(2R)-2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide

• ChemBase ID: 110974
• Molecular Formular: C9H19NO4
• Molecular Mass: 205.25146
• Monoisotopic Mass: 205.13140809
• SMILES: CC(C)(CO)[C@@H](O)C(=O)NCCCO
• Canonical SMILES: OCCCNC(=O)[C@@H](C(CO)(C)C)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)/t7-/m0/s1
• InChIKey: SNPLKNRPJHDVJA-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
• IUPAC Traditional name: dexpanthenol
• Synonyms: (R)-(+)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide; (R)-2,4-Dihydroxy-3,3-dimethylbutyric 3-hydroxypropylamide; D-Pantothenyl alcohol; Dexpanthenol; Provitamin B; D-PANTOTHENYL ALCOHOL; D-Panthenol; Dexpanthenolum; D-Panthenol; Dexpanthenol; (R)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide; (R)-(+)-2,4-二羟基-N-(3-羟基丙基)-3,3-二甲基丁酰胺; 右旋泛酰醇; 右旋泛醇; 维生素原 B; D-泛醇; D-泛醇; 右旋泛醇

Database IDs

• CAS Number: 81-13-0
• EC Number: 201-327-3
• MDL Number: MFCD00065006
• Beilstein Number: 1724947
• PubChem SID: 24886961; 24887211; 162096984
• PubChem CID: 131204

CALCULATED PROPERTIES

• Acid pKa: 12.68587
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -1.7005135
• LogD (pH = 7.4): -1.7005156
• Log P: -1.7005135
• Molar Refractivity: 51.8848 cm^3
• Polarizability: 20.455023 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Density: 1.20 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.499
• Optical Rotation: [α]20/D +30±1°, c = 5% in H2O

Safety Information

• German water hazard class: 1
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98% (perchloric acid titration); ≥98% (TLC); ≥98.0% (NT); 95+%
• Grade: Ph Eur
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: ≤0.002% heavy metals; ≤0.5% 3-aminopropanol
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C9H19NO4

DETAILS

MP Biomedicals - 05217277

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 76200

Biochem/physiol Actions
D-Panthenol is the alcohol analogue and biological precursor of D-pantothenic acid. These analogues are precursors in the biosynthesis of coenzyme A. D-Panthenol and D-Pantothenic acid are used in a variety of skin protection products. D-pantothenic acid may have a role in controlling keratinocyte proliferation and differentiation. D-Panthenol may be used for studies of skin protection emulsions from UV irradiation and as a humectant.