ChemicalBook > CAS DataBase List > Quinestrol

Quinestrol

Product Name
Quinestrol
CAS No.
152-43-2
Chemical Name
Quinestrol
Synonyms
eston;eecpe;w3566;EE2CPE;qui-lea;estrovis;plestrovis;QUINESTROL;estrovister;estrovis4000
CBNumber
CB6189992
Molecular Formula
C25H32O2
Formula Weight
364.52
MOL File
152-43-2.mol
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Quinestrol Property

Melting point:
107-108°
alpha 
D25 +5° (c = 0.5 in dioxane)
Boiling point:
435.69°C (rough estimate)
Density 
1.0693 (rough estimate)
refractive index 
1.4480 (estimate)
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)
pka
13.10±0.40(Predicted)
form 
Solid
color 
White to Off-White
Merck 
14,8055
CAS DataBase Reference
152-43-2(CAS DataBase Reference)
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Safety

Hazard Codes 
T
Risk Statements 
45-61-20/21/22-46
Safety Statements 
53-22-36/37/39-45
WGK Germany 
3
RTECS 
RC8948000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H350May cause cancer

H360May damage fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
E7887
Product name
17α-Ethynylestradiol 3-cyclopentyl ether
Packaging
100mg
Price
$52.9
Updated
2025/07/31
Sigma-Aldrich
Product number
PH001408
Product name
3-(CYCLOPENTYLOXY)-17-ETHYNYLESTRA-1(10),2,4-TRIEN-17-OL
Purity
AldrichCPR
Packaging
1MG
Price
$81.6
Updated
2023/06/20
Cayman Chemical
Product number
10006320
Product name
Quinestrol
Purity
≥98%
Packaging
100mg
Price
$36
Updated
2024/03/01
Cayman Chemical
Product number
10006320
Product name
Quinestrol
Purity
≥98%
Packaging
250mg
Price
$84
Updated
2024/03/01
Cayman Chemical
Product number
10006320
Product name
Quinestrol
Purity
≥98%
Packaging
500mg
Price
$155
Updated
2024/03/01
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Quinestrol Chemical Properties,Usage,Production

Description

Quinestrol is a synthetic estrogen that is effective in hormone replacement therapy. It is a 3-cyclopentyl ether of ethynyl estradiol. After gastrointestinal absorption, it is stored in adipose tissue, where it is slowly released and metabolized in the liver to its active form, ethinyl estradiol. Quinestrol has found limited use in suppressing lactation in postpartum women and, in combination with synthetic progestogens, as contraceptive therapy, although additional studies are needed for both applications.

Uses

antibacterial, antimycoplasmal, isoleucyl-tRNA synthetase inhibitor

Uses

Quinestrol is an estrogen-like compound.

Definition

ChEBI: Quinestrol is a 17-hydroxy steroid and a terminal acetylenic compound. It has a role as a xenoestrogen. It is functionally related to a 17beta-estradiol.

brand name

Estrovis (Parke-Davis).

