| Revision as of 13:44, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475431263 of page Pantothenic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 03:33, 10 November 2024 edit David notMD (talk | contribs)Extended confirmed users, Rollbackers59,269 edits Undid revision 1256364332 by 2A01:CB00:881:C000:1CD6:D4F:4AAE:68B8 (talk) restoring text and a referenceTag: Undo |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{distinguish|pantethine}} |
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{{chembox |
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{{good article}} |
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{{Use dmy dates|date=March 2020}} |
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{{Chembox |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 464185145 |
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| verifiedrevid = 477003091 |
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|ImageFile=Pantothenic acid structure.svg |
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| ImageFile = (R)-Pantothenic acid Formula V.1.svg |
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|ImageSize=200px |
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| ImageSize = |
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| ImageName = Skeletal formula of (R)-pantothenic acid |
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|ImageFile2=Pantothenic_acid_3D.png |
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| ImageClass = skin-invert-image |
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|ImageSize=200px |
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| ImageFile1 = Pantothenic-acid-based-on-xtal-3D-bs-17.png |
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|IUPACName=3-propanoic acid |
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| ImageSize1 = |
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|OtherNames= |
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| ImageName1 = Pantothenic acid molecule |
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|Section1= {{Chembox Identifiers |
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| PIN = 3-propanoic acid |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SystematicName = 3-propanoic acid |
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| ChemSpiderID = 6361 |
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|Section1={{Chembox Identifiers |
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| CASNo = 599-54-2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 79-83-4 |
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| CASNo1_Comment = (''R'') |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| PubChem = 988 |
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| PubChem1 = 6613 |
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| PubChem1_Comment = (''R'') |
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| PubChem2 = 5748353 |
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| PubChem2_Comment = (''S'') |
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| ChemSpiderID = 963 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1 = 6361 |
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| ChemSpiderID1_Comment = (''R'') |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID2 = 4677898 |
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| ChemSpiderID2_Comment = (''S'') |
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| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 568ET80C3D |
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| UNII = 66Y94D1203 |
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| UNII1 = 19F5HK2737 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1_Comment = (''R'') |
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| EC_number = 209-965-4 |
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| DrugBank = DB01783 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| KEGG = D07413 |
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| KEGG = D07413 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChI = 1/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)/t7-/m0/s1 |
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| MeSHName = Pantothenic+Acid |
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| InChIKey = GHOKWGTUZJEAQD-ZETCQYMHBS |
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| ChEBI = 7916 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1594 |
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| ChEMBL = 1594 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| Beilstein = 1727062, 1727064 (''R'') |
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| StdInChI = 1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)/t7-/m0/s1 |
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| 3DMet = B00193 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| SMILES = CC(C)(CO)C(C(=O)NCCC(=O)O)O |
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| StdInChIKey = GHOKWGTUZJEAQD-ZETCQYMHSA-N |
