Pantothenic acid

Pantothenic acid
Skeletal formula of (R)-pantothenic acid
Pantothenic acid molecule
Names
Preferred IUPAC name
3-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanamido]propanoic acid
Systematic IUPAC name
3-[(2R)-(2,4-Dihydroxy-3,3-dimethylbutanoyl)amino]propanoic acid
Identifiers
3D model (JSmol)
3DMet
1727062, 1727064 (R)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.009.061 Edit this at Wikidata
EC Number
  • 209-965-4
KEGG
MeSH Pantothenic+Acid
RTECS number
  • RU4729000
UNII
  • InChI=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) ☒N
    Key: GHOKWGTUZJEAQD-UHFFFAOYSA-N ☒N
  • CC(C)(CO)C(C(=O)NCCC(=O)O)O
  • (R): CC(C)(CO)[C@H](C(=O)NCCC(=O)O)O
  • (S): CC(C)(CO)[C@@H](C(=O)NCCC(=O)O)O
Properties
C9H17NO5
Molar mass 219.237 g·mol−1
Appearance Yellow oil
Colorless crystals (Ca2+ salt)
Odor Odorless
Density 1.266 g/cm3
1.32 g/cm3 (Ca2+ salt)[1]
Melting point 183.833 °C (362.899 °F; 456.983 K)
196–200 °C (385–392 °F; 469–473 K)
decomposes (Ca2+ salt)[1][3][5]
Very soluble[2]
2.11 g/mL (Ca2+ salt)[1]
Solubility Very soluble in C6H6, ether[2]
Ca2+ salt:
Slightly soluble in alcohol, CHCl3[3]
log P −1.416[4]
Acidity (pKa) 4.41[5]
Basicity (pKb) 9.698
+37.5°
+24.3° (Ca2+ salt)[5]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Lethal dose or concentration (LD, LC):
> 10 mg/g (Ca2+ salt)[3]
Related compounds
Related alkanoic acids
Arginine
Hopantenic acid
4-(γ-Glutamylamino)butanoic acid
Related compounds
Panthenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pantothenic acid (vitamin B5) is a B vitamin and an essential nutrient.[6] All animals need pantothenic acid in order to synthesize coenzyme A (CoA), which is essential for cellular energy production and for the synthesis and degradation of proteins, carbohydrates, and fats.[6][7]

Pantothenic acid is the combination of pantoic acid and β-alanine. Its name comes from the Greek πάντοθεν pantothen, meaning "from everywhere", because pantothenic acid, at least in small amounts, is in almost all foods.[6][8][7] Deficiency of pantothenic acid is very rare in humans.[6][7] 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.[1]

  1. ^ a b c d "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". EFSA Journal. 9 (11). Parma, Italy: European Food Safety Authority: 2409. 2011. doi:10.2903/j.efsa.2011.2409.
  2. ^ a b Lide DR, ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  3. ^ a b c "Calcium D-pantothenate". CHEMICALLAND21, AroKor Holdings Inc. Retrieved 5 September 2014.
  4. ^ "MSDS of D-pantothenic acid" (PDF). Human Metabolome Database. Retrieved 5 September 2014.
  5. ^ a b c Leenheer AP, Lambert WE, Bocxlaer JF, eds. (2000). Modern Chromatographic Analysis of Vitamins: Revised And Expanded. Chromatographic Science. Vol. 84 (3rd ed.). Marcel Dekker. p. 533. ISBN 978-0-203-90962-1.
  6. ^ a b c d "Pantothenic acid: Fact Sheet for Health Professionals". Office of Dietary Supplements, US National Institutes of Health. 3 June 2020. Retrieved 27 November 2020.
  7. ^ a b c "Pantothenic acid". Linus Pauling Institute at Oregon State University. Micronutrient Information Center. 1 July 2015. Retrieved 27 November 2020.
  8. ^ Cite error: The named reference usda was invoked but never defined (see the help page).

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