Panthenol: Difference between revisions

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Created page with "{{short description|Pair / mixture of stereoisomers}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 458948255 | ImageFile = Dexpanthenol.svg | ImageCaption = <small>D</small>-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|'..."
 
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'''Panthenol''' (also called '''pantothenol''') is the [[Alcohol (chemistry)|alcohol]] [[Analog (chemistry)|analog]] of [[pantothenic acid]] (vitamin B<sub>5</sub>), and is thus a [[provitamin]] of B<sub>5</sub>. 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.
'''Panthenol''' (also called '''pantothenol''') is the [[Alcohol (chemistry)|alcohol]] [[Analog (chemistry)|analog]] of [[pantothenic acid]] (vitamin B<sub>5</sub>), and is thus a [[provitamin]] of B<sub>5</sub>. 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==
==Uses== <!--T:3-->
[[File:Bepanthen® — BAYER — Augen- und Nasensalbe (Dexpanthenol) mit Verpackung und Beipackzettel — Deutschland.jpg|thumb|left|Bepanthen eye and nose ointment (Germany)]]
[[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 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.


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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]].
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]].


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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 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.


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It is also recommended by [[tattoo]] artists as a post-tattooing moisturising cream.
It is also recommended by [[tattoo]] artists as a post-tattooing moisturising cream.


==Adverse effects==
==Adverse effects== <!--T:7-->
Panthenol is generally well tolerated. In rare cases, skin irritation and [[contact allergy|contact allergies]] have been reported.
Panthenol is generally well tolerated. In rare cases, skin irritation and [[contact allergy|contact allergies]] have been reported.


==Pharmacology==
==Pharmacology== <!--T:8-->
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.
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==
==Physical and chemical properties== <!--T:9-->
[[File:Dexpanthenol viscosity.jpg|thumb|left|Dexpanthenol]]
[[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 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]].


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Panthenol's expanded chemical formula is HO–CH<sub>2</sub>–C(CH<sub>3</sub>)<sub>2</sub>–CH(OH)–CONH–CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>–OH.
Panthenol's expanded chemical formula is HO–CH<sub>2</sub>–C(CH<sub>3</sub>)<sub>2</sub>–CH(OH)–CONH–CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>–OH.


===Stereochemistry===
===Stereochemistry=== <!--T:11-->
Panthenol comes in two [[enantiomer]]s: <small>D,</small> and <small>L</small>. Only <small>D</small>-panthenol (dexpanthenol) is biologically active, however both forms have moisturizing properties. For cosmetic use, panthenol comes either in <small>D</small> form, or as a [[racemic]] mixture of <small>D</small> and <small>L</small> (<small>DL</small>-panthenol).
Panthenol comes in two [[enantiomer]]s: <small>D,</small> and <small>L</small>. Only <small>D</small>-panthenol (dexpanthenol) is biologically active, however both forms have moisturizing properties. For cosmetic use, panthenol comes either in <small>D</small> form, or as a [[racemic]] mixture of <small>D</small> and <small>L</small> (<small>DL</small>-panthenol).


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


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{{二次利用|date=17 December 2023}}
{{二次利用|date=17 December 2023}}
[[Category:B vitamins]]
[[Category:B vitamins]]
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[[Category:Carboxamides]]
[[Category:Carboxamides]]
[[Category:Ophthalmology drugs]]
[[Category:Ophthalmology drugs]]
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Latest revision as of 15:11, 3 April 2024

Other languages:
Panthenol
Stereo, skeletal formula of panthenol (R)
D-panthenol
Names
Preferred IUPAC name
2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
Other names
  • Pantothenol
  • Pantothenyl alcohol
  • N-Pantoylpropanolamine
  • Bepanthen (trade name)
  • Dexpanthenol (D form)
Identifiers
3D model (JSmol)
3DMet
1724945, 1724947 R
ChEBI
ChEMBL
ChemSpider
EC Number
  • 240-540-6
KEGG
MeSH dexpanthenol
RTECS number
  • ES4316500
UNII
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)
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

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%). It improves hydration, reduces itching and inflammation of the skin, improves skin elasticity, and accelerates 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 shampoos and hair conditioners (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 allergies have been reported.

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. 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.

Physical and chemical properties

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 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).

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