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| SMILES1 = CC(C)(CO)(C(=O)NCCC(=O)O)O |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| SMILES1_Comment = (''R'') |
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| CASNo=79-83-4 |
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| SMILES2 = CC(C)(CO)(C(=O)NCCC(=O)O)O |
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| PubChem = 6613 |
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| SMILES2_Comment = (''S'') |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| StdInChI = 1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13) |
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| ChEBI = 46905 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = GHOKWGTUZJEAQD-UHFFFAOYSA-N |
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| DrugBank = DB01783 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| SMILES = O=C(NCCC(=O)O)(O)C(C)(C)CO |
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| RTECS = RU4729000 |
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| ATCCode_prefix = A11 |
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}} |
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| ATCCode_suffix = HA31 |
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|Section2={{Chembox Properties |
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| ATC_Supplemental = {{ATC|D03|AX04}} (calcium salt) |
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| C=9 | H=17 | N=1 | O=5 |
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}} |
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| Density = 1.266 g/cm<sup>3</sup><br/> 1.32 g/cm<sup>3</sup> (Ca<sup>2+</sup> salt)<ref name=eu>{{cite journal|title = Scientific Opinion on the safety and efficacy of pantothenic acid (calcium D-pantothenate and D-panthenol) as a feed additive for all animal species based on a dossier submitted by Lohmann Animal Health|journal = EFSA Journal|volume = 9|issue = 11|pages = 2409|publisher = ]|place = ]|year = 2011|doi = 10.2903/j.efsa.2011.2409|doi-access = }}</ref> |
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|Section2= {{Chembox Properties |
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| Appearance = Yellow oil<br/> Colorless crystals (Ca<sup>2+</sup> salt) |
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| C=9|H=17|N=1|O=5 |
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| Odor = Odorless |
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| Appearance= |
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| MeltingPtC = 183.833 |
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| Density=1.266 g/cm³ |
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| MeltingPt_notes = <br/> {{convert|196-200|C|F K}}<br/> decomposes (Ca<sup>2+</sup> salt)<ref name=eu /><ref name=chemicalland>{{cite web|url = http://www.chemicalland21.com/lifescience/foco/CALCIUM%20PANTOTHENATE.htm|title = Calcium D-pantothenate|access-date = 2014-09-05|publisher = CHEMICALLAND21, AroKor Holdings Inc.}}</ref><ref name=mod /> |
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| MeltingPtC=183.83 |
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| LogP = −1.416<ref name=hmdbsa>{{cite web|url = http://www.hmdb.ca/system/metabolites/msds/000/000/148/original/HMDB00210.pdf?1358462271|title = MSDS of D-pantothenic acid|publisher = Human Metabolome Database|access-date = 2014-09-05}}</ref> |
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| BoilingPtC=551.5 |
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| pKa = 4.41<ref name=mod>{{cite book|title = Modern Chromatographic Analysis of Vitamins: Revised And Expanded|edition = 3rd|volume = 84|series = Chromatographic Science|editor-first1 = André P. De|editor-last1 = Leenheer|editor-first2 = Willy E.|editor-last2 = Lambert|editor-first3 = Jan F. Van|editor-last3 = Bocxlaer |url = https://books.google.com/books?id=8UppGvIN_t0C&pg=PA533|publisher = ]|year = 2000|isbn = 978-0-203-90962-1|page = 533}}</ref> |
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| Solubility= |
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| pKb = 9.698 |
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| Solubility = Very soluble<ref name=crc>{{CRC90}}</ref><br/> 2.11 g/mL (Ca<sup>2+</sup> salt)<ref name=eu /> |
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| SolubleOther = Very soluble in ], ]<ref name=crc /><br/>Ca<sup>2+</sup> salt:<br/>Slightly soluble in ], ]<ref name=chemicalland /> |
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| SpecRotation = +37.5°<br/> +24.3° (Ca<sup>2+</sup> salt)<ref name=mod /> |
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}} |
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|Section7={{Chembox Hazards |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| LD50 = > 10 mg/g (Ca<sup>2+</sup> salt)<ref name=chemicalland /> |
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}} |
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}} |
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|Section3= {{Chembox Hazards |
