2,6-di-tert-butyl-4-({2-[(3,5-di-tert-butyl-4-hydroxyphenyl)sulfanyl]propan-2-yl}sulfanyl)phenol

• ChemBase ID: 1376
• Molecular Formular: C31H48O2S2
• Molecular Mass: 516.84162
• Monoisotopic Mass: 516.30957278
• SMILES: S(c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1)C(Sc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1)(C)C
• Canonical SMILES: CC(Sc1cc(c(c(c1)C(C)(C)C)O)C(C)(C)C)(Sc1cc(c(c(c1)C(C)(C)C)O)C(C)(C)C)C
• InChI: InChI=1S/C31H48O2S2/c1-27(2,3)21-15-19(16-22(25(21)32)28(4,5)6)34-31(13,14)35-20-17-23(29(7,8)9)26(33)24(18-20)30(10,11)12/h15-18,32-33H,1-14H3
• InChIKey: FYPMFJGVHOHGLL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,6-di-tert-butyl-4-({2-[(3,5-di-tert-butyl-4-hydroxyphenyl)sulfanyl]propan-2-yl}sulfanyl)phenol
• IUPAC Traditional name: probucol
• Brand Name: Biphenabid; Bisbid; Bisphenabid; Lesterol; Lorelco; Lursell; Lurselle; Panavir; Sinlestal
• Synonyms: 4,4'- (Isopropylidenedithio)bis(2, 6-di-tert-butylphenol); 4,4'-(Isopropylidenedithio)bis(2, 6-di-tert-butylphenol); 4,4'-(Isopropylidenedithio)bis(2,6-di-tert-butylphenol); 4,4'-(Isopropylidenedithio)bis[2, 6-di-tert-butylphenol]; Acetone bis(3,5-di-tert-butyl-4-hydroxyphenyl) mercaptole; Acetone, bis (3,5-di-tert-butyl-4-hydroxyphenyl) mercaptole; Acetone, bis(3,5-di-tert-butyl-4-hydroxyphenyl) mercaptole; Probucolum [inn-latin]; Probucol; Probucol; 4,4'-[(1-Methylethylidene)bis(thio)]bis-[2,6-bis(1,1-dimethylethyl)phenol]; 4,4'-(isopropylidenedithio)bis[2,6-di-tert-butylphenol]; 4,4'-[(1-Methylethylidene)bis(thio)]bis[2,6-bis(1,1-dimethylethyl)phenol; Bis(3,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole Acetone; 4,4'-(Isopropylidenedithio)bis[2,6-di-tert-butyl-phenol; Biphenabid; Bisbid; Bisphenabid; DH 581; Lipomal; Lorelco; Lurselle; NSC 652160; NSC 86225; 普罗布考

Database IDs

• CAS Number: 23288-49-5
• EC Number: 245-560-9
• MDL Number: MFCD00079281
• PubChem SID: 160964836; 46508876; 24899054
• PubChem CID: 4912

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.290911
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 10.569517
• LogD (pH = 7.4): 10.568969
• Log P: 10.569524
• Molar Refractivity: 159.259 cm^3
• Polarizability: 61.9502 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 8.92
• LOG S: -7.09
• Solubility (Water): 4.18e-05 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 124-126°C; 126-128°C

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: AL3705000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others
• Gene Information: human ... IL1B(3553), IL6(3569), TNF(7124)

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB01599

• Drug Groups: approved
• Description: A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).
• Indication: Used to lower LDL and HDL cholesterol.
• Pharmacology: Probucol lowers the level of cholesterol in the bloodstream by increasing the rate of LDL catabolism. Additionally, probucol may inhibit cholesterol synthesis and delay cholesterol absorption. Probucol is a powerful antioxidant drug normally used to prevent vascular disease caused by the free radicals in the body.
• Affected Organisms: Humans and other mammals
• Absorption: Absorption from the gastrointestinal tract is limited and variable (about 7%).
• Half Life: Ranges from 12 hours to more than 500 hours, the longest half-life probably being in adipose tissue.
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - P9672

Biochem/physiol Actions
提高 HDL 相关胆固醇酯的选择性摄取

Toronto Research Chemicals - P755100

Probucol is an antilipemic.

REFERENCES

• Shakir, D., et al.: J. Clin. Med. Res., 1, 8 (2009)
• Kubo, Y., et al.: Biol. Pharm. Bull., 32, 1880 (2009)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)