Estratetraenol

Estratetraenol

Systematic (IUPAC) name
(8S,9S,13R,14S)-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-3-ol
Identifiers
CAS Number	1150-90-9
ATC code	none
PubChem	CID 101988
ChemSpider	92135
ChEBI	CHEBI:62849
Chemical data
Formula	C18H22O
Molar mass	254.366 g/mol
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
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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]

See also

• Androstadienol
• Androstadienone
• Androstenone
• Androstenol
• Androsterone
• Pregna-4,20-dien-3,6-dione

References

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 (Washington, D.C. : 1983) 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.
7. Joseph Johannes; Agnes Maria Weusten (1989). Biochemical pathways in human testicular steroidogenesis (PDF). Pressa Trajectina.
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.
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.