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|Section9={{Chembox Related |
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| OtherFunction_label = alkanoic acids |
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| MainHazards= |
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| OtherFunction = ]<br/>]<br/>] |
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| FlashPt= |
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| OtherCompounds = ] |
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'''Pantothenic acid''' ('''vitamin B<sub>5</sub>''') is a ] and an ].<ref name="ods">{{cite web|title=Pantothenic acid: Fact Sheet for Health Professionals|publisher=Office of Dietary Supplements, US National Institutes of Health|date=3 June 2020|url=https://ods.od.nih.gov/factsheets/PantothenicAcid-HealthProfessional/|access-date=27 November 2020}}</ref> All animals need pantothenic acid in order to synthesize ] (CoA), which is essential for cellular energy production and for the synthesis and degradation of ]s, ]s, and ]s.<ref name="ods" /><ref name=lpi/> |
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Pantothenic acid is the combination of ] and ]. Its name comes from the ] {{lang|grc|πάντοθεν}} ''pantothen'', meaning "from everywhere", because pantothenic acid, at least in small amounts, is in almost all foods.<ref name="ods" /><ref name=usda/><ref name="lpi">{{cite web |publisher=Linus Pauling Institute at Oregon State University. Micronutrient Information Center |title=Pantothenic acid |date=1 July 2015|access-date=27 November 2020 |url=http://lpi.oregonstate.edu/infocenter/vitamins/pa/ }}</ref> Deficiency of pantothenic acid is very rare in humans.<ref name="ods" /><ref name=lpi/> In dietary supplements and animal feed, the form commonly used is calcium pantothenate, because chemically it is more stable, and hence makes for longer product shelf-life, than sodium pantothenate and free pantothenic acid.<ref name=eu /> |
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==Definition== |
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] |
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Pantothenic acid is a water-soluble ], one of the ]s. It is synthesized from the amino acid β-alanine and pantoic acid (see ] and structure of coenzyme A figures). Unlike ] or ], which occurs in several chemically related forms known as ]s, pantothenic acid is only one chemical compound. It is a starting compound in the synthesis of ] (CoA), a cofactor for many enzyme processes.<ref name=lpi/><ref name=PKIN2012Panto /><ref name="DRItext" /> |
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==Use in biosynthesis of coenzyme A== |
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] |
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Pantothenic acid is a precursor to CoA via a five-step process. The biosynthesis requires pantothenic acid, cysteine, and four equivalents of ATP (see figure).<ref name=Leonardi2005>{{cite journal |title=Coenzyme A: back in action |last1=Leonardi |first1=R |last2=Zhang |first2=Y-M |last3=Rock |first3=CO |last4=Jackowski |first4=S |year=2005 |doi=10.1016/j.plipres.2005.04.001 |journal=Progress in Lipid Research |volume=44 |pages=125–53 |pmid=15893380 |issue=2–3}}</ref> |
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# Pantothenic acid is ] to 4′-phosphopantothenate by the enzyme ]. This is the committed step in CoA biosynthesis and requires ATP.<ref name=Leonardi2007>{{cite journal|last1=Leonardi|first1=R|last2=Jackowski|first2=S|date=April 2007|title=Biosynthesis of Pantothenic Acid and Coenzyme A|journal=EcoSal Plus|volume=2|issue=2|doi=10.1128/ecosalplus.3.6.3.4|issn=2324-6200|pmc=4950986|pmid=26443589}}</ref> |
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# A ] is added to 4′-phosphopantothenate by the enzyme ] to form 4'-phospho-N-pantothenoylcysteine (PPC). This step is coupled with ].<ref name=Leonardi2007 /> |
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# PPC is ] to ] by ] |
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# 4′-Phosphopantetheine is adenylated (or more properly, ]) to form dephospho-CoA by the enzyme ] |
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# Finally, dephospho-CoA is phosphorylated to coenzyme A by the enzyme ]. This final step also requires ATP.<ref name=Leonardi2007 /> |
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This pathway is suppressed by ], meaning that CoA is a competitive inhibitor of pantothenate kinase, the enzyme responsible for the first step.<ref name=Leonardi2007 /> |
