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Panthenol

Pair / mixture of stereoisomers From Wikipedia, the free encyclopedia

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.

Quick Facts Names, Identifiers ...
Panthenol
Thumb
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
3D model (JSmol)
1724945, 1724947 R
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.036.839
EC Number
  • 240-540-6
KEGG
MeSH dexpanthenol
RTECS number
  • ES4316500
UNII
  • 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
  • CC(C)(CO)C(O)C(=O)NCCCO
Properties
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)
ThumbHealth 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 YN ?)
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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

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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

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