4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

• ChemBase ID: 140
• Molecular Formular: C18H20O2
• Molecular Mass: 268.3502
• Monoisotopic Mass: 268.14632988
• SMILES: Oc1ccc(/C(=C(\CC)/c2ccc(O)cc2)/CC)cc1
• Canonical SMILES: CC/C(=C(\c1ccc(cc1)O)/CC)/c1ccc(cc1)O
• InChI: InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3
• InChIKey: RGLYKWWBQGJZGM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol; 4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
• IUPAC Traditional name: 4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol; diethylstilbestrol; estrogen; stil
• Brand Name: Acnestrol; Agostilben; Antigestil; Bio-des; Bufon; Climaterine; Comestrol; Comestrol estrobene; Cyren; Cyren A; Dawe's destrol; Desma; Destrol; Di-Estryl; DiBestrol 2 Premix; Diastyl; Dibestrol; Dicorvin; Distilbene; Domestrol; Dyestrol; Estilben; Estilbin MCO; Estril; Estrobene; Estrogenine; Estromenin; Estrosyn; Follidiene; Fonatol; Grafestrol; Gynopharm; Hi-Bestrol; Idroestril; Iscovesco; Makarol; Menostilbeen; Micrest; Microest; Milestrol; Neo-Oestranol I; New-Estranol 1; OeKolp; Oestrogenine; Oestrol vetag; Oestromenin; Oestromensil; Oestromensyl; Oestromienin; Oestromon; Pabestrol; Palestrol; Protectona; Rumestrol 1; Rumestrol 2; Sedestran; Serral; Sexocretin; Sibol; Sintestrol; Stibilium; Stil; Stil-Rol; Stilbestroform; Stilbestrol; Stilbestrone; Stilbetin; Stilboefral; Stilboestroform; Stilboestrol; Stilbofolin; Stilbofollin; Stilbol; Stilkap; Stilphostrol; Synestrin; Synthestrin; Synthoestrin; Synthofolin; Syntofolin; Tampovagan stilboestrol; Tylosterone; Vagestrol; neo-Oestranol 1; strobene
• Synonyms: 4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol; Diethylstilbestrol; diethylstilboestrol; Stilbestrol; Stilbesterol, DES; (E)-3,4-Bis(4-hydroxyphenyl)-3-hexene; DIETHYLSTILBESTEROL; DEB; DES; Diethylstilbesterol; Diethylstilbestrol BP; Diethylstilboesterol; Dietilestilbestrol; Percutatrine oestrogenique iscovesco; Rcra waste number U089; trans-Diethylstilbesterol; trans-Diethylstilbestrol; trans-Diethylstilboesterol; Diethylstilbestrol; 4,4'-(3-Hexene-3,4-diyl)diphenol; Diethylstilbestrol, mixture of cis and trans; 4,4'-[(1E)-1,2-Diethyl-1,2-ethenediyl]bisphenol; (E)-4,4'-(1,2-Diethyl-1,2-ethenediyl)bisphenol; (E)-Diethylstilbestrol; 4,4'-Dihydroxy-α,β-diethylstilbene; 4,4'-Dihydroxydiethylstilbene; Agostilben; Antigestil; Bertrol; Bio-des; Bufon; Comestrol; Cyren; Cyren A; trans-Diethyl Stilbestrol; (E)-3,4-双(4-羟苯基)3-亚己基; 乙芪酚; 己烯雌酚; 己烯雌酚，顺式和反式异构体混合物

Database IDs

• CAS Number: 6898-97-1; 56-53-1
• EC Number: 200-278-5
• MDL Number: MFCD00002373
• Beilstein Number: 2056095
• PubChem SID: 160963603; 24869934; 46507453; 24893887; 24853100
• PubChem CID: 448537