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Coenzyme A is necessary in the reaction mechanism of the ]. This process is the body's primary ] and is essential in breaking down the building blocks of the cell such as ]s, ]s and ]s, for fuel.<ref>{{cite book |last1=Alberts|first1=B|last2=Johnson|first2=A|last3=Lewis|first3=J |last4=Raff|first4=M|last5=Roberts|first5=K|last6=Walter|first6=P|date=2002|title=Molecular Biology of the Cell |edition=4th |chapter=Chapter 2: How Cells Obtain Energy from Food |publisher=Garland Science|url=https://www.ncbi.nlm.nih.gov/books/NBK26882/ |language=en}}</ref> CoA is important in energy metabolism for ] to enter the ] (TCA cycle) as acetyl-CoA, and for ] to be transformed to ] in the cycle.<ref name="Gropper_2009">{{cite book | vauthors = Gropper SS, Smith JL, Groff JL | date = 2018 | title = Advanced Nutrition and Human Metabolism (7th Ed.)|pages=330–335 | location = Belmont, CA | publisher = Wadsworth, Cengage Learning | isbn = 978-1-305-62785-7}}</ref> CoA is also required for acylation and acetylation, which, for example, are involved in ], and various enzyme functions.<ref name="Gropper_2009" /> In addition to functioning as CoA, this compound can act as an ] group carrier to form ] and other related compounds; this is a way to transport ] atoms within the cell.<ref name=PKIN2012Panto /> CoA is also required in the formation of ] (ACP),<ref>{{cite book | vauthors = Sweetman L | date = 2005 | chapter = Pantothenic Acid. | veditors = Coates PM, Blackman MR, Cragg GM, Levine MA, White JD, Moss J | title = Encyclopedia of Dietary Supplements | volume = 1 | pages = 517–525 | publisher = CRC Press | isbn = 978-0-8247-5504-1 | edition = First }}</ref> which is required for fatty acid synthesis.<ref name=PKIN2012Panto /><ref>{{cite journal|last1=Shi|first1=L|last2=Tu|first2=BP|date=April 2015|title=Acetyl-CoA and the Regulation of Metabolism: Mechanisms and Consequences|journal=Current Opinion in Cell Biology|volume=33|pages=125–31|doi=10.1016/j.ceb.2015.02.003|issn=0955-0674|pmc=4380630|pmid=25703630}}</ref> Its synthesis also connects with other vitamins such as thiamin and folic acid.<ref>{{cite journal |last1=Roberta |first1=Leonardi |title=Biosynthesis of Pantothenic Acid and Coenzyme A |journal=EcoSal Plus |date=2007 |volume=2 |issue=2 |pages=10.1128/ecosalplus.3.6.3.4 |doi=10.1128/ecosalplus.3.6.3.4 |pmid=26443589 |pmc=4950986 }}</ref> |
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==Dietary recommendations== |
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The US Institute of Medicine (IOM) updated Estimated Average Requirements (EARs) and Recommended Dietary Allowances (RDAs) for B vitamins in 1998. At that time, there was not sufficient information to establish EARs and RDAs for pantothenic acid. In instances such as this, the Board sets Adequate Intakes (AIs), with the understanding that at some later date, AIs may be replaced by more exact information.<ref name="DRItext" /><ref name=DRIExplain>{{cite web |url=https://ods.od.nih.gov/Health_Information/Dietary_Reference_Intakes.aspx |
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|title=Nutrient Recommendations: Dietary Reference Intakes (DRI) |website=National Institutes of Health, Office of Dietary Supplements |access-date=30 June 2020}}</ref> |
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The current AI for teens and adults ages 14 and up is 5 mg/day. This was based in part on the observation that for a typical diet, urinary excretion was approximately 2.6 mg/day, and that ] of food-bound pantothenic acid was roughly 50%.<ref name="DRItext" /> AI for pregnancy is 6 mg/day. AI for ] is 7 mg/day. For infants up to 12 months, the AI is 1.8 mg/day. For children ages 1–13 years, the AI increases with age from 2 to 4 mg/day. Collectively the EARs, RDAs, AIs and ULs are referred to as ]s (DRIs).<ref name="DRItext">{{cite book | last1 = Institute of Medicine | title = Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline | chapter = Pantothenic Acid | publisher = The National Academies Press | year = 1998 | location = Washington, DC | pages = 357–373 | chapter-url = http://www.nap.edu/openbook.php?record_id=6015&page=357 | access-date = 2017-08-29 | isbn = 978-0-309-06554-2| author1-link = Institute of Medicine }}</ref><ref name=DRIExplain /> |
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{| class="wikitable" |
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! Age group |
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! Age |
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! Adequate intake<ref name="DRItext" /> |
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| Infants |
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| 0–6 months |
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| 1.7 mg |
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| Infants |
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| 7–12 months |
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| 1.8 mg |
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| Children |
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| 1–3 years |
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| 2 mg |
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| Children |
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| 4–8 years |
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| 3 mg |
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| Children |
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| 9–13 years |
