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

• ChemBase编号: 140
• 分子式: C18H20O2
• 平均质量: 268.3502
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol; 4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
• IUPAC传统名: 4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol; diethylstilbestrol; estrogen; stil
• 商标名: 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
• 别名: (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; 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

登记号

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

理论计算性质

JChem

• Acid pKa: 9.129198
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 5.1937814
• LogD (pH = 7.4): 5.185866
• Log P: 5.193883
• 摩尔折射率: 83.2406 cm^3
• 极化性: 32.122524 Å^3
• 极化表面积: 40.46 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 4.62
• LOG S: -4.39
• 溶解度: 1.09e-02 g/l

分子性质

理化性质

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

安全信息

• 保存条件: -20°C; Amber Vial, -20°C Freezer, Under Inert Atmosphere; Room Temperature (15-30°C)
• 保存注意事项: IRRITANT
• RTECS编号: WJ5600000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 有毒(Toxic) (T)
• 联合国危险货物编号: 2811; 3077
• 德国WGK号: 3
• 联合国危险货物等级: 6.1; 9
• 联合国危险货物包装类别(PG): 3; III
• 澳大利亚Hazchem: 2X
• 危险公开号: 45-61-36/37/38-51/53; R:45-36/37/38
• 安全公开号: 53-36/37/39-45-60-61; S:28-29-36/37/39-45-53
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• TSCA收录: false
• GHS危险品标识: GHS07; GHS08; GHS09
• GHS警示词: Danger
• GHS危险声明: H315-H319-H335-H350-H360-H410
• GHS警示性声明: P201-P261-P273-P305 + P351 + P338-P308 + P313-P501
• 个人保护装置: 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

药理学性质

• 相关基因信息: human ... ESR1(2099), ESR2(2100), ESRRG(2104)mouse ... Esr1(13982)rat ... Ar(24208), Esr1(24890)
• 生物活性机理: 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

产品相关信息

• 纯度: ≥99% (HPLC); ≥99.0% (HPLC); 95%; 97%
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 应用领域: Also a strong ichthyotoxin and coronary vasodilator; Antineoplastic agent; Non-steroidal estrogen
• Empirical Formula (Hill Notation): C18H20O2

详细说明

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

包装
5 g in glass bottle

Sigma Aldrich - 46207

法律信息
VETRANAL 商标 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.

参考文献

• : 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).
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• Busetta, B., Acta Cryst. B, 1973, 29, 2456, (struct)
• Engel, L.L. et al., Biomed. Mass Spectrom., 1978, 5, 582, (ms)
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• Metzler, M., Crit. Rev. Biochem., 1981, 10, 171, (rev, metab)
• Leimner, J. et al., Chem. Ber., 1982, 115, 3697, (synth, deriv)
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• 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
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• 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)