panthenol
{{short description|Pair / mixture of stereoisomers}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 458948255
| ImageFile = Dexpanthenol.svg
| ImageClass = skin-invert-image
| ImageCaption = D-panthenol
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 160
| ImageName = Stereo, skeletal formula of panthenol (R)
| PIN = 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide{{cite web|title=Dexpanthenol – Compound summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4678&loc=ec_rcs#x291|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=29 June 2012|location=US|date=25 March 2005|at=Identification}}
| OtherNames = {{unbulleted list|Pantothenol|Pantothenyl alcohol|N-Pantoylpropanolamine|Bepanthen (trade name)|Dexpanthenol (D form)
}}
|Section1={{Chembox Identifiers
| CASNo = 16485-10-2
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1 = 81-13-0
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1_Comment = R
| PubChem = 4678
| PubChem1 = 131204
| PubChem1_Comment = R
| PubChem2 = 5748487
| PubChem2_Comment = S
| ChemSpiderID = 4516
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1 = 115991
| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1_Comment = R
| ChemSpiderID2 = 4677984
| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID2_Comment = S
| UNII = WV9CM0O67Z
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = 1O6C93RI7Z
| UNII1_Comment = (R)
| EINECS = 240-540-6
| KEGG = D03726
| KEGG2 = D00193
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = dexpanthenol
| ChEBI = 27373
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1200979
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| RTECS = ES4316500
| Beilstein = 1724945, 1724947 R
| 3DMet = B00882
| SMILES = CC(C)(CO)C(O)C(=O)NCCCO
| StdInChI = 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)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SNPLKNRPJHDVJA-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=9 | H=19 | N=1 | O=4
| Appearance = Highly viscous, colourless liquid
| Density = 1.2 g mL−1 (at 20 °C)
| BoilingPtC = 118 to 120
| BoilingPt_notes = at 2.7 Pa
| MeltingPtC = 66 to 69
| MeltingPt_notes = {{contradict-inline|reason=is a viscous liquid at room temperature|date=July 2016}}
| LogP = −0.989
| pKa = 13.033
| pKb = 0.964
| RefractIndex = 1.499
| SpecRotation = +29° to +30°
}}
|Section6={{Chembox Pharmacology
| ATCCode_prefix = A11
| ATCCode_suffix = HA30
| ATC_Supplemental = {{aTC|D03|AX03}}, {{aTC|S01|XA12}}
}}
|Section7={{Chembox Hazards
| LD50 = 10,100 mg kg−1 (intraperitoneal, mouse); 15,000 mg kg−1 (oral, mouse)
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
}}
|Section8={{Chembox Related
| OtherCompounds = {{unbulleted list|Arginine|Theanine|Pantothenic acid|Hopantenic acid}}
}}
}}
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.
Adverse effects
Panthenol is generally well tolerated. In rare cases, skin irritation and contact allergies have been reported.{{cite journal | vauthors = Ebner F, Heller A, Rippke F, Tausch I | title = Topical use of dexpanthenol in skin disorders | journal = American Journal of Clinical Dermatology | volume = 3 | issue = 6 | pages = 427–33 | year = 2002 | pmid = 12113650 | doi = 10.2165/00128071-200203060-00005 | s2cid = 35836478 }}
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.{{cite book|title=Arzneistoff-Profile| veditors = Dinnendahl V, Fricke U |publisher=Govi Pharmazeutischer Verlag|location=Eschborn, Germany|date=1991|edition=8|volume=7|at=Pantothensäure|isbn=978-3-7741-9846-3|language=German}} 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.{{cite book|title=Austria-Codex| veditors = Haberfeld H |at=Bepanthen Creme|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2015|language=German}}
Physical and chemical properties
File:Dexpanthenol viscosity.jpg
Panthenol is an odourless, slightly bitter, highly viscous, transparent, and colourless liquid at room temperature,{{cite book|title=Hagers Handbuch der pharmazeutischen Praxis| veditors = List PH, Hörhammer L |volume=2|page=699|publisher=Springer|language=de|year=1969}} 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), 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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{{vitamin}}
{{preparations for treatment of wounds and ulcers}}
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