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Estratetraenol

January 01, 1970

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]

Estratetraenol
Clinical data
Other namesEstra-1,3,5(10),16-tetraen-3-ol
ATC code
  • None
Identifiers
  • (8S,9S,13R,14S)-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-3-ol
CAS Number
  • 1150-90-9 Y
PubChem CID
  • 101988
ChemSpider
  • 92135
UNII
  • 4QD0FTG3VT
ChEBI
  • CHEBI:62849
CompTox Dashboard (EPA)
  • DTXSID80921587
Chemical and physical data
FormulaC18H22O
Molar mass254.373 g·mol−1
3D model (JSmol)
  • Interactive image
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=C3C=CC(=C4)O
  • 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)

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.

Experiments edit

Experiments performed have indicated a correlation between estratetraenol and the ability to attract cooperative mates. The hormone sends olfactory signals of high fertility in pregnant and ovulating women that presents and highlights attractive qualities in those women to potential mates. These interactions between the hormone signals and males showed an increased cooperation and compassion from males to the pregnant female.[10]

Another study shows that the hormone can have an effect on how a male will approach the pursuance of a female by altering the level of sexual cognition and behavior. While the hormone increases the attractions of males to females, studies also show that it does not have an effect on the impulsive sexual nature of men when it relates to sexual desire and delayed gratification.[11]

See also edit

References edit

  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.
  10. ^ Oren C, Shamay-Tsoory SG (March 2019). "Women's fertility cues affect cooperative behavior: Evidence for the role of the human putative chemosignal estratetraenol". Psychoneuroendocrinology. 101: 50–59. doi:10.1016/j.psyneuen.2018.10.028. PMID 30408723. S2CID 53217847.
  11. ^ Wu Y, Wei R, Ou J, Shen B, Ye Y (November 2022). "Estratetraenol increases preference for large sexual reward but not impulsivity among heterosexual males". Hormones and Behavior. 146: 105266. doi:10.1016/j.yhbeh.2022.105266. hdl:10397/95794. PMID 36152381. S2CID 252432682.
 

This biochemistry article is a stub. You can help Wikipedia by expanding it.

January 01, 1970
estratetraenol, also, known, estra, tetraen, endogenous, steroid, found, women, that, been, described, having, pheromone, like, activities, primates, including, humans, synthesized, from, androstadienone, aromatase, likely, ovaries, related, estrogen, hormones. 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 EstratetraenolClinical dataOther namesEstra 1 3 5 10 16 tetraen 3 olATC codeNoneIdentifiersIUPAC name 8S 9S 13R 14S 13 methyl 6 7 8 9 11 12 14 15 octahydrocyclopenta a phenanthren 3 olCAS Number1150 90 9 YPubChem CID101988ChemSpider92135UNII4QD0FTG3VTChEBICHEBI 62849CompTox Dashboard EPA DTXSID80921587Chemical and physical dataFormulaC 18H 22OMolar mass254 373 g mol 13D model JSmol Interactive imageSMILES C C 12CC C H 3 C H C H 1CC C2 CCC4 C3C CC C4 OInChI 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 s1Key CRMOMCHYBNOFIV BDXSIMOUSA N verify 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 C17b hydroxyl group has been removed and a double bond has been formed between the C16 and C17 positions Experiments editExperiments performed have indicated a correlation between estratetraenol and the ability to attract cooperative mates The hormone sends olfactory signals of high fertility in pregnant and ovulating women that presents and highlights attractive qualities in those women to potential mates These interactions between the hormone signals and males showed an increased cooperation and compassion from males to the pregnant female 10 Another study shows that the hormone can have an effect on how a male will approach the pursuance of a female by altering the level of sexual cognition and behavior While the hormone increases the attractions of males to females studies also show that it does not have an effect on the impulsive sexual nature of men when it relates to sexual desire and delayed gratification 11 See also editList of neurosteroids Pheromones and pherinesReferences edit 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 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 Jacob S Hayreh DJ McClintock MK 2001 Context dependent effects of steroid chemosignals on human physiology and mood Physiology amp Behavior 74 1 2 15 27 doi 10 1016 S0031 9384 01 00537 6 PMID 11564447 S2CID 19312085 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 Berglund H Lindstrom 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 Berglund H Lindstrom 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 Weusten JJ 1989 Biochemical pathways in human testicular steroidogenesis PDF Ph D thesis Pressa Trajectina 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 Lundstrom 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 Oren C Shamay Tsoory SG March 2019 Women s fertility cues affect cooperative behavior Evidence for the role of the human putative chemosignal estratetraenol Psychoneuroendocrinology 101 50 59 doi 10 1016 j psyneuen 2018 10 028 PMID 30408723 S2CID 53217847 Wu Y Wei R Ou J Shen B Ye Y November 2022 Estratetraenol increases preference for large sexual reward but not impulsivity among heterosexual males Hormones and Behavior 146 105266 doi 10 1016 j yhbeh 2022 105266 hdl 10397 95794 PMID 36152381 S2CID 252432682 nbsp This biochemistry article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Estratetraenol amp oldid 1189885602, wikipedia, wiki, book, books, library,

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