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.129198
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.1937814
• LogD (pH = 7.4): 5.185866
• Log P: 5.193883
• Molar Refractivity: 83.2406 cm^3
• Polarizability: 32.122524 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.62
• LOG S: -4.39
• Solubility (Water): 1.09e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.012 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMF; DMSO; Ethanol; Methanol; methanol: soluble0.1 g/mL, clear, faintly yellow
• Apperance: White to Off-White Solid
• Melting Point: 169-172; 169-172 °C; 169-172°C; 170 - 172°C; 170-172 °C(lit.)
• Hydrophobicity(logP): 4.956; 5.07 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: -20°C; Amber Vial, -20°C Freezer, Under Inert Atmosphere; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: WJ5600000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2811; 3077
• German water hazard class: 3
• Hazard Class: 6.1; 9
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 45-61-36/37/38-51/53; R:45-36/37/38
• Safety Statements: 53-36/37/39-45-60-61; S:28-29-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: false
• GHS Pictograms: GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H335-H350-H360-H410
• GHS Precautionary statements: P201-P261-P273-P305 + P351 + P338-P308 + P313-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves, type P2 (EN 143) respirator cartridges; 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
• RID/ADR: UN 3077 9/PG 3

Pharmacology Properties

• Gene Information: human ... ESR1(2099), ESR2(2100), ESRRG(2104)mouse ... Esr1(13982)rat ... Ar(24208), Esr1(24890)
• Mechanism of Action: Encourages cornification of superficial vaginal-cells; In the preovulatory-phase: produces changes in the tubular-mucosa; The responsible for vaginal acidity caused by deposition of glycogen in the vaginal epithelium

Product Information

• Purity: ≥99% (HPLC); ≥99.0% (HPLC); 95%; 97%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Also a strong ichthyotoxin and coronary vasodilator; Antineoplastic agent; Non-steroidal estrogen
• Empirical Formula (Hill Notation): C18H20O2

DETAILS

MP Biomedicals - 02101560

Crystalline

DrugBank - DB00255

• Drug Groups: approved
• Description: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed)
• Indication: Used in the treatment of prostate cancer. Previously used in the prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery.
• Pharmacology: Diethylstilbestrol is a synthetic estrogen that was developed to supplement a woman's natural estrogen production. In 1971, the Food and Drug Administration (FDA) issued a Drug Bulletin advising physicians to stop prescribing DES to pregnant women because it was linked to a rare vaginal cancer in female offspring.
• Toxicity: Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• References: : Leuprolide versus diethylstilbestrol for metastatic prostate cancer. The Leuprolide Study Group. N Engl J Med. 1984 Nov 15;311(20):1281-6. [Pubmed] ; DIECKMANN WJ, DAVIS ME, RYNKIEWICZ LM, POTTINGER RE: Does the administration of diethylstilbestrol during pregnancy have therapeutic value? Am J Obstet Gynecol. 1953 Nov;66(5):1062-81. [Pubmed] ; Ingle JN, Ahmann DL, Green SJ, Edmonson JH, Bisel HF, Kvols LK, Nichols WC, Creagan ET, Hahn RG, Rubin J, Frytak S: Randomized clinical trial of diethylstilbestrol versus tamoxifen in postmenopausal women with advanced breast cancer. N Engl J Med. 1981 Jan 1;304(1):16-21. [Pubmed] ; Kuchera LK: Postcoital contraception with diethylstilbestrol. JAMA. 1971 Oct 25;218(4):562-3. [Pubmed] ; Herbst AL, Ulfelder H, Poskanzer DC: Adenocarcinoma of the vagina. Association of maternal stilbestrol therapy with tumor appearance in young women. N Engl J Med. 1971 Apr 15;284(15):878-81. [Pubmed]
• External Links: Wikipedia

Selleck Chemicals - S1859

Research Area: Endocrinology
Biological Activity:
Diethylstilbestrol(Stilbestrol), a synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. [1]

Sigma Aldrich - D4628

Biochem/physiol Actions
Diethylstilbestrol is a synthetic estrogen with carcinogenic properties. Causes renal clear-cell carcinoma in Syrian hamster. In humans it causes increased risk of breast cancer, clear cell adenocarcinoma (CCA) of the vagina and cervix, and reproductive anomalies. Used in the treatment of prostate cancer to block the production of testosterone.

