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17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether

CAS：72-33-3
MW:310.43000
MF：C21H26O2

Mestranol is an orally active estrogenic steroid. It was the estrogen used in many of the first oral contraceptives

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Realated Product Infomation

1. Names and Identifiers

1.1 Name: 17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether

1.2 Synonyms: (17a)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol; (17b)-17-ethynyl-3-methoxyestra-1,3,5(10)-trien-17-ol; (17α)-3-Methoxy-19-norpregna-1(10),2,4-trien-20-yn-17-ol; (17α)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol; (8R,9S,13S,14S,17R)-17-éthynyl-3-méthoxy-13-méthyl-7,8,9,11,12,13,14,15,16,17-décahydro-6H-cyclopenta[a]phénanthrén-17-ol; (8R,9S,13S,14S,17R)-17-Ethinyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol; 17a-Ethynyl-3-methoxy-1,3,5(10)-estratrien-17b-ol; 17a-Ethynylestradiol 3-Methyl Ether; 17alpha-19-Norpregna-1,3,5(10)-trien-20-yn; 17α-Ethynylestradiol 3-methyl ether; 19-Nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-; 19-nor-17α-pregna-1,3,5(10)-trien-20-yn-17-ol,3-methoxy-; 19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, (17alpha)-; 19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, (17α)-; 3,17-beta-Dihydroxy-17-alpha-ethynyl-1,3,5(10)-estratriene-3-methyl ether; 3,17-beta-dihydroxy-17-alpha-ethynyl-1,3,5(10)-estratriene-3-methylether; 3-Methoxy-19-nor-17α-pregna-1,3,5(10)-trien-20-yn-17-ol; 8027 C. B.; Devocin; d-MVE; EE3ME; EINECS 200-777-8; Estra-1(10),2,4-trien-17-ol, 17-ethynyl-3-methoxy-, (17Β)-; estra-1,3,5(10)-trien-17-ol, 17-ethynyl-3-methoxy-, (17b)-; Estra-1,3,5(10)-trien-17Β-ol, 17-ethynyl-3-methoxy-; MESTRANOL; MFCD00003689; Norquen; Ovastol; RS 1044; SC 4725; Δ-MVE;

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1.3 CAS No.: 72-33-3

1.4 CID: 6291

1.5 EINECS: 200-777-8

1.6 Molecular Formula: C21H26O2

1.7 Inchi: InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1

1.8 InChkey: IMSSROKUHAOUJS-MJCUULBUSA-N

1.9 Canonical Smiles: CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)OC

1.10 Isomers Smiles: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC

2. Properties

2.1 Appearance: crystalline solid

2.2 Chemical Properties: Crystalline Solid

2.3 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.4 pKa: 13.10±0.40(Predicted)

2.5 Water Solubility: In double-distilled water, 0.32 mg/L

2.6 Stability: The shelf life of Norinyl-1 tablets is 5 years.

2.7 StorageTemp: Sealed in dry,2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A terminal acetylenic compound that is (17alpha)-17-ethynylestra-1(10),2,4-triene substituted by a methoxy group at position 3 and a hydroxy group at position 17.

3.2 Description: Mestranol is the 3-methyl ether of ethinylestradiol. It was the estrogen used in many of the first oral contraceptives.Target: Estrogen Receptor/ERRMestranol is absorbed very rapidly from the digestive tract and maximum plasma levels are attained in 1-4 hours, the majority at 1-2 hours. Detectable levels of mestranol are present 24 hours postingestion in 58% of subjects after a 50 μg dose and in 79% after a 100 μg dose. At all dose levels, highest plasma mestranol levels and area under t

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3.3 Usage: Mestranol is an orally active estrogenic steroid. It was the estrogen used in many of the first oral contraceptives

4. Safety and Handling

4.1 Safety Profile: Confirmed carcinogenwith experimental. neoplastigenic,tumorigenic, and teratogenic data.Moderately toxic by subcutaneous route.Human reproductive effects by ingestion:changes in ovaries and fallopian tubes,ferthty effects. Experimental reproductiveeffects. Mutation data reported. An FDAproprietary drug. A steroid used in oralcontraceptives. When heated todecomposition it emits acrid smoke andirritating fumes. 17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl etherSupplier

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4.2 Report: NTP 10th Report on Carcinogens. IARC Cancer Review: Human Limited Evidence IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 ,1979,p. 257.(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) ; Animal Sufficient Evidence IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 ,1974,p. 87.(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. 257.(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) .

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4.3 Safety: Confirmed carcinogen with experimental neoplastigenic, tumorigenic, and teratogenic data. Moderately toxic by subcutaneous route. Human reproductive effects by ingestion: changes in ovaries and fallopian tubes, fertility effects. Experimental reproductive effects. Mutation data reported. An FDA proprietary drug. A steroid used in oral contraceptives. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information
Hazard Codes: Xn?
Risk Statements: 36/37/38-40-48-68?
R36/37/38: Irritating to eyes, respiratory system and skin.?
R40: Limited evidence of a carcinogenic effect.?
R48: Danger of serious damage to health by prolonged exposure.
R68: Possible risk of irreversible effects.
Safety Statements: 22-26-36/37/39-45-36/37?
S22: Do not breathe dust.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36/37: Wear suitable protective clothing and gloves.
WGK Germany: 3
RTECS: RC8960000
?

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4.4 Specification: Crystalline Solid
usageEng:Orally active estrogenic steroid. It was the estrogen used in many of the first oral contraceptives
Safety Statements:22-26-36/37/39-45-36/37
22:Do not breathe dust
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37:Wear suitable protective clothing and gloves

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4.5 Toxicity: Organic Compound; Ether; Drug; Metabolite; Synthetic Compound

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Carcinogenicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H351 Suspected of causing cancer
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

72-33-3Total: 3 Synthesis Route

57-63-6 333 Suppliers

74-88-4

72-33-3 90 Suppliers

1624-62-0 69 Suppliers

74-86-2 65 Suppliers

72-33-3 90 Suppliers

8. Precursor and Product

precursor:

74-86-2

1066-54-2

57-63-6

1624-62-0

product:

75812-41-8

60134-76-1

75803-39-3

26011-40-5

17550-03-7

10382-22-6

22415-44-7

57-63-6

1624-62-0

9. Computed Properties

Molecular Weight：310.43000g/mol
Molecular Formula：C₂₁H₂₆O₂
Compound Is Canonicalized：True
XLogP3-AA：310.193280068
Monoisotopic Mass：310.193280068
Complexity：519
Rotatable Bond Count：2
Hydrogen Bond Donor Count：1
Hydrogen Bond Acceptor Count：2
Topological Polar Surface Area：29.5
Heavy Atom Count：：23
Defined Atom Stereocenter Count：5
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADceB4MAAAAAAAAAAAAAAAAAAAAYAAAAAwYMAAAAAAAGDBAAAAGgAACAAAD0SAmAIyBoAABgDAGiBCAAgCCAAgIAAIiAAGCIgMJiKEMRqAcCAkwBEIqAeAwPAPoAABAAAQAADAAAYAACAAAYAADAAAAA==