에스트론

에스트론
이름
	IUPAC 이름 (8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
	별칭 Oestrone; E1; 3-Hydroxyestra-1,3,5(10)-trien-17-one
식별자
CAS 번호	53-16-7 ;
3D 모델 (JSmol)	Interactive image;
ChEBI	CHEBI:17263 ;
ChEMBL	ChEMBL1405 ;
ChemSpider	5660 ;
ECHA InfoCard	100.000.150
KEGG	D00067 ;
PubChem CID	5870;
UNII	2DI9HA706A ;
CompTox Dashboard (EPA)	DTXSID4022367 ;
	InChI InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1 Key: DNXHEGUUPJUMQT-CBZIJGRNSA-N ;
	SMILES O=C4[C@]3(CC[C@@H]2c1ccc(O)cc1CC[C@H]2[C@@H]3CC4)C;
성질
화학식	C18H22O2
몰 질량	270.366 g/mol
녹는점	254.5
	달리 명시된 경우를 제외하면, 표준상태(25 °C [77 °F], 100 kPa)에서 물질의 정보가 제공됨. 정보상자 각주

에스트론(Estrone, E1, oestrone)은 스테로이드, 약에스트로겐, 여성 성 호르몬이다.^[1] 에스트라디올, 에스트리올과 함께 주된 3가지 내인성 에스트로겐 가운데로 하나이다.^[1] 다른 에스트로겐과 마찬가지로 에스트론은 콜레스테롤로부터 합성되며 생식샘에서 주로 분비되지만 지방 조직 내의 부신 안드로겐으로부터 형성될 수도 있다.^[2] 에스트라디올과 비교하자면, 에스트론과 에스트리올 모두 에스트로겐으로서 훨씬 활동력이 약한 편이다.^[1] 에스트론은 에스트라디올로 변환될 수 있으며 주로 에스트라디올의 전구체나 대사 중간 생성물의 역할을 한다.^[1]^[3]

자연 호르몬의 역할 외에도 에스트론은 이를테면 호르몬 대체요법을 위해 의약품으로 사용되고 있다. 에스트론의 약물 이용과 관련해서는 에스트론 (약물) 문서를 참고할 것.

역사 편집

에스트론은 최초로 발견된 스테로이드 호르몬이었다.^[4]^[5] 미국의 과학자 에드워드 도이지와 에드거 알렌(Edgar Allen), 독일의 생화학자 아돌프 부테난트에 의해 독립적으로 1929년 발견되었으나 도이지와 알렌은 부테난트에 앞서 2개월 전 분리하였다.^[4]^[6]^[7] 이들은 임신한 여성의 소변으로부터 결정 형태로 에스트론을 분리시켜 정제하였다.^[6]^[7]^[8]

각주 편집

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미디어 분류가 있습니다.

에스트론

↑ ^가 ^나 ^다 ^라 Kuhl H (August 2005). “Pharmacology of estrogens and progestogens: influence of different routes of administration” (PDF). 《Climacteric》. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947.
↑ Hornstein T, Schwerin JL (2012년 1월 1일). 《Biology of Women》. Cengage Learning. 369–쪽. ISBN 978-1-285-40102-7.
↑ van Keep PA, Utian WH, Vermeulen A (2012년 12월 6일). 《The Controversial Climacteric: The workshop moderators' reports presented at the Third International Congress on the Menopause, held in Ostend, Belgium, in June 1981, under the auspices of the International Menopause Society》. Springer Science & Business Media. 92쪽. ISBN 978-94-011-7253-0.
↑ ^가 ^나 Vern L. Bullough (1995년 5월 19일). 《Science In The Bedroom: A History Of Sex Research》. Basic Books. 128–쪽. ISBN 978-0-465-07259-0. When Allen and Doisy heard about the [Ascheim-Zondek test for the diagnosis of pregnancy], they realized there was a rich and easily handled source of hormones in urine from which they could develop a potent extract. [...] Allen and Doisy's research was sponsored by the committee, while that of their main rival, Adolt Butenandt (b. 1903) of the University of Gottingen was sponsored by a German pharmaceutical firm. In 1929, both terms announced the isolation of a pure crystal female sex hormone, estrone, in 1929, although Doisy and Allen did so two months earlier than Butenandt.27 By 1931, estrone was being commercially produced by Parke Davis in this country, and Schering-Kahlbaum in Germany. Interestingly, when Butenandt (who shared the Nobel Prize for chemistry in 1939) isolated estrone and analyzed its structure, he found that it was a steroid, the first hormone to be classed in this molecular family. ^{[깨진 링크(과거 내용 찾기)]}
↑ Nielsch U, Fuhrmann U, Jaroch S (2016년 3월 30일). 《New Approaches to Drug Discovery》. Springer. 7–쪽. ISBN 978-3-319-28914-4. The first steroid hormone was isolated from the urine of pregnant women by Adolf Butenandt in 1929 (estrone; see Fig. 1) (Butenandt 1931).
↑ ^가 ^나 Fritz F. Parl (2000). 《Estrogens, Estrogen Receptor and Breast Cancer》. IOS Press. 4–5쪽. ISBN 978-0-9673355-4-4. [Doisy] focused his research on the isolation of female sex hormones from hundreds of gallons of human pregnancy urine based on the discovery by Ascheim and Zondeck in 1927 that the urine of pregnant women possessed estrogenic activity [9]. In the summer of 1929, Doisy succeeded in the isolated of estrone (named by him theelin), simultaneously with but independent of Adolf Butenandt of the University of Gottingen in Germany. Doisy presented his results on the crystallization of estrone at the XIII International Physiological Congress in Boston in August 1929 [10].
↑ ^가 ^나 James K. Laylin (1993년 10월 30일). 《Nobel Laureates in Chemistry, 1901–1992》. Chemical Heritage Foundation. 255–쪽. ISBN 978-0-8412-2690-6. Adolt Friedrich Johann Butenandt was awarded the Nobel Prize in chemistry in 1939 "for his work on sex hormones"; [...] In 1929 Butenandt isolated estrone [...] in pure crystalline form. [...] Both Butenandt and Edward Doisy isolated estrone simultaneously but independently in 1929. [...] Butenandt took a big step forward in the history of biochemistry when he isolated estrone from the urine of pregnant women. [...] He named it "progynon" in his first publication, and then "folliculine", [...] By 1932, [...] he could determine its chemical structure, [...]
↑ Arthur Greenberg (2014년 5월 14일). 《Chemistry: Decade by Decade》. Infobase Publishing. 127–쪽. ISBN 978-1-4381-0978-7. Rational chemical studies of human sex hormones began in 1929 with Adolph Butenandt's isolation of pure crystalline estrone, the follicular hormone, from the urine of pregnant women. [...] Butenandt and Ruzicka shared the 1939 Nobel Prize in chemistry.

