Panthenol

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Panthenol
Stereo, skeletal formula of panthenol (R)
Identifiers
CAS number 16485-10-2 N, 81-13-0 R YesY
PubChem 4678, 131204 R, 5748487 S
ChemSpider 4516 YesY, 115991 R YesY, 4677984 S YesY
UNII 1O6C93RI7Z YesY
EC number 240-540-6
KEGG D03726 YesY
MeSH dexpanthenol
ChEBI CHEBI:27373 N
ChEMBL CHEMBL1200979 N
RTECS number ES4316500
ATC code A11HA30,D03AX03, S01XA12
Beilstein Reference 1724945, 1724947 R
3DMet B00882
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C9H19NO4
Molar mass 205.25 g mol−1
Appearance Colourless liquid[contradictory]
Density 1.2 g mL−1 (at 20 °C)
Melting point 66 to 69 °C (151 to 156 °F; 339 to 342 K)
log P −0.989
Acidity (pKa) 13.033
Basicity (pKb) 0.964
Refractive index (nD) 1.499
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
LD50 10,100 mg kg−1 (intraperitoneal, mouse); 15,000 mg kg−1 (oral, mouse)
Related compounds
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Panthenol (pantothenol) is the alcohol analog of pantothenic acid (vitamin B5), and is thus a provitamin of B5. In organisms it is quickly oxidized to pantothenate. Panthenol is a highly viscous transparent liquid at room temperature, but salts of pantothenic acid (for example sodium pantothenate) are powders (typically white). It is soluble in water, alcohol and propylene glycol, soluble in ether and chloroform, and slightly soluble in glycerin.

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).

Panthenol's expanded chemical formula is: HO-CH2-C(CH3)2-CH(OH)-CONH-CH2CH2CH2-OH.

Uses[edit]

Bepanthen eye and nose lotion (Germany)

In cosmetics and personal-care products, panthenol is a humectant, emollient, and moisturizer. It binds to the hair shaft readily; so, it is a common component of commercial shampoos and hair conditioners (in concentrations of 0.1-1.0%). 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 many tattoo artists as a post-tattooing moisturising cream.

Panthenol draws moisture from the atmosphere and readily binds to water molecules. When applied to the hair panthenol will help to moisturize it and give it a shine and gloss. For this reason it has become a very popular ingredient in shampoos and conditioners.

In ointments, panthenol is an effective skin penetrator.[2] It is sometimes mixed with allantoin, in concentrations of up to 2-5%, and is used for treatment of sunburns, mild burns and minor skin disorders.[citation needed] It improves hydration, reduces itching and inflammation of the skin, and accelerates epidermal wounds' rate of healing.[2]

If ingested, panthenol is metabolized to pantothenic acid.

Synonyms[edit]

Dexpanthol

Other names for panthenol include:

  • Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (R)-
  • Butyramide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, D-(+)-
  • Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (2R)-
  • D-Panthenol
  • Dexpanthenol (DCIR)
  • Dexpanthenolum
  • Propanolamine, N-pantoyl-
  • d-Pantothenyl alcohol
  • Bepanthen

References[edit]

  1. ^ "dexpanthenol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identificaion. Retrieved 29 June 2012. 
  2. ^ a b Ebner F, Heller A, Rippke F, Tausch I (2002). "Topical Use of Dexpanthenol in Skin Disorders". American Journal of Clinical Dermatology 3 (6): 427–433. doi:10.2165/00128071-200203060-00005. PMID 12113650. 

External links[edit]