Hippulin

Hippulin
Clinical data
Other namesΔ8-14-Isoestrone; 8-Dehydro-14-isoestrone; 14-Isoestra-1,3,5(10),8-tetraen-3-ol-17-one
Routes of
administration		By mouth
Drug classEstrogen
Identifiers
  • (13S,14R)-3-hydroxy-13-methyl-7,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H20O2
Molar mass268.356 g·mol−1
3D model (JSmol)
  • C[C@]12CCC3=C([C@@H]1CCC2=O)CCc4c3ccc(c4)O
  • 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]

  1. ^ a b C. W. Emmens (22 October 2013). Hormone Assay. Elsevier Science. pp. 391–. ISBN 978-1-4832-7286-3.
  2. ^ a b H.J. Buchsbaum (6 December 2012). The Menopause. Springer Science & Business Media. pp. 56–. ISBN 978-1-4612-5525-3.
  3. ^ a b c d 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. doi:10.1016/S0021-9258(18)56200-1. PMID 14803438.
  4. ^ a b 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.
  5. ^ Wintersteiner, O. (1937). "Estrogenic Diols from the Urine of Pregnant Mares". Cold Spring Harbor Symposia on Quantitative Biology. 5: 25–33. doi:10.1101/SQB.1937.005.01.003. ISSN 0091-7451. S2CID 81202266.