androsterone
American Heritage Dictionary:
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an·dros·ter·one
Wiley Dictionary of Flavors:
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Androsterone
The pheromone that is found in human, dog, and porcine urine, and in certain fungi like truffles. This chemical is perceived in four different ways, with subtle variations: (a) sweet/fruity and almost grape-like; (b) camphoraceous and aromatic; (c) uriney, with sexual under-tones; or (d) odorless. Some people can perceive this compound with great intensity and others do not. The very perception of very large molecules like this is not typically accomplished through olfactory organs, but through vomeronasal nerve endings, linked to subconscious and instinctual response. The fact that dogs or boars are used to hunt truffles down is illustrative in that the vomeronasal (sexual) attraction had been exploited without knowing the presence of this compound or the reason why the technique worked. Our intense appreciation of truffles as a food could be partly due to their pleasant aroma, partly due to their rarity, and partly due to some subconscious stimulus being perceived. The four types of characters perceived by subjects exposed to androstenone might be an odor-based analogy to the response of tasters to PROP. As with PROP testing as an indicator or supertasters, perhaps studies might prove the ability to perceive androstenone could correlate with degree of acuity of both vomeronasal sensitivity and relative olfactory sensitivity. Another interesting hypothesis to the variance of odor response to androstenone might be linked somehow to difference in sex histocompatibility. (Scientific evidence leads to the possibility of the differential attributes being linked to, or indicative of, histocompatibility genotype profiles, aka sex-gene type profiles.) See Vomeronasal Organ, PROP, Taste Buds, Supertasters, Truffles, Mushrooms (food), Specific Anosmia, Specific Agustia, Boar Taint.
Oxford Dictionary of Biochemistry:
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androsterone
5α-androstan-3α-ol-17-one; a metabolite of testosterone, from which it is formed in the liver via androstenedione. The latter is converted to androstanedione by 3-oxo-5α-steroid 4-dehydrogenase, EC 1.3.99.5. Androstanedione in turn is acted on by 3α-hydroxysteroid dehydrogenase, EC 1.1.1.213, forming androsterone.
| androstenedione, androstenediol, androstane | |
| anemia, anergy, aneuploid |
Saunders Veterinary Dictionary:
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androsterone
An androgenic hormone, C19H30O2, excreted in the urine. When injected intramuscularly, it counteracts the effects of castration.
Wikipedia on Answers.com:
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Androsterone
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This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (October 2009) |
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| Systematic (IUPAC) name | |
| (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 53-41-8  |
| ATC code | None |
| PubChem | CID 5879 |
| ChemSpider | 5668 |
| UNII | C24W7J5D5R |
| ChEBI | CHEBI:16032 |
| ChEMBL | CHEMBL87285 |
| Chemical data | |
| Formula | C19H30O2 |
| Mol. mass | 290.440 g/mol |
| SMILES | eMolecules & PubChem |
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Not to be confused with androstenone.
Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone and weak androgen with a potency that is approximately 1/7th that of testosterone.[1] In addition, it can be converted to dihydrotestosterone (DHT) from 17-hydroxyprogesterone, bypassing conventional intermediates such as androstenedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right.[2][3]
Androsterone's 3β-isomer is epiandrosterone.
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Contents
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History
It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to estrone.
Sources
Androsterone has been shown to naturally occur in pine pollen and is well known in many animal species.[4]
Effects
Androsterone is often advertised as influencing human behavior, but there is little data to substantiate its use as a pheromone.[citation needed]
Synthesis
Androsterone, its 3β-isomer, epiandrosterone, and its 5β-isomer, etiocholanolone, are produced in the body from 5α-reduced metabolites of dehydroepiandrosterone (DHEA), androstenediol, and androstenedione such as, in the case of androsterone, 5α-androstanediol via 17β-hydroxysteroid dehydrogenase and 5α-androstanedione via 3α-hydroxysteroid dehydrogenase.[citation needed]
See also
References
- ^ Thomas Scott (1996). Concise Encyclopedia Biology. Walter de Gruyter. p. 49. ISBN 978-3-11-010661-9. http://books.google.com/books?id=LorrYj5pkKYC&pg=PA49. Retrieved 25 May 2012.
- ^ Brian E. Henderson; Bruce A. J. Ponder; Ronald Keith Ross (13 March 2003). Hormones, Genes, and Cancer. Oxford University Press. p. 23. ISBN 978-0-19-513576-3. http://books.google.com/books?id=VzIWd4faVVQC&pg=PA23. Retrieved 25 May 2012.
- ^ Kamrath C, Hochberg Z, Hartmann MF, Remer T, Wudy SA (March 2012). "Increased activation of the alternative "backdoor" pathway in patients with 21-hydroxylase deficiency: evidence from urinary steroid hormone analysis". The Journal of Clinical Endocrinology and Metabolism 97 (3): E367–75. DOI:10.1210/jc.2011-1997. PMID 22170725. http://jcem.endojournals.org/cgi/pmidlookup?view=long&pmid=22170725.
- ^ FOLIA HISTOCHEMICA ET CYTOBIOLOGICA Vol. 43, No. 2, 2005 pp. 71-79 Mammalian sex hormones in plants Anna Janeczko and Andrzej Skoczowski Institute of Plant Physiology, Polish Academy of Sciences, Kraków, Poland
External links
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Copyrights:
American Heritage Dictionary
The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.
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Wiley Dictionary of Flavors
Copyright © 2008 by Wiley-Blackwell. Wiley and the Wiley logo are registered trademarks of John Wiley & Sons, Inc. and/or its affiliates in the United States and other countries. Used here by license. Read more
Oxford Dictionary of Biochemistry
Oxford University Press. Oxford Dictionary of Biochemistry and Molecular Biology © 1997, 2000, 2006 All rights reserved.
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Saunders Veterinary Dictionary
Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.
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Mentioned in
Leopold Ružička
(Croatian–Swiss chemist)
Adolf Friedrich Johann Butenandt
(German organic chemist and biochemist)
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