last3=Huang | first3=Jing | last4=Wang | first4=Dong | last5=Li | first5=Ting | last6=Wang | first6=Shibo | last7=Dong | first7=Weifu | title=Phytic acid–based flame retardant and its application to poly(lactic acid) composites | journal=New Journal of Chemistry | publisher=Royal Society of Chemistry (RSC) | volume=47 | issue=42 | year=2023 | issn=1144-0546 | doi=10.1039/d3nj03460g | pages=19494–19503}}
See also
{{Commons category}}
References
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{{Purinergics}}
{{Authority control}}
{{DEFAULTSORT:Phytic Acid}}