Hippulin

Hippulin
Clinical data
Other names	Δ8-14-Isoestrone; 8-Dehydro-14-isoestrone; 14-Isoestra-1,3,5(10),8-tetraen-3-ol-17-one
Routes of; administration	By mouth
Drug class	Estrogen
Identifiers
	IUPAC name (13S,14R)-3-hydroxy-13-methyl-7,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one;
PubChem CID	6451472;
ChemSpider	4953937;
Chemical and physical data
Formula	C18H20O2
Molar mass	268.356 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CCC3=C([C@@H]1CCC2=O)CCc4c3ccc(c4)O;
	InChI InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,16,19H,2,4,6-9H2,1H3/t16-,18-/m0/s1; Key:OUGSRCWSHMWPQE-WMZOPIPTSA-N;

Hippulin, also known as Δ⁸-14-isoestrone, as well as 14-isoestra-1,3,5(10),8-tetraen-3-ol-17-one, is a naturally occurring estrogen found in horses and an isomer of equilin.[1][2][3][4] The compound, likely in sodium sulfate form, is a component of conjugated estrogens (Premarin), a pharmaceutical extract of the urine of pregnant mares,[1][2][3] though it is present only in small amounts in pregnant mare urine.[5] It has been reported by possess either equivalent estrogenic activity to that of equilin or only slight estrogenic activity.[3] The compound was first described in 1932.[4][3]

References

C. W. Emmens (22 October 2013). Hormone Assay. Elsevier Science. pp. 391–. ISBN 978-1-4832-7286-3.
H.J. Buchsbaum (6 December 2012). The Menopause. Springer Science & Business Media. pp. 56–. ISBN 978-1-4612-5525-3.
Banes D, Carol J, Haenni EO (1950). "The resolution of isoequilin A and the identification of compound 3" (PDF). J. Biol. Chem. 187 (2): 557–70. PMID 14803438.
Girard, H., Sandulesco, G., Fridenson, A., Gaudefroy, C., & Rutgers, J. J. (1932). Sur les Hormones Sexuelles Cristallisées Retirées de l'Urine des Juments Gravides. Compt. Rend. Acad. Sci, 194, 1020.
Wintersteiner, O. (1937). "Estrogenic Diols from the Urine of Pregnant Mares". Cold Spring Harbor Symposia on Quantitative Biology. 5 (0): 25–33. doi:10.1101/SQB.1937.005.01.003. ISSN 0091-7451.

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[Emmens2013-1] C. W. Emmens (22 October 2013). Hormone Assay. Elsevier Science. pp. 391–. ISBN 978-1-4832-7286-3.

[Buchsbaum2012-2] H.J. Buchsbaum (6 December 2012). The Menopause. Springer Science & Business Media. pp. 56–. ISBN 978-1-4612-5525-3.

[pmid14803438-3] Banes D, Carol J, Haenni EO (1950). "The resolution of isoequilin A and the identification of compound 3" (PDF). J. Biol. Chem. 187 (2): 557–70. PMID 14803438.

[Girard1932-4] Girard, H., Sandulesco, G., Fridenson, A., Gaudefroy, C., & Rutgers, J. J. (1932). Sur les Hormones Sexuelles Cristallisées Retirées de l'Urine des Juments Gravides. Compt. Rend. Acad. Sci, 194, 1020.

[Wintersteiner1937-5] Wintersteiner, O. (1937). "Estrogenic Diols from the Urine of Pregnant Mares". Cold Spring Harbor Symposia on Quantitative Biology. 5 (0): 25–33. doi:10.1101/SQB.1937.005.01.003. ISSN 0091-7451.

Hippulin

See also

References