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(10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

Base Information Edit
  • Chemical Name:(10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
  • CAS No.:797-63-7
  • Molecular Formula:C21H28O2
  • Molecular Weight:312.452
  • Hs Code.:2937290090
  • European Community (EC) Number:229-433-5
  • NSC Number:759653
  • Wikipedia:Norgestrel
  • Wikidata:Q27163551
  • NCI Thesaurus Code:C703
  • RXCUI:7518
  • ChEMBL ID:CHEMBL4571597
  • Mol file:797-63-7.mol
(10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

Synonyms:18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (17alpha)-(+-)-;DL Norgestrel;DL-Norgestrel;Neogest;Norgestrel;Ovrette;Postinor;Wy 3707;Wy-3707;Wy3707

Suppliers and Price of (10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • D-(-)-Norgestrel
  • 50mg
  • $ 45.00
  • TRC
  • D-(-)-Norgestrel
  • 1g
  • $ 140.00
  • Tocris
  • Levonorgestrel ≥98%(HPLC)
  • 50
  • $ 61.00
  • Sigma-Aldrich
  • Levonorgestrel Pharmaceutical Secondary Standard; Certified Reference Material
  • 500mg
  • $ 129.00
  • Sigma-Aldrich
  • Levonorgestrel for system suitability 2 European Pharmacopoeia (EP) Reference Standard
  • $ 190.00
  • Sigma-Aldrich
  • Levonorgestrel for system suitability 2 European Pharmacopoeia (EP) Reference Standard
  • y0001618
  • $ 190.00
  • Sigma-Aldrich
  • Levonorgestrel European Pharmacopoeia (EP) Reference Standard
  • l0551000
  • $ 190.00
  • Sigma-Aldrich
  • Levonorgestrel United States Pharmacopeia (USP) Reference Standard
  • 125mg
  • $ 366.00
  • Sigma-Aldrich
  • D(?)-Norgestrel analytical standard
  • 1g
  • $ 333.00
  • Sigma-Aldrich
  • D(?)-Norgestrel analytical standard
  • 100mg
  • $ 49.10
Total 105 raw suppliers
Chemical Property of (10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Edit
Chemical Property:
  • Appearance/Colour:white solid 
  • Vapor Pressure:2.32E-10mmHg at 25°C 
  • Melting Point:206 °C 
  • Refractive Index:1.571 
  • Boiling Point:459.1 °C at 760 mmHg 
  • PKA:13.09±0.40(Predicted) 
  • Flash Point:195.4 °C 
  • PSA:37.30000 
  • Density:1.13 g/cm3 
  • LogP:3.88260 
  • Storage Temp.:2-8°C 
  • Solubility.:Practically insoluble in water, sparingly soluble in methylene chloride, slightly soluble in ethanol (96 per cent). 
  • Water Solubility.:10mg/L(temperature not stated) 
  • XLogP3:3.3
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:2
  • Exact Mass:312.208930132
  • Heavy Atom Count:23
  • Complexity:609
Purity/Quality:

99% *data from raw suppliers

D-(-)-Norgestrel *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn 
  • Hazard Codes:Xn,T 
  • Statements: 20/21/22-40-60 
  • Safety Statements: 22-36 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
  • Isomeric SMILES:CC[C@]12CCC3[C@H]4CCC(=O)C=C4CCC3C1CC[C@]2(C#C)O
  • Recent ClinicalTrials:Adherence With Continuous-dose Oral Contraceptive: Evaluation of Self-Selection and Use
  • Description Levonorgestrel exhibits some androgenic activity but no glucocortic oid or antimineraloc orticoid action. Levonorgestrel can be administered orally, transdermally (combined with estradiol and formulated as a 7-day patch), and for prolonged, continuous use, via an intrauterine device (IUD). The oral bioavailability of levonorgestrel is approximately 95%. From a protein binding pers pective, 48% of an oral dose is bound to SHBG, and 50% is bound to albumin. Levonorgestrel under goes metabolic reduction of its ketone and is hydroxylated.
  • Uses An emergency contraceptive. Levonorgestrel is safe, tolerated and effective in emergency contraception in woman progestin D-(-)-Norgestrel is an emergency contraceptive. Levonorgestrel is safe, tolerated and effective in emergency contraception in woman. Norgestimate USP Related Compound A.
Technology Process of (10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

There total 37 articles about (10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With sulfuric acid; water; In tetrahydrofuran; at 65 - 68 ℃;
Guidance literature:
Multi-step reaction with 6 steps
1: 80 percent NaH, Et3N / 1,2-dimethoxy-ethane; paraffin / 1.) 3.5 h, reflux; 2.) 40 min
2: 1.) 2,4,6-trimethylphenol, pyridine; 2.) oxalic acid / 1.) methylcyclohexane, 13.5 h, 98 deg C, irradiation
3: 99 percent / LiAlH4 / diethyl ether
4: 62 percent / K, aniline, NH3 / tetrahydrofuran / 1 h
5: 76 percent / 2-butanone, aluminium isopropylate, mol. sieve / benzene
6: 0.16 g / LDA / tetrahydrofuran
With pyridine; lithium aluminium tetrahydride; molecular sieve; Mesitol; ammonia; oxalic acid; aluminum isopropoxide; sodium hydride; triethylamine; aniline; butanone; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; paraffin; benzene;
DOI:10.1002/hlca.19850680430
Guidance literature:
Multi-step reaction with 2 steps
1: NBS / acetone
2: (i) liq. NH3 (ii) /BRN= 4147360/, benzene, Et2O
With N-Bromosuccinimide; In acetone;
DOI:10.1002/hlca.19710540852
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