[pmid16112947-1] 가 ^나 ^다 ^라 Kuhl H (August 2005). “Pharmacology of estrogens and progestogens: influence of different routes of administration” (PDF). 《Climacteric》. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947.

[HornsteinSchwerin2012-2] Hornstein T, Schwerin JL (2012년 1월 1일). 《Biology of Women》. Cengage Learning. 369–쪽. ISBN 978-1-285-40102-7.

[KeepUtian2012-3] van Keep PA, Utian WH, Vermeulen A (2012년 12월 6일). 《The Controversial Climacteric: The workshop moderators' reports presented at the Third International Congress on the Menopause, held in Ostend, Belgium, in June 1981, under the auspices of the International Menopause Society》. Springer Science & Business Media. 92쪽. ISBN 978-94-011-7253-0.

[Bullough1995-4] 가 ^나 Vern L. Bullough (1995년 5월 19일). 《Science In The Bedroom: A History Of Sex Research》. Basic Books. 128–쪽. ISBN 978-0-465-07259-0. When Allen and Doisy heard about the [Ascheim-Zondek test for the diagnosis of pregnancy], they realized there was a rich and easily handled source of hormones in urine from which they could develop a potent extract. [...] Allen and Doisy's research was sponsored by the committee, while that of their main rival, Adolt Butenandt (b. 1903) of the University of Gottingen was sponsored by a German pharmaceutical firm. In 1929, both terms announced the isolation of a pure crystal female sex hormone, estrone, in 1929, although Doisy and Allen did so two months earlier than Butenandt.27 By 1931, estrone was being commercially produced by Parke Davis in this country, and Schering-Kahlbaum in Germany. Interestingly, when Butenandt (who shared the Nobel Prize for chemistry in 1939) isolated estrone and analyzed its structure, he found that it was a steroid, the first hormone to be classed in this molecular family. ^{[깨진 링크(과거 내용 찾기)]}

[NielschFuhrmann2016-5] Nielsch U, Fuhrmann U, Jaroch S (2016년 3월 30일). 《New Approaches to Drug Discovery》. Springer. 7–쪽. ISBN 978-3-319-28914-4. The first steroid hormone was isolated from the urine of pregnant women by Adolf Butenandt in 1929 (estrone; see Fig. 1) (Butenandt 1931).

[Parl2000-6] 가 ^나 Fritz F. Parl (2000). 《Estrogens, Estrogen Receptor and Breast Cancer》. IOS Press. 4–5쪽. ISBN 978-0-9673355-4-4. [Doisy] focused his research on the isolation of female sex hormones from hundreds of gallons of human pregnancy urine based on the discovery by Ascheim and Zondeck in 1927 that the urine of pregnant women possessed estrogenic activity [9]. In the summer of 1929, Doisy succeeded in the isolated of estrone (named by him theelin), simultaneously with but independent of Adolf Butenandt of the University of Gottingen in Germany. Doisy presented his results on the crystallization of estrone at the XIII International Physiological Congress in Boston in August 1929 [10].

[Laylin1993-7] 가 ^나 James K. Laylin (1993년 10월 30일). 《Nobel Laureates in Chemistry, 1901–1992》. Chemical Heritage Foundation. 255–쪽. ISBN 978-0-8412-2690-6. Adolt Friedrich Johann Butenandt was awarded the Nobel Prize in chemistry in 1939 "for his work on sex hormones"; [...] In 1929 Butenandt isolated estrone [...] in pure crystalline form. [...] Both Butenandt and Edward Doisy isolated estrone simultaneously but independently in 1929. [...] Butenandt took a big step forward in the history of biochemistry when he isolated estrone from the urine of pregnant women. [...] He named it "progynon" in his first publication, and then "folliculine", [...] By 1932, [...] he could determine its chemical structure, [...]

[Greenberg2014-8] Arthur Greenberg (2014년 5월 14일). 《Chemistry: Decade by Decade》. Infobase Publishing. 127–쪽. ISBN 978-1-4381-0978-7. Rational chemical studies of human sex hormones began in 1929 with Adolph Butenandt's isolation of pure crystalline estrone, the follicular hormone, from the urine of pregnant women. [...] Butenandt and Ruzicka shared the 1939 Nobel Prize in chemistry.

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