Panthenol

Pair / mixture of stereoisomers
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 checkY
  • 81-13-0 R checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B00882
Beilstein Reference
 1724945, 1724947 R
ChEBI
  • CHEBI:27373 ☒N
ChEMBL
  • ChEMBL1200979 ☒N
ChemSpider
  • 4516 checkY
  • 115991 R ☒N
  • 4677984 S ☒N
ECHA InfoCard 100.036.839 Edit this at Wikidata
EC Number
  • 240-540-6
KEGG
  • D03726 checkY
  • D00193
MeSH dexpanthenol
PubChem CID
  • 4678
  • 131204 R
  • 5748487 S
RTECS number
  • ES4316500
UNII
  • WV9CM0O67Z checkY
  • 1O6C93RI7Z (R) checkY
CompTox Dashboard (EPA)
  • DTXSID3044598 Edit this at Wikidata
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) checkY
    Key: SNPLKNRPJHDVJA-UHFFFAOYSA-N checkY
  • 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
+29° to +30°
1.499
Pharmacology
A11HA30 (WHO) D03AX03 (WHO), S01XA12 (WHO)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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
1
1
0
Lethal dose or concentration (LD, LC):
10,100 mg kg−1 (intraperitoneal, mouse); 15,000 mg kg−1 (oral, mouse)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

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 cosmetic products as a moisturizer and to improve wound healing.

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,[citation needed] 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] 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).

References

  1. ^ "Dexpanthenol – Compound summary". PubChem Compound. US: National Center for Biotechnology Information. 25 March 2005. Identification. Retrieved 29 June 2012.
  2. ^ a b c Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Bepanthen Creme.
  3. ^ 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.
  4. ^ 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.
  5. ^ a b List PH, Hörhammer L, eds. (1969). Hagers Handbuch der pharmazeutischen Praxis (in German). Vol. 2. Springer. p. 699.
  • v
  • t
  • e
Fat
soluble
A
D
E
K
  • Naphthoquinone
  • Phylloquinone (K1)#
  • Menaquinones (K2)
  • Menadione (K3)‡
  • Various (K4)
  • 4-Amino-2-methyl-1-naphthol (K5)‡
  • 2-Methylnaphthalene-1,4-diamine (K6)
  • 4-Amino-3-methyl-1-naphthol (K7)
Water
soluble
B
C
Combinations
Authority control databases: National Edit this at Wikidata
  • Germany