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797-63-7

Basic Information
CAS No.: 797-63-7
Name: Levonorgestrel
Article Data: 27
Cas Database
Molecular Structure:
Molecular Structure of 797-63-7 (Levonorgestrel)
Formula: C21H28O2
Molecular Weight: 312.452
Synonyms: 18,19-Dinor-17a-pregn-4-en-20-yn-3-one,13-ethyl-17-hydroxy- (7CI,8CI);(-)-Norgestrel;13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one;13-Ethyl-17a-ethynyl-17-hydroxygon-4-en-3-one;17a-Ethynyl-13-ethyl-19-nortestosterone;17a-Ethynyl-13b-ethyl-3-oxo-4-estren-17b-ol;17a-Ethynyl-18-homo-19-nortestosterone;18-Methylnorethindrone;19-Nortestosterone, 17-ethynyl-18-methyl-;D-(-)-Norgestrel;Dexnorgestrel;Femilis;Femilis Slim;Follistrel;Jadelle;Lng-IUS;Microlut;Microval;Mirena;Norgestrelem;Norlevo;Norplant;Norplant 2;Postinor 2;Wy 5104;d-(17a)-17-Hydroxy-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one;18,19-Dinorpregn-4-en-20-yn-3-one,13-ethyl-17-hydroxy-, (17a)-;
EINECS: 212-349-8
Density: 1.13 g/cm3
Melting Point: 206 °C
Boiling Point: 459.1 °C at 760 mmHg
Flash Point: 195.4 °C
Solubility: N/A
Appearance: white solid
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-40
Safety: 22-36
Transport Information: N/A
PSA: 37.30000
LogP: 3.88260
Synthetic route
14507-51-8

13β-ethyl-3-methoxy-17α-ethynyl-gona-2,5(10)-dien-17β-ol

Conditions
ConditionsYield
With sulfuric acid; water In tetrahydrofuran at 65 - 68℃;84.6%
With hydrogenchloride; water In methanol at 55 - 60℃; for 3h;84.6%
With hydrogenchloride In methanol; water; ethyl acetate; benzene
With sulfuric acid In tetrahydrofuran at 65 - 68℃; Product distribution / selectivity;
With hydrogenchloride In methanol; water; ethyl acetate; benzene

acetylene

acetylene

Conditions
ConditionsYield
(i) Li, H2NCH2CH2NH2, THF, (ii) aq. HCl, MeOH; Multistep reaction;
With hydrogenchloride; lithium diisopropyl amide 1.) THF, 2.5 h; 2.) MeOH, 60-70 deg C, 3 h; Yield given. Multistep reaction;
With hydrogenchloride; lithium 1.) ethylenediamine, 1 h; 2.) THF, r.t., 2 h; 3.) MeOH, 45-50 degC, 45 min; Yield given. Multistep reaction;

lithium acetylide

lithium acetylide

797-63-7

levonorgestrel

Conditions
ConditionsYield
With hydrogenchloride; cerium(III) chloride 1) THF, room temperature, 1 h, 2) MeOH, 0 deg C, 0.5 h; Yield given. Multistep reaction;
139590-87-7

3-methoxy-13β-ethyl-gona-3,5-dien-17-one

4301-14-8

acetylenemagnesium bromide

797-63-7

levonorgestrel

Conditions
ConditionsYield
With hydrogenchloride; cerium(III) chloride 1) THF, room temperature, 1 h, 2) MeOH, 0 deg C, 0.5 h; Yield given. Multistep reaction;
14507-49-4

D-13β-ethyl-17β-hydroxy-3-methoxy-gona-2,5(10)-diene

797-63-7

levonorgestrel

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 percent / mol. sieve, 2-butanone, aluminium isopropylate / benzene / 12 h / Heating
2: 1.) LDA; 2.) 6 percent HCl / 1.) THF, 2.5 h; 2.) MeOH, 60-70 deg C, 3 h
View Scheme
Multi-step reaction with 2 steps
1: Al(OiPr)3 / butan-2-one; benzene / Heating
2: (i) Li, H2NCH2CH2NH2, THF, (ii) aq. HCl, MeOH
View Scheme
Multi-step reaction with 3 steps
1: water; cyclohexanone; toluene
2: tetrahydrofuran; water
3: hydrogenchloride / methanol; water; ethyl acetate; benzene
View Scheme
Multi-step reaction with 3 steps
2: tetrahydrofuran; water
3: hydrogenchloride / methanol; water; ethyl acetate; benzene
View Scheme
75863-25-1

2-Trimethylsilyl-1-(4-methoxy-2-methylphenyl)-2-propen-1-on

797-63-7

levonorgestrel

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) 80 percent NaH; 2.) 10 percent H2SO4 / 1.) DME, parrafin oil, 3.5 h, reflux; Et2O, -20 deg C, 30 min; 2.) MeOH, 24 h
3: 84 percent / mol. sieve, 2-butanone, aluminium isopropylate / benzene / 12 h / Heating
4: 1.) LDA; 2.) 6 percent HCl / 1.) THF, 2.5 h; 2.) MeOH, 60-70 deg C, 3 h
View Scheme

