Bourgeonal
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| Surname | Bourgeonal | |||||||||||||||
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| Molecular formula | C 13 H 18 O | |||||||||||||||
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| Molar mass | 190.28 g mol −1 | |||||||||||||||
| Physical state |
liquid |
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| density |
0.9615 g cm −3 |
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| boiling point |
112-114 ° C (333 Pa) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Bourgeonal is an aromatic aldehyde used in perfume making.
Extraction and presentation
An early synthesis is based on tert- butylbenzene , which is alkylated with acrolein in the presence of boron trifluoride etherate and titanium tetrachloride .
properties
Bourgeonal is a light yellow liquid at room temperature. Its smell is reminiscent of lily of the valley and is also described as floral, watery, green and aldehydic. Bourgeonal is toxic if swallowed and may cause irritation and sensitization on skin contact .
Biological importance
2003 showed an in vitro study that one of the human cell membrane in the spermatozoa occurring olfactory receptors - the receptor hOR17-4 (or OR1D2) - among others on bourgeonal responsive. About this type of receptor particular can via a signaling cascade calcium - ion channels of sperm ( CatSper channels) are opened, which then swim twice as fast. It was therefore assumed that Bourgeonal played a role in sperm chemotaxis and was involved as a kind of attractant in guiding a sperm to the egg cell .
Later studies of the human odor threshold for various fragrances showed in 2010 that on average men perceive bourgeonal more sensitively than women. With the hypothesis that male individuals would have a selective advantage if they expressed more OR1D2 receptors - both in the sperm and in the olfactory mucosa - this was understood as confirmation of the sperm-attractive effect of Bourgeonal. A "lily of the valley phenomenon" has also been spoken of against a similar background.
However, studies from 2012 suggest that in addition to bourgeonal, various other substances can increase the mobility of sperm; this applies in particular to progesterone , which actually occurs in an effective amount in vaginal secretions. Progesterone, however, its effect can unfold without mediation of an olfactory receptor by the specific right CatSper - ion channel activated.
safety instructions
In 2015, Bourgeonal was included by the EU in the Community's rolling action plan ( CoRAP ) in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The inclusion of Bourgeonal was caused by concerns about consumer use , worker exposure and widespread use, as well as the potential risk of reproductive toxicity . The re-evaluation should be carried out by Sweden from 2020 .
Individual evidence
- ↑ Patent US2976321 : Para-tertiary-butylhydrocinnamic aldehyde. Filed on Aug. 21, 1959 , Applicant: The Givaudan Corp ..
- ↑ a b Igor Scriabine: No. 185 - Nouveau procédé de preparation des aldéhydes dihydrocinnamiques . In: Bulletin de la Société chimique de France . 1961, ISSN 0037-8968 , p. 1194-1198 .
- ↑ Entry on 3- (4-tert-butylphenyl) propionaldehyde in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
- ^ A b Marc Spehr, G. Gisselmann, A. Poplawski, JA Riffell, CH Wetzel, RK Zimmer, H. Hatt: Identification of a Testicular Odorant Receptor Mediating Human Sperm Chemotaxis . In: Science . 299, No. 5615, 2003, p. 2054. doi : 10.1126 / science.1080376 . PMID 12663925 .
- ↑ Wolfgang Legrum: Fragrances, between stink and fragrance , Vieweg + Teubner, 2011, ISBN 978-3-8348-1245-2 , p. 43.
- ^ A b Peter Olsson, Matthias Laska: Human Male Superiority in Olfactory Sensitivity to the Sperm Attractant Odorant Bourgeonal . In: Chemical Senses . 35, No. 5, 2010, pp. 427-432. doi : 10.1093 / chemse / bjq030 . PMID 20378596 .
- ↑ Hanns Hatt, Regine Dee: The lily of the valley phenomenon. Everything about smelling and how it determines our lives. Piper, Munich et al. 2008, ISBN 978-3-492-05224-5 .
- ↑ Max Planck Society: The end of the “lily of the valley phenomenon” in sperm research? February 24, 2012.
- ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 3- (4-tert-butylphenyl) propion aldehyde , accessed on March 26, 2019.