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 as a moisturizer and to improve wound healing in pharmaceutical and cosmetic products.

Panthenol

Names
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 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
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)
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).
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Infobox references

Uses

Bepanthen eye and nose ointment (Germany)

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 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; so, 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, lubricating the hair shaft and giving it a shiny appearance.

It is also recommended by tattoo artists as a post-tattooing moisturising cream.

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,[4] that is, it binds water effectively. It is also used in the biosynthesis of coenzyme A, which plays a role in a wide range of enzymatic reactions and thus 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 (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).

References

1. "Dexpanthenol – Compound summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification. Retrieved 29 June 2012.
2. Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Bepanthen Creme.
3. 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.
4. Dinnendahl V, Fricke U, eds. (1991). Arzneistoff-Profile (in German). 7 (8 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. Pantothensäure. ISBN 978-3-7741-9846-3.
5. List PH, Hörhammer L, eds. (1969). Hagers Handbuch der pharmazeutischen Praxis (in German). 2. Springer. p. 699.