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Dexpanthenol Racemic Impurity

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CAS Number
16485-10-2
Synonyms
2,4-Dihydroxy-N- (3-hydroxypropyl) -3,3-dimethylbutanamide
Molecular Formula
C9H19NO4
Molecular Weight
205.3
API Name
Dexpanthenol

Chemical Information

DL-panthenol

Panthenol is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium. Panthenol exists as a racemic mixture containing both the dextrorotatory form (dexpanthenol) and the levorotatory form (levopanthenol). While pantothenic acid is optically active, only the dextrorotatory form ([DB09357]) is biologically active. Dexpanthenol, the active form of panthenol, is enzymatically cleaved to form pantothenic acid (Vitamin B5), which is an essential component of Coenzyme A that acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium. Due to its good penetration and high local concentrations, dexpanthanol is used in many topical products, such as ointments and lotions for treatment of dermatological conditions to relieve itching or promote healing. Dermatological effects of the topical use of dexpanthenol include increased fibroblast proliferation and accelerated re-epithelialization in wound healing. Furthermore, it acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties.

CAS Number16485-10-2
PubChem CID4678
IUPAC Name2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
Molecular FormulaC9H19NO4
Molecular Weight205.25
XLogP-0.9
Topological Polar Surface Area89.8
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Heavy Atom Count14
Formal Charge0
Complexity182
SMILES
CC(C)(CO)C(C(=O)NCCCO)O
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)
InChIKey
SNPLKNRPJHDVJA-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of DL-panthenol
CAS: 16485-10-2
CID: 4678
Formula: C9H19NO4
MW: 205.25
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight205.25
XLogP3-0.9
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Exact Mass205.13140809
Monoisotopic Mass205.13140809
Topological Polar Surface Area89.8 Ų
Heavy Atom Count14
Formal Charge0
Complexity182
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes