Estrone

Title: Estrone
CAS Registry Number: 53-16-7
CAS Name: 3-Hydroxyestra-1,3,5(10)-trien-17-one
Additional Names: 1,3,5-estratrien-3-ol-17-one; oestrone; folliculin; follicular hormone; tokokin; thelykinin; ketohydroxyestrin
Trademarks: Hiestrone; Menformon (Organon); Glandubolin; Cristallovar; Destrone; Endofolliculina; Estrol; Femidyn; Folikrin; Kolpon (Organon); Crinovaryl; Folisan; Disynformon; Hormovarine (Clin-Comar-Byla); Oestroperos; Wynestron (Wyeth); Thelestrin (Carnrick); Kestrone (Cooper); Estrusol (Cooper); Estrugenone (Kremers-Urban); Femestrone Inj; Folipex; Follestrine; Follidrin (tablets); Follicunodis; Hormofollin; Oestrin; Ovifollin; Perlatan; Ketodestrin; Theelin (Parke-Davis)
Molecular Formula: C18H22O2
Molecular Weight: 270.37
Percent Composition: C 79.96%, H 8.20%, O 11.84%
Literature References: A metabolite of 17b-estradiol, q.v., possessing considerably less biological activity; isolated as d-form. Occurs in pregnancy urine of women and mares, in follicular liquor of many animals, in human placenta, in urine of bulls and stallions, in palm-kernel oil. Isoln: Butenandt, Naturwissenschaften 17, 879 (1929); Doisy et al., Am. J. Physiol. 90, 329 (1929). Also isolated from moghat roots and date palm pollen grains: Amin et al., Phytochemistry 8, 295 (1969). Manuf: E. A. Doisy et al., US 1967350, US 1967351 (1934 both to St. Louis University); Joly et al., FR 1305992 (1962 to Roussel-Uclaf). Synthesis of a stereoisomer of estrone: W. E. Bachmann et al., J. Am. Chem. Soc. 64, 974 (1942). Total synthesis of natural estrone: G. Anner, K. Miescher, Helv. Chim. Acta 31, 2173 (1948); 32, 1957 (1949); 33, 1379 (1950); W. S. Johnson et al., J. Am. Chem. Soc. 72, 1426 (1950); 74, 2832 (1952); I. V. Torgov et al., Dokl. Akad. Nauk SSSR 135, 73 (1960), C.A. 55, 11462f (1961). Stereochemistry of estrone isomers: W. S. Johnson et al., J. Am. Chem. Soc. 80, 661 (1958). Review of estrone syntheses: L. F. Fieser, M. Fieser, Steroids (Reinhold, New York, 1959) pp 495-502; T. B. Windholz, M. Windholz, Angew. Chem. Int. Ed. 3, 353 (1964); Taub, "Naturally Occurring Aromatic Steroids" in The Total Synthesis of Natural Products vol. 2, J. ApSimon, Ed. (John Wiley & Sons, New York, 1973) pp 670-725. Recent syntheses: P. A. Bartlett, W. S. Johnson, J. Am. Chem. Soc. 95, 7501 (1973); S. Danishefsky, P. Cain, ibid. 98, 4975 (1976); T. Kametani et al., ibid. 99, 3461 (1977); P. A. Grieco et al., J. Org. Chem. 45, 2247 (1980). Comprehensive description: D. Both, Anal. Profiles Drug Subs. 12, 135-189 (1983).
Properties: Crystals from acetone, mp 254.5-256°. [a]D22 +152° (c = 0.995 in CHCl3). uv max (p-dioxane): 282, 296 nm (e 2300, 2130); (conc H2SO4): 300, 450 nm; (0.1M NaOH): 239, 293 nm. Exists in three cryst phases, one monoclinic, the other two orthorhombic. Pptd by digitonin. Soly in water (25°): 0.003 g/100 ml. One gram of estrone dissolves in 250 ml of 96% alcohol at 15°, in 50 ml of boiling alcohol; in 50 ml acetone at 15°, in 110 ml chloroform at 15°, in 145 ml boiling benzene. Sol in dioxane, pyridine, fixed alkali hydroxide solns; slightly sol in ether, vegetable oils.
Melting point: mp 254.5-256°
Optical Rotation: [a]D22 +152° (c = 0.995 in CHCl3)
Absorption maximum: uv max (p-dioxane): 282, 296 nm (e 2300, 2130); (conc H2SO4): 300, 450 nm; (0.1M NaOH): 239, 293 nm
Derivative Type: Acetate
CAS Registry Number: 901-93-9
Trademarks: Hogival
Molecular Formula: C20H24O3
Molecular Weight: 312.40
Percent Composition: C 76.89%, H 7.74%, O 15.36%
Properties: Crystals from alcohol, mp 125-127°.
Melting point: mp 125-127°
Derivative Type: Propionate
CAS Registry Number: 975-64-4
Molecular Formula: C21H26O3
Molecular Weight: 326.43
Percent Composition: C 77.27%, H 8.03%, O 14.70%
Properties: mp 134-135°, US 2156599.
Melting point: mp 134-135°
Derivative Type: Sulfate
CAS Registry Number: 481-97-0
Trademarks: Conjugol
Literature References: Price, US 2917522 (1959 to Parke, Davis).
Derivative Type: Sulfate piperazine salt
CAS Registry Number: 7280-37-7
Additional Names: Estropipate; piperazine estrone sulfate
Trademarks: Harmogen (Abbott); Ogen (Abbott); Sulestrex Piperazine (Abbott)
Molecular Formula: C22H32N2O5S
Molecular Weight: 436.56
Percent Composition: C 60.53%, H 7.39%, N 6.42%, O 18.32%, S 7.34%
Literature References: Comprehensive description: Z. L. Chang, Anal. Profiles Drug Subs. 5, 375-402 (1976).
Properties: Cryst powder, melts at 190° to a liquid which resolidifies and then decomp at 245°. [a]D25 +87.8° (c = 1 in 0.4% NaOH). uv max (0.04% NaOH): 275, 268 nm (e 838, 851).
Optical Rotation: [a]D25 +87.8° (c = 1 in 0.4% NaOH)
Absorption maximum: uv max (0.04% NaOH): 275, 268 nm (e 838, 851)
Derivative Type: dl-Form
CAS Registry Number: 19973-76-3
Properties: Crystals from acetone, mp 251-254°.
Melting point: mp 251-254°
Derivative Type: Methyl ether
CAS Registry Number: 1091-94-7
Molecular Formula: C19H24O2
Molecular Weight: 284.39
Percent Composition: C 80.24%, H 8.51%, O 11.25%
Literature References: Synthesis: T. A. Bryson, C. J. Reichel, Tetrahedron Lett. 21, 2381 (1980).
Properties: dl-Form, crystals from acetone + methanol, mp 143.2-144.2°. d-Form, crystals from methanol, mp 164-165°.
Melting point: mp 143.2-144.2°; mp 164-165°
CAUTION: These substances are listed as known human carcinogens: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-115.
Use: In the prepn of commercial 19-norsteroids.
Therap-Cat: Estrogen.
Therap-Cat-Vet: Estrogen.
Keywords: Estrogen; Steroidal.
Etafedrine Etafenone Etamiphyllin Etamycin Etanercept

