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Panthenol
	; D-panthenol
Names
	Preferred IUPAC name 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
	Other names Pantothenol; Pantothenyl alcohol; N-Pantoylpropanolamine; Bepanthen (trade name); Dexpanthenol (D form);
Identifiers
CAS Number	16485-10-2 ; 81-13-0 R ;
3D model (JSmol)	Interactive image;
3DMet	B00882;
Beilstein Reference	1724945, 1724947 R
ChEBI	CHEBI:27373 ;
ChEMBL	ChEMBL1200979 ;
ChemSpider	4516 ; 115991 R ; 4677984 S ;
ECHA InfoCard	100.036.839
EC Number	240-540-6;
KEGG	D03726 ; D00193;
MeSH	dexpanthenol
PubChem CID	4678; 131204 R; 5748487 S;
RTECS number	ES4316500;
UNII	WV9CM0O67Z ; 1O6C93RI7Z (R) ;
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) Key: SNPLKNRPJHDVJA-UHFFFAOYSA-N ;
	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). verify (what is ?) Infobox references

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.

Uses

In pharmaceuticals, cosmetics, and personal-care products, panthenol is a moisturizer and humectant, used in ointments, lotions, shampoos, nasal sprays, eye drops, lozenges, and cleaning solutions for contact lenses.

In ointments it is used for the treatment of sunburns, mild burns, minor skin injuries, and skin disorders (in concentrations of up to 2–5%).^[2] It improves hydration, reduces itching and inflammation of the skin, improves skin elasticity, and accelerates epidermal wounds' rate of healing.^[3] For this purpose, it is sometimes combined with allantoin.

It binds to the hair shaft readily, due to which it is a common component of commercial shampoos and hair conditioners (in concentrations of 0.1–1%). It coats the hair and seals its surface,^{[citation needed]} lubricating the hair shaft and giving it a shiny appearance.

D-panthenol (dexpanthenol) is sometimes used as an ingredient in tattoo aftercare products, with one study finding it can assist in wound care and tattoo preservation.^[4]

Adverse effects

Panthenol is generally well tolerated. In rare cases, skin irritation 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.^[5] 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

Panthenol is an odourless, slightly bitter, highly viscous, transparent, and colourless liquid at room temperature,^[6] 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),^[6] 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).

References

^ "Dexpanthenol – Compound summary". PubChem Compound. US: National Center for Biotechnology Information. 25 March 2005. Identification. Retrieved 29 June 2012.
^ ^a ^b ^c Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Bepanthen Creme.
^ ^a ^b ^c Ebner F, Heller A, Rippke F, Tausch I (2002). "Topical use of dexpanthenol in skin disorders". American Journal of Clinical Dermatology. 3 (6): 427–33. doi:10.2165/00128071-200203060-00005. PMID 12113650. S2CID 35836478.
^ Schmid, Daphné A.; Domingues, Marisa P.; Nanu, Alina; Kluger, Nicolas; de Salvo, Raffaella; Trapp, Sonja (2022). "Exploratory evaluation of tolerability, performance, and cosmetic acceptance of dexpanthenol-containing dermo-cosmetic wash and sun-care products for tattoo aftercare". Health Science Reports. 5 (4): e635. doi:10.1002/hsr2.635. ISSN 2398-8835. PMC 9235347. PMID 35782304. The 2.5% dexpanthenol‐containing wash demonstrated to be suitable for mild effective cleansing of fresh tattoos to complement standard tattoo aftercare with a dexpanthenol‐containing ointment. ... In the current study, 2.5% dexpanthenol‐containing sun‐care SPF50+ cream was demonstrated to maintain the esthetic appearance of existing tattoos by preserving vibrant colors and preventing fading of the tattoos, while it was easy to apply and keeping the tattooed skin smooth and hydrated. Assessment of the skin barrier function showed a decrease in TEWL, or outward diffusion of water through the skin, after 28 days of daily application, an observation which confirms the ability of the 2.5% dexpanthenol‐containing sun‐care SPF50+ cream to maintain the skin barrier and prevent the drying out of tattooed skin in addition to providing protection against UV radiation.
^ Dinnendahl V, Fricke U, eds. (1991). Arzneistoff-Profile (in German). Vol. 7 (8 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. Pantothensäure. ISBN 978-3-7741-9846-3.
^ ^a ^b List PH, Hörhammer L, eds. (1969). Hagers Handbuch der pharmazeutischen Praxis (in German). Vol. 2. Springer. p. 699.