Panthenol

Panthenol (also called pantothenol) is the alcohol analog of pantothenic acid (vitamin B₅), and is thus a provitamin of B₅. In organisms, it is quickly oxidized to pantothenic acid. It is a viscous transparent liquid at room temperature. Panthenol is used in pharmaceutical and children's products as a moisturizer and to hasten wound healing.

Panthenol

Stereo, skeletal formula of panthenol (R) D-panthenol
Names
Preferred IUPAC name 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide[1]
Other names Pantothenol Pantothenyl alcohol N-Pantoylpropanolamine Bepanthen (trade name) Dexpanthenol (D form)
Identifiers
CAS Number	16485-10-2 Y 81-13-0 R Y
3D model (JSmol)	Interactive image
Beilstein Reference	1724945, 1724947 R
ChEBI	CHEBI:27373 N
ChEMBL	ChEMBL1200979 N
ChemSpider	4516 Y 115991 R N 4677984 S N
ECHA InfoCard	100.036.839
EC Number	240-540-6
KEGG	D03726 Y D00193
MeSH	dexpanthenol
PubChem CID	4678 131204 R 5748487 S
RTECS number	ES4316500
UNII	WV9CM0O67Z Y 1O6C93RI7Z (R) Y
CompTox Dashboard (EPA)	DTXSID3044598
InChI InChI=1S/C9H19NO4/c1-9(2,6-12)7(13)8(14)10-4-3-5-11/h7,11-13H,3-6H2,1-2H3,(H,10,14) Y Key: SNPLKNRPJHDVJA-UHFFFAOYSA-N Y
SMILES CC(C)(CO)C(O)C(=O)NCCCO
Properties
Chemical formula	C9H19NO4
Molar mass	205.254 g·mol−1
Appearance	Highly viscous, colourless liquid
Density	1.2 g mL−1 (at 20 °C)
Melting point	66 to 69 °C (151 to 156 °F; 339 to 342 K) [contradictory]
Boiling point	118 to 120 °C (244 to 248 °F; 391 to 393 K) at 2.7 Pa
log P	−0.989
Acidity (pKa)	13.033
Basicity (pKb)	0.964
Chiral rotation ([α]D)	+29° to +30°
Refractive index (nD)	1.499
Pharmacology
ATC code	A11HA30 (WHO) D03AX03 (WHO), S01XA12 (WHO)
Hazards
NFPA 704 (fire diamond)	1 1 0
Lethal dose or concentration (LD, LC):
LD50 (median dose)	10,100 mg kg−1 (intraperitoneal, mouse); 15,000 mg kg−1 (oral, mouse)
Related compounds
Related compounds	Arginine Theanine Pantothenic acid Hopantenic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Adverse effects

Panthenol is generally well-tolerated. In rare cases, skin irritation causing contact dermatitis and contact allergies have been reported.^[2][3]

Pharmacology

Panthenol readily penetrates into the skin and mucous membranes (including the intestinal mucosa), where it is quickly oxidized to pantothenic acid. Pantothenic acid is extremely hygroscopic.^[4] It is also used in the biosynthesis of coenzyme A, which plays a role in a wide range of enzymatic reactions and in cell growth.^[2][3]

Physical and chemical properties

Dexpanthenol

Panthenol is an odourless, slightly bitter, highly viscous, transparent, and colourless liquid at room temperature,^[5] but salts of pantothenic acid (for example sodium pantothenate) are powders that are typically white. It is easily soluble in water and alcohol, moderately soluble in diethyl ether, soluble in chloroform (1:100),^[5] in propylene glycol, and slightly soluble in glycerin.

Panthenol's expanded chemical formula is HO–CH₂–C(CH₃)₂–CH(OH)–CONH–CH₂CH₂CH₂–OH.

Stereochemistry

Panthenol comes in two enantiomers: D, and L. Only D-panthenol (dexpanthenol) is biologically active, however both forms have moisturizing properties. For cosmetic use, panthenol comes either in D form, or as a racemic mixture of D and L (DL-panthenol).