 D-panthenol | |
| Names | |
|---|---|
| Preferred IUPAC name 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide[1] | |
Other names
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| Identifiers | |
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3D model (JSmol) | |
| 1724945, 1724947R | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.036.839 |
| EC Number |
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| KEGG | |
| MeSH | dexpanthenol |
| RTECS number |
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| UNII |
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| 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 |
| logP | −0.989 |
| Acidity (pKa) | 13.033 |
| Basicity (pKb) | 0.964 |
Chiral rotation ([α]D) | +29° to +30° |
Refractive index (nD) | 1.499 |
| Pharmacology | |
| A11HA30 (WHO) D03AX03 (WHO),S01XA12 (WHO) | |
| Hazards | |
| NFPA 704 (fire diamond) | |
| 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 | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Panthenol (also calledpantothenol) is thealcoholanalog ofpantothenic acid (vitamin B5), and is thus aprovitamin of B5. In organisms, it is quicklyoxidized to pantothenic acid. It is a viscous transparent liquid at room temperature. Panthenol is used in pharmaceutical and children's products as amoisturizer and to hastenwound healing.
Panthenol is generally well-tolerated. In rare cases, skinirritation causingcontact dermatitis andcontact allergies have been reported.[2][3]
Panthenol readily penetrates into the skin andmucous membranes (including theintestinal mucosa), where it is quickly oxidized to pantothenic acid. Pantothenic acid is extremelyhygroscopic.[4] It is also used in the biosynthesis ofcoenzyme A, which plays a role in a wide range ofenzymatic reactions and in cell growth.[2][3]
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 andalcohol, moderately soluble indiethyl ether, soluble inchloroform (1:100),[5] inpropylene glycol, and slightly soluble inglycerin.
Panthenol's expanded chemical formula is HO–CH2–C(CH3)2–CH(OH)–CONH–CH2CH2CH2–OH.
Panthenol comes in twoenantiomers:D, andL. OnlyD-panthenol (dexpanthenol) is biologically active, however both forms have moisturizing properties. For cosmetic use, panthenol comes either inD form, or as aracemic mixture ofD andL (DL-panthenol).