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| 4 mg |
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| Adult men and women |
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| 14+ years |
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| 5 mg |
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| Pregnant women |
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| (vs. 5) |
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| 6 mg |
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| Breastfeeding women |
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| (vs. 5) |
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| 7 mg |
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While for many nutrients, the US Department of Agriculture uses food composition data combined with food consumption survey results to estimate average consumption, the surveys and reports do not include pantothenic acid in the analyses.<ref>{{cite web |url=https://www.ars.usda.gov/ARSUserFiles/80400530/pdf/1314/Table_1_NIN_GEN_13.pdf |title=TABLE 1: Nutrient Intakes from Food and Beverages|website=What We Eat In America, NHANES 2012–2014 (2016)|access-date=18 August 2018}}</ref> Less formal estimates of adult daily intakes report about 4 to 7 mg/day.<ref name="DRItext" /> |
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The ] (EFSA) refers to the collective set of information as Dietary Reference Values, with Population Reference Intake (PRI) instead of RDA, and Average Requirement instead of EAR. AI and UL are defined the same as in the US. For women and men over age 11, the Adequate Intake (AI) is set at 5 mg/day. AI for pregnancy is 5 mg/day, for lactation 7 mg/day. For children ages 1–10 years, the AI is 4 mg/day. These AIs are similar to the US AIs.<ref>{{cite web | title = Overview on Dietary Reference Values for the EU population as derived by the EFSA Panel on Dietetic Products, Nutrition and Allergies| year = 2017| url = https://www.efsa.europa.eu/sites/default/files/assets/DRV_Summary_tables_jan_17.pdf}}</ref> |
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===Safety=== |
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As for safety, the IOM sets ]s (ULs) for vitamins and minerals when evidence is sufficient. In the case of pantothenic acid, there is no UL, as there is no human data for adverse effects from high doses.<ref name="DRItext" /> The EFSA also reviewed the safety question and reached the same conclusion as in the United States – that there was not sufficient evidence to set a UL for pantothenic acid.<ref>{{cite web | title = Tolerable Upper Intake Levels For Vitamins And Minerals| publisher = European Food Safety Authority| year = 2006| url = http://www.efsa.europa.eu/sites/default/files/efsa_rep/blobserver_assets/ndatolerableuil.pdf}}</ref> |
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===Labeling requirements=== |
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For US food and dietary supplement labeling purposes, the amount in a serving is expressed as a percent of Daily Value (%DV). For pantothenic acid labeling purposes, 100% of the Daily Value was 10 mg, but as of May 2016 it was revised to 5 mg to bring it into agreement with the AI.<ref name="FedReg">{{cite web|url=https://www.gpo.gov/fdsys/pkg/FR-2016-05-27/pdf/2016-11867.pdf |title=Federal Register May 27, 2016 Food Labeling: Revision of the Nutrition and Supplement Facts Labels}}</ref><ref>{{cite web | title=Daily Value Reference of the Dietary Supplement Label Database (DSLD) | website=Dietary Supplement Label Database (DSLD) | url=https://www.dsld.nlm.nih.gov/dsld/dailyvalue.jsp | access-date=16 May 2020 | archive-date=7 April 2020 | archive-url=https://web.archive.org/web/20200407073956/https://dsld.nlm.nih.gov/dsld/dailyvalue.jsp | url-status=dead }}</ref> |
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Compliance with the updated labeling regulations was required by January 2020 for manufacturers with ]10 million or more in annual food sales, and by January 2021 for manufacturers with lower volume food sales.<ref name="FDAdelay">{{cite web | title=Changes to the Nutrition Facts Label | website=U.S. ] (FDA) | date=27 May 2016 | url=https://www.fda.gov/food/food-labeling-nutrition/changes-nutrition-facts-label | access-date=16 May 2020}} {{PD-notice}}</ref><ref>{{cite web | title=Industry Resources on the Changes to the Nutrition Facts Label | website=U.S. ] (FDA) | date=21 December 2018 | url=https://www.fda.gov/food/food-labeling-nutrition/industry-resources-changes-nutrition-facts-label | access-date=16 May 2020}} {{PD-notice}}</ref> A table of the old and new adult daily values is provided at ]. |
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==Sources== |
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===Dietary=== |
