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Wikipedia

Panthenol

January 01, 1970

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.

Panthenol

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
  • 16485-10-2 Y
  • 81-13-0 R Y
3D model (JSmol)
  • Interactive image
3DMet
  • B00882
1724945, 1724947 R
ChEBI
  • CHEBI:27373 N
ChEMBL
  • ChEMBL1200979 N
ChemSpider
  • 4516 Y
  • 115991 R N
  • 4677984 S N
ECHA InfoCard 100.036.839
EC Number
  • 240-540-6
KEGG
  • D03726 Y
  • D00193
MeSH dexpanthenol
  • 4678
  • 131204 R
  • 5748487 S
RTECS number
  • ES4316500
UNII
  • WV9CM0O67Z Y
  • 1O6C93RI7Z (R) Y
  • DTXSID3044598
  • 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)
Health 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 ?)

Uses edit

 
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%).[2] It improves hydration, reduces itching and inflammation of the skin, improves skin elasticity, and accelerates epidermal wounds' rate of healing.[3] 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,[citation needed] 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 edit

Panthenol is generally well tolerated. In rare cases, skin irritation and contact allergies have been reported.[2][3]

Pharmacology edit

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 edit

 
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 edit

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 edit

  1. ^ "Dexpanthenol – Compound summary". PubChem Compound. US: National Center for Biotechnology Information. 25 March 2005. Identification. Retrieved 29 June 2012.
  2. ^ a b c Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Bepanthen Creme.
  3. ^ a b c Ebner F, Heller A, Rippke F, Tausch I (2002). "Topical use of dexpanthenol in skin disorders". American Journal of Clinical Dermatology. 3 (6): 427–33. doi:10.2165/00128071-200203060-00005. PMID 12113650. S2CID 35836478.
  4. ^ Dinnendahl V, Fricke U, eds. (1991). Arzneistoff-Profile (in German). Vol. 7 (8 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. Pantothensäure. ISBN 978-3-7741-9846-3.
  5. ^ a b List PH, Hörhammer L, eds. (1969). Hagers Handbuch der pharmazeutischen Praxis (in German). Vol. 2. Springer. p. 699.

January 01, 1970
panthenol, also, called, pantothenol, alcohol, analog, pantothenic, acid, vitamin, thus, provitamin, organisms, quickly, oxidized, pantothenic, acid, viscous, transparent, liquid, room, temperature, used, pharmaceutical, cosmetic, products, moisturizer, improv. 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 Panthenol D panthenol Names Preferred IUPAC name 2 4 Dihydroxy N 3 hydroxypropyl 3 3 dimethylbutanamide 1 Other names PantothenolPantothenyl alcoholN PantoylpropanolamineBepanthen trade name Dexpanthenol D form Identifiers CAS Number 16485 10 2 Y81 13 0 R Y 3D model JSmol Interactive image 3DMet B00882 Beilstein Reference 1724945 1724947 R ChEBI CHEBI 27373 N ChEMBL ChEMBL1200979 N ChemSpider 4516 Y115991 R N4677984 S N ECHA InfoCard 100 036 839 EC Number 240 540 6 KEGG D03726 YD00193 MeSH dexpanthenol PubChem CID 4678131204 R5748487 S RTECS number ES4316500 UNII WV9CM0O67Z Y1O6C93RI7Z R Y CompTox Dashboard EPA DTXSID3044598 InChI 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 YKey SNPLKNRPJHDVJA UHFFFAOYSA N Y SMILES CC C CO C O C O NCCCO Properties Chemical formula C 9H 19N O 4 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 Chiral rotation a D 29 to 30 Refractive index nD 1 499 Pharmacology ATC code A11HA30 WHO D03AX03 WHO S01XA12 WHO Hazards NFPA 704 fire diamond 110 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 ArginineTheaninePantothenic acidHopantenic acid Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Uses 2 Adverse effects 3 Pharmacology 4 Physical and chemical properties 4 1 Stereochemistry 5 ReferencesUses edit nbsp 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 2 It improves hydration reduces itching and inflammation of the skin improves skin elasticity and accelerates epidermal wounds rate of healing 3 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 citation needed 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 editPanthenol is generally well tolerated In rare cases skin irritation and contact allergies have been reported 2 3 Pharmacology editPanthenol 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 edit nbsp 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 edit 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 edit Dexpanthenol Compound summary PubChem Compound US National Center for Biotechnology Information 25 March 2005 Identification Retrieved 29 June 2012 a b c Haberfeld H ed 2015 Austria Codex in German Vienna Osterreichischer Apothekerverlag Bepanthen Creme a b c Ebner F Heller A Rippke F Tausch I 2002 Topical use of dexpanthenol in skin disorders American Journal of Clinical Dermatology 3 6 427 33 doi 10 2165 00128071 200203060 00005 PMID 12113650 S2CID 35836478 Dinnendahl V Fricke U eds 1991 Arzneistoff Profile in German Vol 7 8 ed Eschborn Germany Govi Pharmazeutischer Verlag Pantothensaure ISBN 978 3 7741 9846 3 a b List PH Horhammer L eds 1969 Hagers Handbuch der pharmazeutischen Praxis in German Vol 2 Springer p 699 Retrieved from https en wikipedia org w index php title Panthenol amp oldid 1190308557, wikipedia, wiki, book, books, library,

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