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56-53-1 分子结构
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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和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

引用这个纪录

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

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名称和登记号

名称和登记号

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

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 9.129198  质子受体
质子供体 LogD (pH = 5.5) 5.1937814 
LogD (pH = 7.4) 5.185866  Log P 5.193883 
摩尔折射率 83.2406 cm3 极化性 32.122524 Å3
极化表面积 40.46 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P 4.62  LOG S -4.39 
溶解度 1.09e-02 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
0.012 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand 查看数据来源
DMF expand 查看数据来源
DMSO expand 查看数据来源
Ethanol expand 查看数据来源
Methanol expand 查看数据来源
methanol: soluble0.1 g/mL, clear, faintly yellow expand 查看数据来源
外观
White to Off-White Solid expand 查看数据来源
熔点
169-172 expand 查看数据来源
169-172 °C expand 查看数据来源
169-172°C expand 查看数据来源
170 - 172°C expand 查看数据来源
170-172 °C(lit.) expand 查看数据来源
疏水性(logP)
4.956 expand 查看数据来源
5.07 [HANSCH,C ET AL. (1995)] expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Amber Vial, -20°C Freezer, Under Inert Atmosphere expand 查看数据来源
Room Temperature (15-30°C) expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
RTECS编号
WJ5600000 expand 查看数据来源
欧盟危险性物质标志
环境危害性(Nature polluting) 环境危害性(Nature polluting) (N) expand 查看数据来源
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
联合国危险货物编号
2811 expand 查看数据来源
3077 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
联合国危险货物等级
6.1 expand 查看数据来源
9 expand 查看数据来源
联合国危险货物包装类别(PG)
3 expand 查看数据来源
III expand 查看数据来源
澳大利亚Hazchem
2X expand 查看数据来源
危险公开号
45-61-36/37/38-51/53 expand 查看数据来源
R:45-36/37/38 expand 查看数据来源
安全公开号
53-36/37/39-45-60-61 expand 查看数据来源
S:28-29-36/37/39-45-53 expand 查看数据来源
欧盟危险货物分类
T2 expand 查看数据来源
欧盟危险识别号(EUHIN)
6.1B expand 查看数据来源
美国ERG指导号
154 expand 查看数据来源
TSCA收录
false expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS08 expand 查看数据来源
GHS09 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H315-H319-H335-H350-H360-H410 expand 查看数据来源
GHS警示性声明
P201-P261-P273-P305 + P351 + P338-P308 + P313-P501 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves, type P2 (EN 143) respirator cartridges expand 查看数据来源
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 查看数据来源
RID/ADR
UN 3077 9/PG 3 expand 查看数据来源
相关基因信息
human ... ESR1(2099), ESR2(2100), ESRRG(2104)mouse ... Esr1(13982)rat ... Ar(24208), Esr1(24890) expand 查看数据来源
生物活性机理
Encourages cornification of superficial vaginal-cells expand 查看数据来源
In the preovulatory-phase: produces changes in the tubular-mucosa expand 查看数据来源
The responsible for vaginal acidity caused by deposition of glycogen in the vaginal epithelium expand 查看数据来源
纯度
≥99% (HPLC) expand 查看数据来源
≥99.0% (HPLC) expand 查看数据来源
95% expand 查看数据来源
97% expand 查看数据来源
级别
VETRANAL™, analytical standard expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
应用领域
Also a strong ichthyotoxin and coronary vasodilator expand 查看数据来源
Antineoplastic agent expand 查看数据来源
Non-steroidal estrogen expand 查看数据来源
Empirical Formula (Hill Notation)
C18H20O2 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02101560 external link
Crystalline
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 -  218944 external link
包装
5 g in glass bottle
Sigma Aldrich -  46207 external link
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC
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.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • : 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)
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