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<languages />
{{short description|Pair / mixture of stereoisomers}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 458948255
| ImageFile = Dexpanthenol.svg
| 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
| 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 (chemistry)|alcohol]] [[Analog (chemistry)|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==
[[File:Bepanthen® — BAYER — Augen- und Nasensalbe (Dexpanthenol) mit Verpackung und Beipackzettel — Deutschland.jpg|thumb|left|Bepanthen eye and nose ointment (Germany)]]
In pharmaceuticals, cosmetics, and personal-care products, panthenol is a moisturizer and [[humectant]], used in [[ointment]]s, lotions, shampoos, nasal sprays, eye drops, [[throat lozenge|lozenge]]s, and cleaning solutions for contact lenses.

In ointments it is used for the treatment of [[sunburn]]s, mild [[burn (injury)|burns]], minor skin injuries, and disorders (in concentrations of up to 2–5%). It improves [[tissue hydration|hydration]], reduces itching and inflammation of the skin, improves skin elasticity, and accelerates [[Epidermis (skin)|epidermal]] wounds' rate of healing. For this purpose, it is sometimes combined with [[allantoin]].

It binds to the hair shaft readily, so, it is a common component of commercial [[shampoo]]s and [[hair conditioner]]s (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 allergy|contact allergies]] have been reported.

==Pharmacology==
Panthenol readily penetrates into the skin and [[mucous membrane]]s (including the [[intestinal mucosa]]), where it is quickly oxidized to pantothenic acid. Pantothenic acid is extremely [[hygroscopic]]. It is also used in the biosynthesis of [[coenzyme A]], which plays a role in a wide range of [[enzyme|enzymatic]] reactions and in cell growth.

==Physical and chemical properties==
[[File:Dexpanthenol viscosity.jpg|thumb|left|Dexpanthenol]]
Panthenol is an odourless, slightly bitter, highly viscous, transparent, and colourless liquid at room temperature, but salts of pantothenic acid (for example sodium pantothenate) are powders that are typically white. It is easily soluble in water and [[ethanol|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 [[enantiomer]]s: 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).

{{vitamin}}
{{preparations for treatment of wounds and ulcers}}

{{二次利用|date=17 December 2023}}
[[Category:B vitamins]]
[[Category:Alcohols]]
[[Category:Hairdressing]]
[[Category:Cosmetics chemicals]]
[[Category:Carboxamides]]
[[Category:Ophthalmology drugs]]

Panthenol/en - Revision history

FuzzyBot: Updating to match new version of source page