Estratetraenol

Estratetraenol
Clinical data
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 ;
PubChem CID	101988;
ChemSpider	92135;
ChEBI	CHEBI:62849;
CompTox Dashboard (EPA)	DTXSID80921587 ;
Chemical and physical data
Formula	C18H22O
Molar mass	254.366 g/mol 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.

References

^ Thysen, B; Elliott, WH; Katzman, PA (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 (2006). "Sex-specific differences in olfactory sensitivity for putative human pheromones in nonhuman primates". Journal of Comparative Psychology. 120 (2): 106–12. 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 & Behavior. 74 (1–2): 15–27. doi:10.1016/S0031-9384(01)00537-6. PMID 11564447.
^ Savic, I; Berglund, H; Gulyas, B; Roland, P (2001). "Smelling of odorous sex hormone-like compounds causes sex-differentiated hypothalamic activations in humans". Neuron. 31 (4): 661–8. doi:10.1016/S0896-6273(01)00390-7. PMID 11545724.
^ Berglund, H; Lindström, P; Savic, I (2006). "Brain response to putative pheromones in lesbian women". Proceedings of the National Academy of Sciences of the United States of America. 103 (21): 8269–74. doi:10.1073/pnas.0600331103. PMC 1570103. PMID 16705035.
^ Berglund, H; Lindström, P; Dhejne-Helmy, C; Savic, I (2008). "Male-to-female transsexuals show sex-atypical hypothalamus activation when smelling odorous steroids". Cerebral cortex (New York, N.Y. : 1991). 18 (8): 1900–8. doi:10.1093/cercor/bhm216. PMID 18056697.
^ Joseph Johannes; Agnes Maria Weusten (1989). Biochemical pathways in human testicular steroidogenesis (PDF). Pressa Trajectina.
^ Thysen B, Elliott WH, Katzman PA (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.
^ Lundström (2005). Human pheromones : psychological and neurological modulation of a putative human pheromone. Uppsala: Acta Universitatis Upsaliensis. p. 17. ISBN 91-554-6297-9.

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[1] Thysen, B; Elliott, WH; Katzman, PA (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 (2006). "Sex-specific differences in olfactory sensitivity for putative human pheromones in nonhuman primates". Journal of Comparative Psychology. 120 (2): 106–12. 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.

[4] Savic, I; Berglund, H; Gulyas, B; Roland, P (2001). "Smelling of odorous sex hormone-like compounds causes sex-differentiated hypothalamic activations in humans". Neuron. 31 (4): 661–8. doi:10.1016/S0896-6273(01)00390-7. PMID 11545724.

[5] Berglund, H; Lindström, P; Savic, I (2006). "Brain response to putative pheromones in lesbian women". Proceedings of the National Academy of Sciences of the United States of America. 103 (21): 8269–74. doi:10.1073/pnas.0600331103. PMC 1570103. PMID 16705035.

[6] Berglund, H; Lindström, P; Dhejne-Helmy, C; Savic, I (2008). "Male-to-female transsexuals show sex-atypical hypothalamus activation when smelling odorous steroids". Cerebral cortex (New York, N.Y. : 1991). 18 (8): 1900–8. doi:10.1093/cercor/bhm216. PMID 18056697.

[JohannesWeusten1989-7] Joseph Johannes; Agnes Maria Weusten (1989). Biochemical pathways in human testicular steroidogenesis (PDF). Pressa Trajectina.

[pmid4295975-8] Thysen B, Elliott WH, Katzman PA (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.

[Lundström2005-9] Lundström (2005). Human pheromones : psychological and neurological modulation of a putative human pheromone. Uppsala: Acta Universitatis Upsaliensis. p. 17. ISBN 91-554-6297-9.

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See also

References