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56-53-1 molecular structure
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4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

ChemBase ID: 140
Molecular Formular: C18H20O2
Molecular Mass: 268.3502
Monoisotopic Mass: 268.14632988
SMILES and InChIs

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

Cite this record

CBID:140 http://www.chembase.cn/molecule-140.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
IUPAC Traditional name
diethylstilbestrol
stil
estrogen
4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
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'-(3-Hexene-3,4-diyl)diphenol
DEB
DES
Diethylstilbesterol
Diethylstilbestrol BP
Diethylstilboesterol
Dietilestilbestrol
Percutatrine oestrogenique iscovesco
Rcra waste number U089
trans-Diethylstilbesterol
trans-Diethylstilbestrol
trans-Diethylstilboesterol
Diethylstilbestrol
Stilbesterol, DES
(E)-3,4-Bis(4-hydroxyphenyl)-3-hexene
DIETHYLSTILBESTEROL
Diethylstilbestrol
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
diethylstilboestrol
Stilbestrol
4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
(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
CAS Number
56-53-1
6898-97-1
EC Number
200-278-5
MDL Number
MFCD00002373
Beilstein Number
2056095
PubChem SID
46507453
24893887
160963603
24869934
24853100
PubChem CID
448537

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.129198  H Acceptors
H Donor LogD (pH = 5.5) 5.1937814 
LogD (pH = 7.4) 5.185866  Log P 5.193883 
Molar Refractivity 83.2406 cm3 Polarizability 32.122524 Å3
Polar Surface Area 40.46 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 4.62  LOG S -4.39 
Solubility (Water) 1.09e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.012 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand Show data source
DMF expand Show data source
DMSO expand Show data source
Ethanol expand Show data source
Methanol expand Show data source
methanol: soluble0.1 g/mL, clear, faintly yellow expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
169-172 expand Show data source
169-172 °C expand Show data source
169-172°C expand Show data source
170 - 172°C expand Show data source
170-172 °C(lit.) expand Show data source
Hydrophobicity(logP)
4.956 expand Show data source
5.07 [HANSCH,C ET AL. (1995)] expand Show data source
Storage Condition
-20°C expand Show data source
Amber Vial, -20°C Freezer, Under Inert Atmosphere expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
WJ5600000 expand Show data source
European Hazard Symbols
Nature polluting Nature polluting (N) expand Show data source
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
3077 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
9 expand Show data source
Packing Group
3 expand Show data source
III expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
45-61-36/37/38-51/53 expand Show data source
R:45-36/37/38 expand Show data source
Safety Statements
53-36/37/39-45-60-61 expand Show data source
S:28-29-36/37/39-45-53 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H315-H319-H335-H350-H360-H410 expand Show data source
GHS Precautionary statements
P201-P261-P273-P305 + P351 + P338-P308 + P313-P501 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
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 expand Show data source
RID/ADR
UN 3077 9/PG 3 expand Show data source
Gene Information
human ... ESR1(2099), ESR2(2100), ESRRG(2104)mouse ... Esr1(13982)rat ... Ar(24208), Esr1(24890) expand Show data source
Mechanism of Action
Encourages cornification of superficial vaginal-cells expand Show data source
In the preovulatory-phase: produces changes in the tubular-mucosa expand Show data source
The responsible for vaginal acidity caused by deposition of glycogen in the vaginal epithelium expand Show data source
Purity
≥99% (HPLC) expand Show data source
≥99.0% (HPLC) expand Show data source
95% expand Show data source
97% expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Also a strong ichthyotoxin and coronary vasodilator expand Show data source
Antineoplastic agent expand Show data source
Non-steroidal estrogen expand Show data source
Empirical Formula (Hill Notation)
C18H20O2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00255 external link
Item Information
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 external link
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 external link
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 - 46207 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - 218944 external link
Packaging
5 g in glass bottle
Sigma Aldrich - 32500 external link
Other Notes
A probe for studying the Fo "proton channel" of rat liver mitochondria1
Toronto Research Chemicals - D445026 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  http://www.drugbank.ca/drugs/DB00255
  • • Kharasch, N. et al., J.A.C.S., 1943, 65, 11, (synth)
  • • Solmssen, U.V., Chem. Rev., 1945, 37, 481, (rev, uv)
  • • 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
  • • White, W. A. et. al.: J. Agric. Food Chem. 19(2)
  • • 388-390 (1971).
  • • : 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
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