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Food sources of pantothenic acid include animal-sourced foods, including dairy foods and eggs.<ref name=ods/><ref name="usda">{{cite web|publisher=US Department of Agriculture Agricultural Research Service, Food Data Central |url=https://www.ars.usda.gov/northeast-area/beltsville-md-bhnrc/beltsville-human-nutrition-research-center/methods-and-application-of-food-composition-laboratory/mafcl-site-pages/sr-legacy-nutrient-search/ |title=Pantothenic acid ordered by nutrient content per 100 g |access-date=3 June 2020 |date= February 2020}}</ref> Potatoes, tomato products, oat-cereals, sunflower seeds, avocado are good plant sources. Mushrooms are good sources, too. Whole grains are another source of the vitamin, but milling to make white rice or white flour removes much of the pantothenic acid, as it is found in the outer layers of whole grains.<ref name="ods" /><ref name="DRItext" /> In animal feeds, the most important sources are alfalfa, cereal, fish meal, peanut meal, molasses, rice bran, wheat bran, and yeasts.<ref name=Combs2007 /> |
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===Supplements=== |
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] of pantothenic acid commonly use ] (or ''panthenol''), a ] ], which is converted to pantothenic acid once consumed.<ref name=lpi/> Calcium pantothenate – a ] – may be used in manufacturing because it is more resistant than pantothenic acid to factors that deteriorate stability, such as acid, ] or heat.<ref name=PKIN2012Panto /><ref name=Combs2007 /> The amount of pantothenic acid in dietary supplement products may contain up to 1,000 mg (200 times the Adequate Intake level for adults), without evidence that such large amounts provide any benefit.<ref name=lpi/><ref name=ods/> According to ], pantothenic acid supplements have a long list of claimed uses, but there is insufficient scientific evidence to support any of them.<ref>{{cite web |url=https://www.webmd.com/vitamins/ai/ingredientmono-853/pantothenic-acid-vitamin-b5 |title=Pantothenic acid (Vitamin B5) |date= 2018 |website=WebMD |access-date=22 June 2020}}</ref> |
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As a dietary supplement, pantothenic acid is not the same as ], which is composed of two pantothenic acid molecules linked by a ] bridge.<ref name=lpi/> Sold as a high-dose supplement (600 mg), pantethine may be effective for lowering blood levels of ] – a ] for cardiovascular diseases – but its long-term effects are unknown, so use should be supervised by a physician.<ref name=lpi/> Dietary supplementation with pantothenic acid does not have the cholesterol-lowering effect as pantethine.<ref name=PKIN2012Panto /> |
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===Fortification=== |
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According to the Global Fortification Data Exchange, pantothenic acid deficiency is so rare that no countries require that foods be fortified.<ref name=Map>{{cite web|url=https://fortificationdata.org/map-number-of-nutrients/|title=Map: Count of Nutrients In Fortification Standards|website=Global Fortification Data Exchange|access-date=30 April 2019}}</ref> |
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==Absorption, metabolism and excretion== |
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When found in foods, most pantothenic acid is in the form of CoA or bound to ] (ACP). For the intestinal cells to absorb this vitamin, it must be converted into free pantothenic acid. Within the ] of the intestine, CoA and ACP are ] into 4'-phosphopantetheine. The 4'-phosphopantetheine is then ] into ]. ], an intestinal enzyme, then hydrolyzes pantetheine into free pantothenic acid.<ref name="Trumbo">{{cite book | vauthors = Trumbo PR |year=2006 |chapter=Pantothenic Acid | veditors = Shils ME, Shike M, Ross AC, Caballero B, Cousins RJ |title=Modern Nutrition in Health and Disease |edition=10th |pages=462–467 |location=Philadelphia, PA |publisher=Lippincott Williams & Wilkins |isbn=978-0-7817-4133-0 }}</ref> Free pantothenic acid is absorbed into intestinal cells via a saturable, sodium-dependent active transport system.<ref name="Gropper_2009"/> At high levels of intake, when this mechanism is saturated, some pantothenic acid may also be additionally absorbed via passive diffusion.<ref name=Combs2007 /> As a whole, when intake increases 10-fold, absorption rate decreases to 10%.<ref name="Gropper_2009"/> |
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Pantothenic acid is excreted in urine. This occurs after its release from CoA. Urinary amounts are on the order of 2.6 mg/day, but decreased to negligible amounts when subjects in multi-week experimental situations were fed diets devoid of the vitamin.<ref name="DRItext" /> |
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==Deficiency== |
