Pantothenic acid

Pantothenic acid
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
CAS Number	599-54-2 ; 79-83-4 (R) ;
3D model (JSmol)	Interactive image; (R): Interactive image; (S): Interactive image;
3DMet	B00193;
Beilstein Reference	1727062, 1727064 (R)
ChEBI	CHEBI:7916 ;
ChEMBL	ChEMBL1594 ;
ChemSpider	963 ; 6361 (R) ; 4677898 (S) ;
DrugBank	DB01783 ;
ECHA InfoCard	100.009.061
EC Number	209-965-4;
KEGG	D07413 ;
MeSH	Pantothenic+Acid
PubChem CID	988; 6613 (R); 5748353 (S);
RTECS number	RU4729000;
UNII	66Y94D1203 ; 19F5HK2737 (R) ;
CompTox Dashboard (EPA)	DTXSID7047229 ;
	InChI 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) Key: GHOKWGTUZJEAQD-UHFFFAOYSA-N ;
	SMILES 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
Chemical formula	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)
Melting point	183.833 °C (362.899 °F; 456.983 K) ; 196–200 °C (385–392 °F; 469–473 K); decomposes (Ca2+ salt)
Solubility in water	Very soluble; 2.11 g/mL (Ca2+ salt)
Solubility	Very soluble in C6H6, ether; Ca2+ salt:; Slightly soluble in alcohol, CHCl3
log P	−1.416
Acidity (pKa)	4.41
Basicity (pKb)	9.698
Chiral rotation ([α]D)	+37.5°; +24.3° (Ca2+ salt)
Hazards
NFPA 704 (fire diamond)	2 1 0
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	> 10 mg/g (Ca2+ salt)
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). verify (what is ?) Infobox references

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]

^ ^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.
^ ^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.
^ ^a ^b ^c "Calcium D-pantothenate". CHEMICALLAND21, AroKor Holdings Inc. Retrieved 5 September 2014.
^ "MSDS of D-pantothenic acid" (PDF). Human Metabolome Database. Retrieved 5 September 2014.
^ ^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.
^ ^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.
^ ^a ^b ^c "Pantothenic acid". Linus Pauling Institute at Oregon State University. Micronutrient Information Center. 1 July 2015. Retrieved 27 November 2020.
^ Cite error: The named reference usda was invoked but never defined (see the help page).

[eu-1] "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.

[crc-2] Lide DR, ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.

[chemicalland-3] "Calcium D-pantothenate". CHEMICALLAND21, AroKor Holdings Inc. Retrieved 5 September 2014.

[hmdbsa-4] "MSDS of D-pantothenic acid" (PDF). Human Metabolome Database. Retrieved 5 September 2014.

[mod-5] 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.

[ods-6] "Pantothenic acid: Fact Sheet for Health Professionals". Office of Dietary Supplements, US National Institutes of Health. 3 June 2020. Retrieved 27 November 2020.

[lpi-7] "Pantothenic acid". Linus Pauling Institute at Oregon State University. Micronutrient Information Center. 1 July 2015. Retrieved 27 November 2020.

[usda-8] Cite error: The named reference usda was invoked but never defined (see the help page).

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