Estrin (compound)

Estrin (compound)
Names
IUPAC name
(8S,9S,13S,14S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene
Other names
Estra-1,3,5(10)-triene; Estratriene
Identifiers
3D model (JSmol)
ChemSpider
Properties
C18H24
Molar mass 240.39 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Estrin (American English), or oestrin (British English), also known as estra-1,3,5(10)-triene, is an estrane steroid. It is dehydrogenated estrane with double bonds specifically at the C1, C3, and C5(10) positions. Estrin is a parent structure of the estrogen steroid hormones estradiol, estrone, and estriol, which have also been known as dihydroxyestrin, ketohydroxyestrin, and trihydroxyestrin, respectively.[1][2] Unlike its estrogen derivatives, estrin itself does not possess estrogenic activity, as hydroxyl and/or keto substitutions at the C3 and C17 positions are critical for binding affinity to the estrogen receptors.[3]

The term estrin is also a synonym for estrogen.[4] It was coined by Sir Alan S. Parkes and C. W. Bellerby in 1926 to describe the hormone secreted from the ovaries that induces estrus in animals (i.e., estrogen).[4]

See also

References

  1. ↑ Biskind, Morton S. (1935). "COMMERCIAL GLANDULAR PRODUCTS". Journal of the American Medical Association. 105 (9): 667. ISSN 0002-9955. doi:10.1001/jama.1935.92760350007009a.
  2. ↑ Fluhmann CF (1938). "Estrogenic Hormones: Their Clinical Usage". Cal West Med. 49 (5): 362–6. PMC 1659459 Freely accessible. PMID 18744783.
  3. ↑ Anstead GM, Carlson KE, Katzenellenbogen JA (1997). "The estradiol pharmacophore: ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site". Steroids. 62 (3): 268–303. PMID 9071738.
  4. 1 2 Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 750–. ISBN 978-1-4511-4847-3.



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