Description

Mestranol (CAS: 72-33-3), also known as Ethynylestradiol 3-methyl ether, is a synthetic estrogen with the molecular formula C₂₁H₂₆O₂. This compound is widely utilized in pharmaceutical research and development, particularly in hormonal therapies. Mestranol is a derivative of ethinyl estradiol and exhibits potent estrogenic activity, making it a key component in oral contraceptives and hormone replacement therapies. Its high purity and stability ensure reliable performance in laboratory and clinical applications. Available in various formulations, this product is ideal for researchers and scientists focusing on endocrinology, reproductive health, and steroid chemistry.

Properties

• CAS Number: 72-33-3
• Complexity: 519
• IUPAC Name: (8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
• 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
• InChI Key: IMSSROKUHAOUJS-MJCUULBUSA-N
• LogP: log Kow = 4.61
• Exact Mass: 310.193280068
• Molecular Formula: C21H26O2
• Molecular Weight: 310.4
• SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC
• Topological: 29.5
• Monoisotopic Mass: 310.193280068
• Physical Description: Solid
• Color/Form: Crystals from methanol or acetone
• Solubility: In double-distilled water, 0.32 mg/L
• Vapor Pressure: 9.75×10-9
• Stability/Shelf Life: The shelf life of Norinyl-1 tablets is 5 years.
• Synonyms: mestranol, 72-33-3, EE3ME, Mestranolum, Ethynylestradiol 3-methyl ether, 3-Methoxy-17alpha-ethynylestradiol, EE3-ME, 17-Ethynylestradiol 3-methyl ether, EEI3ME, EE-3ME, B2V233XGE7, CHEBI:6784, DTXSID0020814, MESTRANOL [INN], MESTRANOL [JAN], MESTRANOL [MI], MESTRANOL [HSDB], MESTRANOL [USAN], MESTRANOL [VANDF], NSC-84032, (8R,9S,13S,14S,17R)-17-Ethynyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol, EE3 ME, MESTRANOL [MART.], 3-Methoxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, MESTRANOL [USP-RS], MESTRANOL [WHO-DD], 19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, (17alpha)-, DTXCID20814, MESTRANOL [ORANGE BOOK], (8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol, MESTRANOL [EP MONOGRAPH], ENOVID COMPONENT MESTRANOL, OVULEN COMPONENT MESTRANOL, MESTRANOL [USP MONOGRAPH], 17-ethynyl-3-methoxyestra-1(10),2,4-trien-17beta-ol, 17-ethynyl-3-methoxyoestra-1(10),2,4-trien-17beta-ol, 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17beta-ol, (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-estratriene, MESTRANOL (MART.), 19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, (17.alpha.)-, MESTRANOL (USP-RS), MESTRANOL (EP MONOGRAPH), MESTRANOL (USP MONOGRAPH), (17beta)-17-ethynyl-3-methoxyestra-1(10),2,4-trien-17-ol, (17alpha)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol, (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-oestratriene, 3-METHOXY-19-NOR-17.ALPHA.-PREGNA-1,3,5(10)-TRIEN-20-YN-17-OL., (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol, Ethinyl Estradiol 3 Methyl Ether, Ethinyl Estradiol 3-Methyl Ether, (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-2(7),3,5-trien-14-ol, (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo(8.7.0.02,7.011,15)heptadeca-2(7),3,5-trien-14-ol, (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-14-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, (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, (8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta(a)phenanthren-17-ol, (8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta(a)phenanthren-17-ol, (8S,9S,13S,14S,17S)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta(a)phenanthren-17-ol, (8S,9S,13S,14S,17S)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol, Ethynyloestradiol