Synthesis

1852-81-9

1066-54-2

152-43-2

The general procedure for the synthesis of (8R,9S,13S,14S,17R)-3-(cyclopentyloxy)-17-ethynyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol using nilestrol impurity 1 and trimethylsilylacetylene was carried out as follows: firstly, a mixture of 1x and 1x was prepared according to literature methods from 19-hydroxy androst-4-ene-3,17-dione to prepare a mixture of 1 and 1x in 80% overall yield. A solution of the 1-mixture (2.04 g, 6.0 mmol), tricyclopentyl orthoformate (8.04 g, 30 mmol) and TfOH (552 μL, 6.0 mmol) in cyclopentanol (60 mL) was stirred for 2 h at 100 °C under inert atmosphere. After completion of the reaction, the reaction was quenched with saturated NaHCO3 solution. The organic solvent was removed under reduced pressure and the residue was diluted with ethyl acetate and washed with brine. The organic phase was dried over Na2SO4, concentrated under reduced pressure and separated by silica gel column chromatography to give the 2b-mixture as a white solid (1.63 g). Next, Raney Ni (1.6 g) was washed several times with dry THF under inert atmosphere. A solution of anhydrous THF (180 mL) of the 2b-mixture (1.63 g) was added to Raney Ni. The suspension was stirred at room temperature and the progress of the reaction was monitored by HPLC. After completion of the reaction (1.5 h), the suspension was filtered. The filtrate was concentrated and separated by silica gel column chromatography to afford estrone 3-cyclopentyl ether (2b) as a white solid (1.62 g, 79% overall yield). Subsequently, n-BuLi (1.2 mL, 3.0 mmol, 2.5 N) was added to a THF (2 mL) solution of ethynyltrimethylsilane (424 μL, 3.0 mmol) under an inert atmosphere at -20 °C. After 0.5 h, a THF (4 mL) solution of ketone 2b (338 mg, 1.0 mmol) was added to a lithium acetate solution at -20 °C After 1 h, methanol (6 mL) and KOH (224 mg, 4 mmol) were added to the mixture and stirred at room temperature for 0.5 h. The reaction was subsequently quenched with 2N hydrochloric acid. The organic solvent was removed under reduced pressure and the residue was diluted with ethyl acetate and washed with saturated NaHCO3 and brine. The organic phase was dried over Na2SO4, concentrated under reduced pressure and separated by silica gel column chromatography to give the target product as a white solid (340 mg, 93%). The melting point of the product was 94-96 °C; [α]D23.4 = +11.3 (c 1, CHCl3); 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J=8.6 Hz, 1H), 6.68 (dd, J=8.5,2.3 Hz, 1H), 6.61 (d, J=2.7 Hz, 1H), 4.74-4.70 ( m, 1H), 2.91-2.79 (m, 2H), 2.61 (s, 1H), 0.89 (s, 3H); 13C NMR (101MHz, CDCl3) δ155.9,137.8,132.0,126.2,115.5,112.9,87.5,79.9,79.0,74.0,49.4,47.1 ,43.5,39.4,38.9,32.9,32.7,29.8,27.3,26.3,24.0,22.8,12.7; HRMS (ESI) calculated value of C25H33O2[M+H]+: 365.2402, measured value 365.2472.

References

[1]. baumgardner sb, condrea h, daane ta, et al. replacement estrogen therapy for menopausal vasomotor flushes. comparison of quinestrol and conjugated estrogens. obstet gynecol. 1978 apr;51(4):445-52.
[2]. skouby, s.o. criteria for the selection of an optimal estrogen replacement. gynecological endocrinology 15, 60-67 (2001).
[3]. li j, chen f, li c,et al. quinestrol induces spermatogenic apoptosis in vivo via increasing pro-apoptotic proteins in adult male mice. tissue cell. 2014 oct;46(5):318-25.
[4]. li j, chen f, chen y, et al. mitochondrial- and fas-l-mediated pathways involved in quinestrol induced spermatogenic apoptosis in adult rat testes. toxicol mech methods. 2014 dec;24(9):609-15.

Quinestrol Preparation Products And Raw materials

Raw materials

Tetrahydrofuran Bromocyclopentane

Preparation Products

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Quinestrol Suppliers

China 124 Europe 2 Germany 1 India 2 Japan 1 South Korea 1 Switzerland 2 United Kingdom 4 United States 21 Global 158
LGM Pharma
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888-539-0666
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Musechem
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+1-800-259-7612
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+1-800-259-7612
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TargetMol Chemicals Inc.
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+1-781-999-5354; +17819995354
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marketing@targetmol.com
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InvivoChem
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+1-708-310-1919 +1-13798911105
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sales@invivochem.cn
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TargetMol Chemicals Inc.
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marketing@targetmol.com
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TargetMol Chemicals Inc.
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View Lastest Price from Quinestrol manufacturers

Shaanxi TNJONE Pharmaceutical Co., Ltd
Product
Quinestrol 152-43-2
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20tons
Release date
2024-04-25
Shaanxi Dideu Medichem Co. Ltd
Product
Quinestrol 152-43-2
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
1000KG
Release date
2024-07-16
Hangzhou ICH Biofarm Co., Ltd
Product
Quinestrol 152-43-2
Price
US $0.00-0.00/g
Min. Order
1g
Purity
98.0%
Supply Ability
100kg
Release date
2023-06-29