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Pantothenic acid deficiency in humans is very rare and has not been thoroughly studied. In the few cases where deficiency has been seen (prisoners of war during World War II, victims of starvation, or limited volunteer trials), nearly all symptoms were reversed with orally administered pantothenic acid.<ref name="Gropper_2009"/><ref name=PKIN2012Panto /> Symptoms of deficiency are similar to other ] deficiencies. There is impaired energy production, due to low CoA levels, which could cause symptoms of irritability, ], and ].<ref name="Gropper_2009"/> Acetylcholine synthesis is also impaired; therefore, neurological symptoms can also appear in deficiency;<ref name=DRIGuide2006>{{cite book | url=https://www.nap.edu/read/11537/chapter/29 |veditors=Otten JJ, Hellwig JP, Meyers LD | date = 2006 | title = Dietary Reference Intakes: The Essential Guide to Nutrient Requirements |chapter=Pantothenic Acid | location = Washington, DC |pages=270–273|isbn=0-309-10091-7| publisher = The National Academies Press |doi=10.17226/11537 }}</ref> they include sensation of numbness in hands and feet, ] and muscle cramps. Additional symptoms could include restlessness, malaise, sleep disturbances, nausea, vomiting and abdominal cramps.<ref name=DRIGuide2006 /> |
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In animals, symptoms include disorders of the nervous, gastrointestinal, and immune systems, reduced growth rate, decreased food intake, skin lesions and changes in hair coat, and alterations in lipid and carbohydrate metabolism.<ref>{{cite journal | vauthors = Smith CM, Song WO |year=1996 |title=Comparative nutrition of pantothenic acid |journal=Journal of Nutritional Biochemistry |volume=7 |issue=6 |pages=312–321 |doi=10.1016/0955-2863(96)00034-4 }}</ref> In rodents, there can be loss of hair color, which led to marketing of pantothenic acid as a dietary supplement which could prevent or treat graying of hair in humans (despite the lack of any human trial evidence).<ref name=PKIN2012Panto /> |
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Pantothenic acid status can be assessed by measuring either whole blood concentration or 24-hour urinary excretion. In humans, whole blood values less than 1 μmol/L are considered low, as is urinary excretion of less than 4.56 mmol/day.<ref name=PKIN2012Panto /> |
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==Animal nutrition== |
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Calcium pantothenate and dexpanthenol (D-panthenol) are European Food Safety Authority (EFSA) approved additives to animal feed.<ref name=eu /> Supplementation is on the order of 8–20 mg/kg for pigs, 10–15 mg/kg for poultry, 30–50 mg/kg for fish and 8–14 mg/kg feed for pets. These are recommended concentrations, designed to be higher than what are thought to be requirements.<ref name=eu /> There is some evidence that feed supplementation increases pantothenic acid concentration in tissues, i.e., meat, consumed by humans, and also for eggs, but this raises no concerns for consumer safety.<ref name=eu /> |
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No dietary requirement for pantothenic acid has been established in ruminant species. Synthesis of pantothenic acid by ] microorganisms appears to be 20 to 30 times more than dietary amounts.<ref>{{cite journal |vauthors=Ragaller V, Lebzien P, Südekum KH, Hüther L, Flachowsky G |title=Pantothenic acid in ruminant nutrition: a review |journal=Journal of Animal Physiology and Animal Nutrition |volume=95 |issue=1 |pages=6–16 |date=February 2011 |pmid=20579186 |doi=10.1111/j.1439-0396.2010.01004.x |doi-access=free }}</ref> Net microbial synthesis of pantothenic acid in the rumen of steer calves has been estimated to be 2.2 mg/kg of digestible organic matter consumed per day. Supplementation of pantothenic acid at 5 to 10 times theoretical requirements did not improve growth performance of feedlot cattle.<ref>{{cite book | author = National Research Council | date = 2001 |pages=162–177| title = Nutrient Requirements of Dairy Cattle | edition = 7th | publisher = National Academy of Sciences | location = Washington, DC }}</ref> |
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==Synthesis== |
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===Biosynthesis=== |
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] |
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Bacteria synthesize pantothenic acid from the amino acids aspartate and a precursor to the amino acid valine. Aspartate is converted to ]. The amino group of valine is replaced by a keto-] to yield ], which, in turn, forms α-ketopantoate following transfer of a methyl group, then D-pantoate (also known as pantoic acid) following reduction. β-alanine and pantoic acid are then condensed to form pantothenic acid (see figure).<ref name=Leonardi2007 /> |
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===Industrial synthesis=== |
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The industrial synthesis of pantothenic acid starts with the ] of ] and ]. The resulting ] is converted to its ] derivative. which is cyclised to give ] pantolactone. This sequence of reactions was first published in 1904.<ref>{{cite journal|last=Glaser|first=Erhard |title=Über die Einwirkung von Blausäure auf Methyloldimethylacetaldehyd |journal=Monatshefte für Chemie |volume=25 |issue=1 |year=1904 |pages=46–54 |doi=10.1007/bf01540191 |s2cid=97862109 |url=https://zenodo.org/record/2353575 |language=de}}</ref> |