methyl ether, MESTRANOL COMPONENT OF ENOVID, MESTRANOL COMPONENT OF OVULEN, 17a-Ethynylestradiol 3-Methyl Ether, 3-Mmethoxy-17alpha-ethynyloestradiol, 17alpha-Ethynyloestradiol methyl ether, 17alha-Ethinyloestradiol 3-methyl ether, 17a-Ethynyl-3-methoxy-1,3,5(10)-estratrien-17b-ol, (17b)-17-ethynyl-3-methoxyestra-1,3,5(10)-trien-17-ol, (17a)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol, 17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether, 3-METHOXY-19-NOR-17ALPHA-PREGNA-1,3,5(10)-TRIEN-20-YN-17-OL., 200-777-8, 33355, Menophase, Norquen, Ovastol, Devocin, 3-Methoxyethynylestradiol, EE(sub3)ME, Ethynylestradiol methyl ether, 3-Methylethynylestradiol, 3-O-Methylethynylestradiol, Compound 33355, Inostral, 3-Methylethynyloestradiol, 3-Methoxyethynyloestradiol, SC 4725, 17-Ethynyloestradiol 3-methyl ether, component of Norinyl, component of Ortho-Novum, Ethinylestradiol 3-methyl ether, Ethinyloestradiol 3-methyl ether, Ethynyloestradiol 3-methyl ether, MLS000028595, component of Ovulen, component of Norquen, delta-MVE, 17alpha-Ethynylestradiol 3-methyl ether, Inostral (steroid), Mestranolo [DCIT], NCGC00093347-02, Mestranolo, SMR000059128, (17beta)-17-ethynyl-3-(methyloxy)estra-1,3,5(10)-trien-17-ol, Mestranolum [INN-Latin], Caswell No. 547A, .delta.-MVE, 17alpha-Ethinyl estradiol 3-methyl ether, 17-Ethynyl-3-methoxyestra-1,3,5(10)-trien-17-ol, 3-Methoxy-17alpha-ethinylestradiol, 3-Methoxy-17alpha-ethinyloestradiol, 3-Methoxy-17alpha-ethynyloestradiol, 3-Methoxy-17-alpha-ethinylestradiol, 3-Methoxy-17-alpha-ethynylestradiol, 17alpha-Ethynylestradiol methyl ether, 3-Methoxy-17-alpha-ethinyloestradiol, 3-Methoxy-17-alpha-ethynyloestradiol, CCRIS 377, 17-alpha-Ethynyloestradiol methyl ether, 17alpha-Ethinylestradiol 3-methyl ether, 8027 C. B., 17alpha-Ethynyloestradiol 3-methyl ether, 3-Methoxy-17-ethynyloestradiol-17-beta, Mestranol [Steroidal oestrogens], 17alpha-Ethinyl oestradiol 3-methyl ether, HSDB 3588, 17-alpha-Ethinyl estradiol 3-methyl ether, 17-alpha-Ethinyl oestradiol 3-methyl ether, EINECS 200-777-8, NSC 84032, EPA Pesticide Chemical Code 115401, 17beta-Estradiol, 17-ethynyl-, 3-(methyl ether), BRN 2625905, UNII-B2V233XGE7, NSC84032, 17-Ethynyl-3-methoxy-1,3,5(10)-oestratien-17-beta-ol, AI3-51798, 3-Methoxy-17alpha-ethynyl-1,3,5(10)-estratrien-17beta-ol, 3-Methoxy-17alpha-ethynyl-1,3,5(10)-oestratrien-17beta-ol, 17-alpha-Ethynyl-3-methoxy-1,3,5(10)-estratrien-17-beta-ol, 3-Methoxy-17-alpha-ethynyl-1,3,5(10)-estratrien-17-beta-ol, 3-Methoxy-17-alpha-ethynyl-1,3,5(10)-oestratrien-17-beta-ol, CAS-72-33-3, 3-Methoxy-17-alpha-19-norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-Methoxy-19-nor-17-alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, Prestwick_966, Mestranol, 99%, Mestranol (Standard), Mestranol [USAN:USP:INN:BAN:JAN], Estra-1,3,5(10)-trien-17beta-ol, 17-ethynyl-3-methoxy-, Opera_ID_872, 17alpha-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, Estra-1,3,5(10)-trien-17-beta-ol, 