Sigma Aldrich - 218944

Packaging
5 g in glass bottle

Sigma Aldrich - 46207

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

Sigma Aldrich - 32500

Other Notes
A probe for studying the Fo "proton channel" of rat liver mitochondria1

Toronto Research Chemicals - D445026

A synthetic, nonsteroidal estrogen.Recomended solvents are DMSO, DMF and ethanol, even in these solvents do not store in solution for any prolonged period of time.

REFERENCES

• : Leuprolide versus diethylstilbestrol for metastatic prostate cancer. The Leuprolide Study Group. N Engl J Med. 1984 Nov 15;311(20):1281-6. Pubmed
• DIECKMANN WJ, DAVIS ME, RYNKIEWICZ LM, POTTINGER RE: Does the administration of diethylstilbestrol during pregnancy have therapeutic value? Am J Obstet Gynecol. 1953 Nov;66(5):1062-81. Pubmed
• Ingle JN, Ahmann DL, Green SJ, Edmonson JH, Bisel HF, Kvols LK, Nichols WC, Creagan ET, Hahn RG, Rubin J, Frytak S: Randomized clinical trial of diethylstilbestrol versus tamoxifen in postmenopausal women with advanced breast cancer. N Engl J Med. 1981 Jan 1;304(1):16-21. Pubmed
• Kuchera LK: Postcoital contraception with diethylstilbestrol. JAMA. 1971 Oct 25;218(4):562-3. Pubmed
• Herbst AL, Ulfelder H, Poskanzer DC: Adenocarcinoma of the vagina. Association of maternal stilbestrol therapy with tumor appearance in young women. N Engl J Med. 1971 Apr 15;284(15):878-81. Pubmed
• http://www.drugbank.ca/drugs/DB00255
• White, W. A. et. al.: J. Agric. Food Chem. 19(2)
• 388-390 (1971).
• Doskosch, J. et al., Monatsh. Chem., 1953, 84, 1146, (isom)
• Busetta, B., Acta Cryst. B, 1973, 29, 2456, (struct)
• Engel, L.L. et al., Biomed. Mass Spectrom., 1978, 5, 582, (ms)
• Crawley, G.C., Kirk-Othmer Encycl. Chem. Technol., 3rd edn., Wiley, 1978, 12, 658, (pharmacol, toxicol)
• IARC Monog., 1979, 21, 131; 173; Suppl. 6, 250; Suppl. 7, 273, (rev, tox)
• Williard, P.G. et al., Tet. Lett., 1980, 21, 3731, (synth)
• Metzler, M., Crit. Rev. Biochem., 1981, 10, 171, (rev, metab)
• Leimner, J. et al., Chem. Ber., 1982, 115, 3697, (synth, deriv)
• Schneider, M. et al., Eur. J. Med. Chem. (Chim. Ther.), 1982, 17, 49, (synth, deriv)
• Inamori, Y. et al., Chem. Pharm. Bull., 1985, 33, 4478, (pharmacol, uv, ir, pmr)
• Duax, W.L. et al., Environ. Health Perspect., 1985, 61, 111, (cryst struct)
• Edelman, D.A., DES/Diethylstilbestrol - New Perspectives, MTP Press, 1986, (book)
• Darden, T. et al., J.A.C.S., 1986, 108, 207, (conformn)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4805; 4885; 5765
• Oda, T. et al., Chem. Pharm. Bull., 1988, 36, 1534, (cmr)
• Al-Badr, A.A. et al., Anal. Profiles Drug Subst., 1990, 19, 145, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1185; 1195
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DKA200; DKA600; DKB000; TEE300
• Kharasch, N. et al., J.A.C.S., 1943, 65, 11, (synth)
• Solmssen, U.V., Chem. Rev., 1945, 37, 481, (rev, uv)