Estrone
Estron.svg
Estrona3D.png
Systematic (IUPAC) name
(8R,9S,13S,14S)-3-hydroxy-13-methyl- 6,7,8,9,11,12,13,14,15,16- decahydrocyclopenta[a]phenanthren- 17- one
Clinical data
Legal status -only (US)
Pharmacokinetic data
Protein binding >95%
Half-life 19 hours
Identifiers
CAS number 53-16-7 YesY
ATC code G03CA07 G03CC04
PubChem CID 5870
IUPHAR ligand 2818
DrugBank DB00655
ChemSpider 5660 YesY
UNII 2DI9HA706A YesY
KEGG D00067 N
ChEBI CHEBI:17263 N
ChEMBL CHEMBL1405 N
Chemical data
Formula C18H22O2 
Mol. mass 270.366 g/mol
Physical data
Melt. point 254.5 °C (490 °F)
 N (what is this?)  (verify)

Estrone (E1, and also oestrone) is an estrogenic hormone secreted by the ovary as well as adipose tissue with the chemical name of 3-hydroxyestra-1,3,5(10)-triene-17-one and the chemical formula C18H22O2. Estrone is an odorless, solid crystalline powder, white in color with a melting point of 254.5 °C and a specific gravity of 1.23.[1][2][3] Estrone is one of several natural estrogens, which also include estriol and estradiol. Estrone is the least abundant of the three hormones; estradiol is present almost always in the reproductive female body, and estriol is abundant primarily during pregnancy.

Estrone is known to be a carcinogen for human females as well as cause breast tenderness or pain, nausea, headache, hypertension, and leg cramps.[1][4] In men, estrone has been known to cause anorexia, nausea, vomiting, and erectile disfunction.[2] Estrone is relevant to health and disease states because of its conversion to estrone sulfate, a long-lived derivative. Estrone sulfate acts as a reservoir that can be converted as needed to the more active estradiol. It is the predominant estrogen in postmenopausal women.[5]