4-{[4-(morpholin-4-yl)butyl]sulfanyl}phenol

• ChemBase ID: 153275
• Molecular Formular: C14H21NO2S
• Molecular Mass: 267.38704
• Monoisotopic Mass: 267.12929992
• SMILES: c1cc(ccc1O)SCCCCN1CCOCC1
• Canonical SMILES: Oc1ccc(cc1)SCCCCN1CCOCC1
• InChI: InChI=1S/C14H21NO2S/c16-13-3-5-14(6-4-13)18-12-2-1-7-15-8-10-17-11-9-15/h3-6,16H,1-2,7-12H2
• InChIKey: YHKNLUTUXZDOQI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[4-(morpholin-4-yl)butyl]sulfanyl}phenol
• IUPAC Traditional name: 4-{[4-(morpholin-4-yl)butyl]sulfanyl}phenol
• Synonyms: 33N14; 4-(4-Morpholinobutylthio)phenol; MoTP

Database IDs

• CAS Number: 57055-82-0
• MDL Number: MFCD00642470
• PubChem SID: 162247414
• PubChem CID: 3096300

CALCULATED PROPERTIES

• Acid pKa: 9.407041
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.7218366
• LogD (pH = 7.4): 2.2892082
• Log P: 2.5715861
• Molar Refractivity: 77.4506 cm^3
• Polarizability: 30.196272 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥80 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H21NO2S

DETAILS

Sigma Aldrich - SML0047

Biochem/physiol Actions
MoTP (also known as 33N14) reversibly blocks the specification of neural crest cells into melanocytes in zebrafish studies. Differentiation of neural crest cell-derived melanoblasts proceeds to late developmental stages, but they fail to reach the terminal stage of melanin production and die. Melanocytotoxicity is dependent on tyrosinase activity which convert it into a toxic form. MoTP specifically ablates only cells that express tyrosinase at high levels, which in the embryo are limited to melanoblasts and newly formed melanocytes. MoTP should be a useful tool for elucidating melanocyte stem cell regeneration, recruitment, and maintenance.