(2R)-2-ethyl-3-vinyl-1-cyclopentanon

797-63-7

levonorgestrel

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) 80 percent NaH; 2.) 10 percent H2SO4 / 1.) DME, parrafin oil, 3.5 h, reflux; Et2O, -20 deg C, 30 min; 2.) MeOH, 24 h
3: 84 percent / mol. sieve, 2-butanone, aluminium isopropylate / benzene / 12 h / Heating
4: 1.) LDA; 2.) 6 percent HCl / 1.) THF, 2.5 h; 2.) MeOH, 60-70 deg C, 3 h
View Scheme
101025-85-8

13-Ethyl-3-methoxy-6,7:8,9-disecogona-1,3,5(10),7-tetraen-9,17-dion

797-63-7

levonorgestrel

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: 84 percent / mol. sieve, 2-butanone, aluminium isopropylate / benzene / 12 h / Heating
3: 1.) LDA; 2.) 6 percent HCl / 1.) THF, 2.5 h; 2.) MeOH, 60-70 deg C, 3 h
View Scheme
2911-81-1, 5941-86-6, 85760-97-0

13β-Aethyl-3-methoxy-gonapentaen-(1.3.5(10).8.14)-ol-(17β)-acetat

797-63-7

levonorgestrel

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: H2 / Pd-CaCO3 / benzene; tetrahydrofuran
2: KOH / methanol
3: (i) LiNH2, liq. NH3, PhNH2, THF, (ii) AcOH, EtOH
4: Al(OiPr)3 / butan-2-one; benzene / Heating
5: (i) Li, H2NCH2CH2NH2, THF, (ii) aq. HCl, MeOH
View Scheme
7443-72-3

18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol

797-63-7

levonorgestrel

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) LiNH2, liq. NH3, PhNH2, THF, (ii) AcOH, EtOH
2: Al(OiPr)3 / butan-2-one; benzene / Heating
3: (i) Li, H2NCH2CH2NH2, THF, (ii) aq. HCl, MeOH
View Scheme
Multi-step reaction with 5 steps
1: ammonium chloride; ammonia / tetrahydrofuran; water; aniline
2: ammonia; lithium / tetrahydrofuran; ethanol; water
4: tetrahydrofuran; water
5: hydrogenchloride / methanol; water; ethyl acetate; benzene
View Scheme
Multi-step reaction with 5 steps
1: ammonium chloride; ammonia / tetrahydrofuran; water; aniline
2: ammonia; lithium / tetrahydrofuran; ethanol; water
3: water; cyclohexanone; toluene
4: tetrahydrofuran; water
5: hydrogenchloride / methanol; water; ethyl acetate; benzene
View Scheme
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Consensus Reports

IARC Cancer Review: Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 ,1974,p. 201.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 ,1979,p. 479.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 ,1979,p. 479.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210)

Specification

The Levonorgestrel, with the CAS registry number 797-63-7,is also known as D(-)-13beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one. It belongs to the product categories of Pharmaceuticals;Steroid and Hormone. This chemical's molecular formula is C21H28O2 and molecular weight is 312.45.Its EINECS number is 212-349-8. What's more,Its systematic name is Levonorgestrel. It is a White Solid which is an emergency contraceptive. Levonorgestrel is safe, tolerated and effective in emergency contraception in woman.It is a synthetic progestational hormone with actions similar to those of  and Progesterone about twice as potent as its racemic or (+-)-isomer (NORGESTREL). It is used for contraception, control of menstrual disorders, and treatment of endometriosis.

Physical properties about Levonorgestrel are:
(1)ACD/LogP: 3.92; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.92; (4)ACD/LogD (pH 7.4): 3.92; (5)ACD/BCF (pH 5.5): 557.22; (6)ACD/BCF (pH 7.4): 557.22; (7)ACD/KOC (pH 5.5): 3215.19; (8)ACD/KOC (pH 7.4): 3215.18; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.571; (13)Molar Refractivity: 90.18 cm3; (14)Molar Volume: 274.3 cm3; (15)Polarizability: 35.75×10-24 cm3; (16)Surface Tension: 48.3 dyne/cm; (17)Enthalpy of Vaporization: 82.99 kJ/mol; (18)Vapour Pressure: 2.32E-10 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 8; (21)Exact Mass: 312.20893; (22)MonoIsotopic Mass: 312.20893; (23)Topological Polar Surface Area: 37.3; (24)Heavy Atom Count: 23; (25)Complexity: 609.

People can use the following data to convert to the molecule structure:
(1)SMILES:O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)CC)CC4
(2) InChI:InChI=1/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1 
(3)InChIKey:WWYNJERNGUHSAO-XUDSTZEEBP

Safety information of Levonorgestrel:
When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also has limited evidence of a carcinogenic effect. So people should not breathe dust. If you want to contact this product, you must wear suitable protective clothing.

Uses of Levonorgestrel:
Levonorgestrel is used in monophasic and triphasic formulations of combined oral contraceptive pills at low doses. It is also used in emergency contraceptive pills (ECPs), both in a combined Yuzpe regimen which includes estrogen, and as a levonorgestrel-only method. This drug has many side effects, including nausea, vomiting, stomach pain, dizziness, breast tenderness, tiredness and weakness, headache, menstrual changes, and diarrhea. It is also a pregnancy hormone drug.