2-(tetradecylsulfanyl)acetic acid

• ChemBase ID: 129778
• Molecular Formular: C16H32O2S
• Molecular Mass: 288.48908
• Monoisotopic Mass: 288.21230126
• SMILES: O=C(O)CSCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCSCC(=O)O
• InChI: InChI=1S/C16H32O2S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-19-15-16(17)18/h2-15H2,1H3,(H,17,18)
• InChIKey: IPBCWPPBAWQYOO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(tetradecylsulfanyl)acetic acid
• IUPAC Traditional name: (tetradecylsulfanyl)acetic acid
• Synonyms: TTA; Tetradecylthioacetic acid; 1-(Carboxymethylthio)tetradecane; Tetradecylthioacetic acid; 1-Mono(carboxymethylthio)tetradecane

Database IDs

• CAS Number: 2921-20-2
• MDL Number: MFCD00128230
• PubChem SID: 162224066; 24278726
• PubChem CID: 114924
• Chemspider ID: 102869
• Wikipedia Title: Tetradecylthioacetic_acid

CALCULATED PROPERTIES

• Acid pKa: 4.5831404
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.0905914
• LogD (pH = 7.4): 3.3154533
• Log P: 6.0560365
• Molar Refractivity: 85.0567 cm^3
• Polarizability: 33.774998 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble ≥22 mg/mL; Ethanol
• Apperance: white; White Solid
• Melting Point: 63-66°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... PPARA(5465)

Product Information

• Purity: ≥97% (NMR)
• Linear Formula: C14H29-S-CH2COOH

DETAILS

Sigma Aldrich - T1698

Biochem/physiol Actions
PPARα agonist; activation in ranking order: PPARδ > PPARα > PPARγ
Packaging
Packaged under nitrogen.

Toronto Research Chemicals - T292625

TTA is a novel thio-fatty acid which cannot undergo beta-oxidation. It induces apoptosis in IPC-81 leukemia cells via depolarization of mitochondrial membrane potential and inhibits glioma cell proliferation. TTA completely prevents high fat diet-induce

REFERENCES

• Madsen, L., et al.: J. Lipid Res., 43, 742 (2002)
• Kronstad, K.J., et al.: Chem. Biol., 10, 609 (2003, Berge, K., et al.: J. Lipid Res., 44, 118 (2002)