bis((2E)-but-2-enedioic acid); 2,6-di-tert-butyl-4-[(3-{4-[(3,4,5-trimethoxyphenyl)methyl]piperazin-1-yl}propyl)sulfanyl]phenol

• ChemBase ID: 132937
• Molecular Formular: C39H56N2O12S
• Molecular Mass: 776.93314
• Monoisotopic Mass: 776.35539624
• SMILES: CC(c1c(c(cc(c1)SCCCN1CCN(CC1)Cc1cc(c(c(c1)OC)OC)OC)C(C)(C)C)O)(C)C.C(=C\C(=O)O)/C(=O)O.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.OC(=O)/C=C/C(=O)O.COc1cc(CN2CCN(CC2)CCCSc2cc(c(c(c2)C(C)(C)C)O)C(C)(C)C)cc(c1OC)OC
• InChI: InChI=1S/C31H48N2O4S.2C4H4O4/c1-30(2,3)24-19-23(20-25(28(24)34)31(4,5)6)38-16-10-11-32-12-14-33(15-13-32)21-22-17-26(35-7)29(37-9)27(18-22)36-8;2*5-3(6)1-2-4(7)8/h17-20,34H,10-16,21H2,1-9H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1+
• InChIKey: SPVJPHPGPTVHLT-LVEZLNDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis((2E)-but-2-enedioic acid); 2,6-di-tert-butyl-4-[(3-{4-[(3,4,5-trimethoxyphenyl)methyl]piperazin-1-yl}propyl)sulfanyl]phenol
• IUPAC Traditional name: 2,6-di-tert-butyl-4-[(3-{4-[(3,4,5-trimethoxyphenyl)methyl]piperazin-1-yl}propyl)sulfanyl]phenol; bis(fumaric acid)
• Synonyms: N-[(3,5-Di-tert-butyl-4-hydroxy-1-thiophenyl)]-3-propyl-N′-(2,3,4-trimethoxybenzyl)piperazine difumarate salt; S-15176 difumarate salt

Database IDs

• CAS Number: 148913-55-7
• MDL Number: MFCD11046049
• PubChem SID: 162227214
• PubChem CID: 71308611

CALCULATED PROPERTIES

• H Donor: 1
• LogD (pH = 5.5): 3.7041323
• LogD (pH = 7.4): 5.472812
• Log P: 6.4614153
• Molar Refractivity: 161.1156 cm^3
• Polarizability: 62.763927 Å^3
• Polar Surface Area: 54.4 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false
• Acid pKa: 10.66628
• H Acceptors: 6

PROPERTIES

Physical Property

• Solubility: DMSO: soluble16 mg/mL; H2O: insoluble
• Apperance: solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - S5944

Biochem/physiol Actions
Antioxidant and anti-ischemic agent. Also inhibits mitochondrial permeability transition, prevents the early step in apoptosis by preventing collapse of the electrochemical gradient across the mitochondrial membrane. IC50 for in vitro lipid peroxidation is 0.3 μM. IC50 for carnitine palmitoyltransferase (CPT-1) in heart homogenate is 16.8 μM. The shift from fatty acid to glucose oxidation may contribute to anti-ischemic effect.