152-43-2, QuinestrolRelated Search:

PENTYL ETHER Difenoconazole Ethylbenzene Dimethyl ether 2-Butoxyethanol Ethynyl estradiol 5-METHYL-1-HEXYN-3-OL ISONONYLPHENOL-ETHOXYLATE (S)-1-OCTYN-3-OL 17-alpha-methyloestradiol-17-beta 3-CYCLOHEXYL-1-PROPYNE 1-Ethoxy-4-(trans-4-propylcyclohexyl)benzene 3,6-DIMETHYL-1-HEPTYN-3-OL CYCLOPENTYLACETYLENE Nilestriol 4-METHYL-1-PENTYN-3-OL 3-Methylether-estradiol Diethyl ether

  • 17-alpha-ethinylestradiol3-cyclopentylether
  • 3-(cyclopentyloxy)-(17-alpha)-19-norpregna-5(10)-trien-20-yn-17-ol
  • 3-(cyclopentyloxy)-19-nor-17-alpha-pregna-1,3,5(10)-trien-20-yn-17-ol
  • 5(10)-trien-20-yn-17-ol,3-(cyclopentyloxy)-19-nor-17-alpha-pregna-3
  • eecpe
  • eston
  • 17ALPHA-ETHYLNYL-1,3,5[10]ESTRATRIENE-3,17BETA-DIOL 3-CYCLOPENTYL ETHER
  • 17a-ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-cyclopentyl ether
  • 17a-ethynylestradiol 3-cyclopentyl ether
  • (17ALPHA-3-(CYCLOPENTYLOXY)-19-NORPREGNA-1,3,5(10)TRIENE-20-YN-17-OL
  • 17α-Ethynylestradiol 3-cyclopentyl ether
  • Quinestrol, 17α-Ethynyl-1,3,5(10)-estratriene-3,17β-diol 3-cyclopentyl ether
  • 17a-Ethynylestradiol 3-cyclopentyl ether17a-ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-cyclopentyl ether
  • 19-Nor-17a-pregna-1,3,5(10)-trien-20-yn-17-ol, 3-(cyclopentyloxy)-
  • 3-(Cyclopentyloxy)-19-nor-17a-pregna-1,3,5(10)-trien-20-yn-17-ol<br />
  • 3-Cyclopentyloxy-17a-ethynyl-1,3,5(10)-estratrien-17-ol
  • Ethynylestradiol-3-cyclopentyl ether
  • (17R)-3-(Cyclopentyloxy)-19-norpregna-1,3,5(10)-trien-20-yn-17-ol
  • (8R,9S,13S,14S,17R)-3-(cyclopentoxy)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
  • (8R,9S,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
  • 17ALPHA-ETHYNYL-1,3,5(10)-ESTRATRIENE-3,17BETA-DIOL 3-CYCLOPENTYL ETHER
  • 3-cyclopentyloxy-17-alpha-ethynyloestra-1,3,5(10)-trien-17-beta-ol
  • 17α-Ethynyl-1,3,5(10)-estratriene-3,17β-diol 3-cyclopentyl ether
  • EE2CPE
  • Ethinylestradiol 3-cyclopentyl ether
  • 8-cyclopentyloxy-1-ethynyl-12a-methyl-2,3,4,4a,4b,5,6,10b,11,12-decahydrochrysen-1-ol
  • estradiol-17-beta3-cyclopentylether
  • estrovis
  • estrovis4000
  • estrovister
  • plestrovis
  • qui-lea
  • w3566
  • QUINESTROL
  • 17ALPHA-ETHYNYLESTRADIOL-3-CYCLOPENTYL ETHER
  • Quinestrol &gt
  • Quinestrol Quinestrol
  • 19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-(cyclopentyloxy)-, (17α)-
  • QUINESTROL 152-43-2
  • Quinestrol (W-3566)
  • (8R,9S,13S,14S,17R)-3-(Cyclopentyloxy)-17-ethynyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol
  • Quinestrol, 10 mM in DMSO
  • 152-43-2
  • C25H32O2
  • BACTROBAN