4-[(3R,4S)-4-(4-hydroxyphenyl)hexan-3-yl]phenol

• ChemBase ID: 5561
• Molecular Formular: C18H22O2
• Molecular Mass: 270.36608
• Monoisotopic Mass: 270.16197994
• SMILES: c1c(ccc(c1)[C@H](CC)[C@H](CC)c1ccc(O)cc1)O
• Canonical SMILES: CC[C@H]([C@@H](c1ccc(cc1)O)CC)c1ccc(cc1)O
• InChI: InChI=1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3/t17-,18+
• InChIKey: PBBGSZCBWVPOOL-HDICACEKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(3R,4S)-4-(4-hydroxyphenyl)hexan-3-yl]phenol; 4-[(3S,4R)-4-(4-hydroxyphenyl)hexan-3-yl]phenol
• IUPAC Traditional name: hexestrol; 4-[(3S,4R)-4-(4-hydroxyphenyl)hexan-3-yl]phenol
• Synonyms: 4,4′-(1,2-Diethylethylene)diphenol; meso-3,4-Bis(4-hydroxyphenyl)hexane; Dihydrodiethylstilbestrol; Bibenzyl; Cycloestrol; Dihydro-stilbestro; Hexestrol; 4-[(1R,2S)-1-ethyl-2-(4-hydroxyphenyl)butyl]phenol; Hexestrol; 4,4′-(1,2-二乙基亚乙基)二苯酚; 二羟二苯己烷; 六羟春情素; 己烷雌酚

Database IDs

• CAS Number: 84-16-2
• EC Number: 201-518-1
• MDL Number: MFCD00068996
• Beilstein Number: 3209460
• PubChem SID: 99444402; 24870032; 24895805; 160968989
• PubChem CID: 192197

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.926587
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.3656373
• LogD (pH = 7.4): 5.36437
• Log P: 5.3656535
• Molar Refractivity: 82.6572 cm^3
• Polarizability: 32.048504 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.98
• LOG S: -4.29
• Solubility (Water): 1.39e-02 g/l

PROPERTIES

Safety Information

• Storage Condition: -20°C
• RTECS: SL0560850
• European Hazard Symbols: Toxic (T)
• German water hazard class: 2
• Risk Statements: 45
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H350
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Target: Estrogen receptor
• Gene Information: human ... ESR1(2099)rat ... Esr1(24890)

Product Information

• Purity: ≥98%
• Grade: analytical standard; VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H22O2

DETAILS

DrugBank - DB07931

Drug information: experimental

Selleck Chemicals - S2473

Research Area

• Description: Cancer

Biological Activity

• Description: Hexestrol binds to Erα and ERβ with EC50 of 0.07 nM and 0.175 nM, respectively.
• Targets: ERα; ERβ
• IC50: 0.07 nM (EC50); 0.175 nM (EC50) ^[1]
• In Vitro: Hexestrol binds to ERα with EC50 of 0.07 nM and to ERβ with EC50 of 0.175 nM. ^[1] Hexestrol inhibits activity of AKR1B13 with IC50 of 3.2 μM. ^[2] Hexestrol inhibits the d-galactose dehydrogenase activity of thermophilus aldose 1-dehydrogenase with IC50 of 0.063 mM. ^[3] Hexestrol inhibits the dehydrogenase activity of AKR1C20 towards 10 μM 4-androsten-3α-o1-17-one with IC50 values of 2.7 μM. ^[4] Hexestrol inhibits 17HSD5 with IC50 of 30 μM, and inhibits TBER1 with IC50 of 0.8 μM. ^[5] Hexestrol reacts with DNA through the catechol quinone, thus can be a carcinogen. ^[6]
• In Vivo: Hexestrol administered intraperitoneally at dose of 6 mg/kg may decrease ovulation in mice, as evident by smaller ovaries and decreased luteal bodies and oocytes. ^[7]
• Features: Much higher ERβ binding selectivity than Erα

Protocol

• Protocol: Kinase Assay ^[1]
• Estrogen Receptor Binding Affinity Assays: Relative binding affinities are determined by a competitive radiometric binding assay, using 10 nM [^3H]estradiol as tracer, and purified full-length human ERα and ERβ. Incubations are for 18–24 h at 0 °C, then the receptor-ligand complexes are absorbed onto hydroxyapatite and unbound ligand is washed away. The binding affinities are expressed as relative binding affinity (RBA) values, with the RBA of estradiol set to 100. The values given are the average ± range or SD of two or more independent determinations. Hexestrol is tested as racemate.
• Protocol: Animal Study ^[7]
• Animal Models: adult mice aged 90-120 days
• Formulation: Saline
• Doses: 3 mg/kg and 6 mg/kg
• Administration: administered intraperitoneally once daily for 30 days

References

• References: [1] Waibel M, et al. Eur J Med Chem, 2009, 44(9), 3412-3424.
• References: [2] Endo S, et al. Chem Biol Interact, 2009, 178(1-3), 151-157.
• References: [3] Asada Y, et al. Chem Biol Interact. 2009, 178(1-3), 117-126.
• References: [4] Matsumoto K, et al. Biol Pharm Bull, 2006, 29(3), 539-542.
• References: [5] Ishikura S, et al. J Biochem, 2006, 139(6), 1053-1063.
• References: [6] Ishikura S, et al. Ann N Y Acad Sci, 2004, 1028, 247-257.

Sigma Aldrich - 46320

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - H7753

Biochem/physiol Actions
The carcinogen hexestrol is a nonsteroidal synthetic estrogen. Metabolic activation of hexestrol to its quinone, which reacts with DNA to form analogous depurinating adducts, may be a primary critical event leading to oncogenic mutations and cancer initiation.
Linkage
己烯雌酚的还原类似物。

REFERENCES

• Waibel M, et al. Eur J Med Chem, 2009, 44(9), 3412-3424.
• Endo S, et al. Chem Biol Interact, 2009, 178(1-3), 151-157.
• Asada Y, et al. Chem Biol Interact. 2009, 178(1-3), 117-126.
• Matsumoto K, et al. Biol Pharm Bull, 2006, 29(3), 539-542.
• Ishikura S, et al. J Biochem, 2006, 139(6), 1053-1063.
• Ishikura S, et al. Ann N Y Acad Sci, 2004, 1028, 247-257.