17-alpha-ethynyl-3-methoxy-, Prestwick0_000846, Prestwick1_000846, Prestwick2_000846, Prestwick3_000846, (+)-17-alpha-Ethynyl-17-beta-hydroxy-3-methoxy-1,3,5(10)-estratriene, (17-alpha)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol, 17-ethynyl-3-methoxyestra-1(10),2,4-trien-17-ol, (+)-17-alpha-Ethynyl-17-beta-hydroxy-3-methoxy-1,3,5(10)-oestratriene, 17-alpha-Ethynyl-3-methoxy-17-beta-hydroxy-delta-1,3,5(10)-estratriene, 17-alpha-Ethynyl-3-methoxy-17-beta-hydroxy-delta-1,3,5(10)-oestratriene, 3,17-beta-Dihydroxy-17-alpha-ethynyl-1,3,5(10)-estratriene-3-methyl ether, SCHEMBL41391, BSPBio_000831, MLS001077321, MLS001424224, BIDD:ER0199, SPBio_002752, Mestranol (JP18/USP/INN), BPBio1_000915, ethynylestradiol-3-methyl ether, GTPL7087, CHEMBL1201151, HY-B0390R, MSK8586, IMSSROKUHAOUJS-MJCUULBUSA-N, HMS1570J13, HMS2051J22, HMS2097J13, HMS2230L20, HMS3714J13, HY-B0390, Tox21_111200, Tox21_301837, 17-alpha-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, 19-Nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, SBB066071, AKOS005267152, Tox21_111200_1, CCG-101067, DB01357, FM25119, NC00317, NCGC00093347-03, NCGC00093347-05, NCGC00093347-07, NCGC00179410-01, NCGC00255342-01, AC-13293, AS-56063, NS00009656, S2125, Mestranol, VETRANAL(TM), analytical standard, C07618, C76306, D00575, Q904308, SR-01000695429, SR-01000695429-4, BRD-K31920458-001-03-8, BRD-K31920458-001-23-6, Z1557501642, Mestranol, European Pharmacopoeia (EP) Reference Standard, Mestranol, United States Pharmacopeia (USP) Reference Standard, 17.Alpha.-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-meth, (+ )-17.alpha.-Ethynyl-17.beta.-hydroxy-3-methoxy-1,3, 5(10)-oestratriene, (+)-17.alpha.-Ethynyl-17.beta.-hydroxy-3-methoxy-1,3, 5(10)-estratriene, (17a)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol;17a-Ethynyl-3-methoxy-17b-hydroxy-1,3,5(10)-estratriene;3-Methoxy-17a-ethyn ylestradiol, (1S,11S,15S,10R,14R)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0.0]heptadeca-2(7),3,5-trien-14-ol, (8R,13S,17R)-17-Ethynyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol

Mestranol is primarily used as an estrogenic component in combined oral contraceptives and hormone replacement therapies. It is also employed in research studies investigating estrogen receptor interactions and hormonal regulation. Additionally, Mestranol serves as a reference standard in analytical chemistry for quality control and method validation. Its applications extend to preclinical studies exploring the effects of synthetic estrogens on metabolic and reproductive systems.

Safety and Hazards

GHS Hazard Statements

• H302 (20%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (20%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (45.9%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (45.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (20%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]
• H360 (48.2%): May damage fertility or the unborn child [Danger Reproductive toxicity]
• H362 (28.2%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]

Precautionary Statements

• P203, P260, P261, P263, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (20%)
• Acute Tox. 4 (20%)
• Skin Irrit. 2 (45.9%)
• Eye Irrit. 2 (45.9%)
• Acute Tox. 4 (20%)
• Carc. 2 (100%)
• Repr. 1B (48.2%)
• Lact. (28.2%)

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