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Estratetraenol information


Estratetraenol
Clinical data
Other namesEstra-1,3,5(10),16-tetraen-3-ol
ATC code
  • None
Identifiers
IUPAC name
  • (8S,9S,13R,14S)-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-3-ol
CAS Number
  • 1150-90-9 checkY
PubChem CID
  • 101988
ChemSpider
  • 92135
UNII
  • 4QD0FTG3VT
ChEBI
  • CHEBI:62849
CompTox Dashboard (EPA)
  • DTXSID80921587 Edit this at Wikidata
Chemical and physical data
FormulaC18H22O
Molar mass254.373 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=C3C=CC(=C4)O
InChI
  • InChI=1S/C18H22O/c1-18-9-2-3-17(18)16-6-4-12-11-13(19)5-7-14(12)15(16)8-10-18/h2,5,7,9,11,15-17,19H,3-4,6,8,10H2,1H3/t15-,16-,17+,18+/m1/s1
  • Key:CRMOMCHYBNOFIV-BDXSIMOUSA-N
  (verify)

Estratetraenol, also known as estra-1,3,5(10),16-tetraen-3-ol, is an endogenous steroid found in women[1] that has been described as having pheromone-like activities in primates,[2] including humans.[3][4][5][6] Estratetraenol is synthesized from androstadienone by aromatase likely in the ovaries,[7] and is related to the estrogen sex hormones, yet has no known estrogenic effects. It was first identified from the urine of pregnant women.[8]

Estratetraenyl acetate, or estra-1,3,5(10),16-tetraen-3-yl acetate, is a more potent synthetic derivative of estratetraenol.[9]

Estratetraenol is an estrane (C18) steroid and an analogue of estradiol where the C17β hydroxyl group has been removed and a double bond has been formed between the C16 and C17 positions.

  1. ^ Thysen B, Elliott WH, Katzman PA (January 1968). "Identification of estra-1,3,5(10),16-tetraen-3-ol (estratetraenol) from the urine of pregnant women (1)". Steroids. 11 (1): 73–87. doi:10.1016/S0039-128X(68)80052-2. PMID 4295975.
  2. ^ Laska M, Wieser A, Salazar LT (May 2006). "Sex-specific differences in olfactory sensitivity for putative human pheromones in nonhuman primates". Journal of Comparative Psychology. 120 (2): 106–112. doi:10.1037/0735-7036.120.2.106. PMID 16719588.
  3. ^ Jacob S, Hayreh DJ, McClintock MK (2001). "Context-dependent effects of steroid chemosignals on human physiology and mood". Physiology & Behavior. 74 (1–2): 15–27. doi:10.1016/S0031-9384(01)00537-6. PMID 11564447. S2CID 19312085.
  4. ^ Savic I, Berglund H, Gulyas B, Roland P (August 2001). "Smelling of odorous sex hormone-like compounds causes sex-differentiated hypothalamic activations in humans". Neuron. 31 (4): 661–668. doi:10.1016/S0896-6273(01)00390-7. PMID 11545724. S2CID 2547202.
  5. ^ Berglund H, Lindström P, Savic I (May 2006). "Brain response to putative pheromones in lesbian women". Proceedings of the National Academy of Sciences of the United States of America. 103 (21): 8269–8274. Bibcode:2006PNAS..103.8269B. doi:10.1073/pnas.0600331103. PMC 1570103. PMID 16705035.
  6. ^ Berglund H, Lindström P, Dhejne-Helmy C, Savic I (August 2008). "Male-to-female transsexuals show sex-atypical hypothalamus activation when smelling odorous steroids". Cerebral Cortex. 18 (8): 1900–1908. doi:10.1093/cercor/bhm216. PMID 18056697.
  7. ^ Weusten JJ (1989). Biochemical pathways in human testicular steroidogenesis (PDF) (Ph.D. thesis). Pressa Trajectina.
  8. ^ Thysen B, Elliott WH, Katzman PA (January 1968). "Identification of estra-1,3,5(10),16-tetraen-3-ol (estratetraenol) from the urine of pregnant women (1)". Steroids. 11 (1): 73–87. doi:10.1016/s0039-128x(68)80052-2. PMID 4295975.
  9. ^ Lundström JN (2005). Human pheromones : psychological and neurological modulation of a putative human pheromone (Ph.D. thesis). Uppsala: Acta Universitatis Upsaliensis. p. 17. ISBN 91-554-6297-9.

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Estratetraenol

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Progesterone

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Estrogen

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Glucocorticoid

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Androgen

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Estradiol

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Pregnenolone

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Testosterone

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Mineralocorticoid

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Steroid

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Cortisone

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Steroid hormone

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Neurosteroid

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androstadienol, androstadienone, androstenol, and androstenone and the estrane estratetraenol. Certain other endogenous steroids, such as pregnenolone, progesterone...

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Aldosterone

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Pherine

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Progestogen

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C18H22O

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Androstenedione

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Androsterone

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Estriol

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List of neurosteroids

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Androstadienone

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