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:] |
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Synthesis of the vitamin is completed by ] of the lactone using ], for example, followed by treatment with the calcium or sodium salt of β-alanine.<ref>{{cite journal |doi=10.1002/anie.201205886 |title=One Hundred Years of Vitamins-A Success Story of the Natural Sciences |year=2012 |last1=Eggersdorfer |first1=Manfred |last2=Laudert |first2=Dietmar |last3=Létinois |first3=Ulla |last4=McClymont |first4=Tom |last5=Medlock |first5=Jonathan |last6=Netscher |first6=Thomas |last7=Bonrath |first7=Werner |journal=Angewandte Chemie International Edition |volume=51 |issue=52 |page=12975 |pmid=23208776 }}</ref> |
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==History== |
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{{Further|Vitamin#History}} |
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The term ''vitamin'' is derived from the word ''vitamine'', which was coined in 1912 by Polish biochemist ], who isolated a complex of water-soluble micronutrients essential to life, all of which he presumed to be ]s.<ref name = "Funk">{{cite journal |last1=Funk |first1=C |title=The etiology of the deficiency diseases. Beri-beri, polyneuritis in birds, epidemic dropsy, scurvy, experimental scurvy in animals, infantile scurvy, ship beri-beri, pellagra |journal=Journal of State Medicine |date=1912 |volume=20 |pages=341–68 |url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015069802166&view=1up&seq=351}}</ref> When this presumption was later determined not to be true, the "e" was dropped from the name, hence "vitamin".<ref name=Combs2007>{{cite book|url=https://books.google.com/books?id=1CMHiWum0Y4C&pg=PA16|title=The Vitamins: Fundamental Aspects in Nutrition and Health (3rd ed.). | first=Gerald F. | last = Combs |date=2007|pages=7–33|publisher=Elsevier, Boston, MA|isbn=978-0-080-56130-1}}</ref> Vitamin nomenclature was alphabetical, with ] calling these fat-soluble A and water-soluble B.<ref name=Combs2007 /> Over time, eight chemically distinct, water-soluble B vitamins were isolated and numbered, with pantothenic acid as vitamin B<sub>5</sub>.<ref name=Combs2007 /> |
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The essential nature of pantothenic acid was discovered by ] in 1933 by showing it was required for the growth of yeast.<ref>{{cite journal |last=Richards |first=OW |year=1936 |title=The Stimulation of Yeast Proliferation By Pantothenic Acid |journal=Journal of Biological Chemistry |volume=113 |issue=2 |pages=531–36 |doi=10.1016/S0021-9258(18)74874-6 |url=http://www.jbc.org/content/113/2/531.full.pdf |doi-access=free }}</ref> Three years later Elvehjem and Jukes demonstrated that it was a growth and anti-dermatitis factor in chickens.<ref name=PKIN2012Panto>{{cite book |last1=Miller|first1= JW| last2=Rucker|first2=RB |title = Present Knowledge in Nutrition, Eleventh Edition |chapter = Pantothenic Acid |editor=BP Marriott |editor2=DF Birt |editor3=VA Stallings|editor4=AA Yates |publisher = Academic Press (Elsevier) |year=2020 |location = London, United Kingdom |pages = 273–88 |isbn=978-0-323-66162-1}}</ref> Williams dubbed the compound "pantothenic acid", deriving the name from the Greek word ''pantothen'', which translates as "from everywhere". His reason was that he found it to be present in almost every food he tested.<ref name=PKIN2012Panto /> Williams went on to determine the chemical structure in 1940.<ref name=PKIN2012Panto /> In 1953, ] shared the ] "for his discovery of co-enzyme A and its importance for intermediary metabolism", work he had published in 1946.<ref>{{cite journal|last1=Kresge|first1=N|last2=Simoni|first2=RD|last3=Hill|first3=RL|date=May 2005|title=Fritz Lipmann and the Discovery of Coenzyme A|url=http://www.jbc.org/content/280/21/e18|journal=Journal of Biological Chemistry|volume=280|issue=21|pages=e18|issn=0021-9258|access-date=28 June 2020|archive-date=12 April 2019|archive-url=https://web.archive.org/web/20190412153806/http://www.jbc.org/content/280/21/e18|url-status=dead}}</ref> |
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== References == |
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{{reflist|30em}} |
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{{Vitamins}} |
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{{Dietary supplement}} |
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{{Metabolism of vitamins, coenzymes, and cofactors}} |
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{{Preparations for treatment of wounds and ulcers}} |
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{{Cholinergics}} |
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{{Authority control}} |
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{{DEFAULTSORT:Pantothenic Acid}} |
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] |
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] |
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] |