Bourgeonal

Bourgeonal
Names
	Preferred IUPAC name 3-(4-tert-Butylphenyl)propanal
Identifiers
CAS Number	18127-01-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	58364;
ECHA InfoCard	100.038.182
EC Number	242-016-2;
PubChem CID	64832;
UNII	H3XVS6E70V ;
CompTox Dashboard (EPA)	DTXSID6044808 ;
	InChI InChI=1/C13H18O/c1-13(2,3)12-8-6-11(7-9-12)5-4-10-14/h6-10H,4-5H2,1-3H3 Key: FZJUFJKVIYFBSY-UHFFFAOYAX;
	SMILES O=CCCc1ccc(cc1)C(C)(C)C;
Properties
Chemical formula	C13H18O
Molar mass	190.286 g·mol−1
Appearance	Pale yellow liquid
Density	0.938 g/cm3
Boiling point	265.1 °C (509.2 °F; 538.2 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Bourgeonal is an aromatic aldehyde used in perfumery. It has a fragrance reminiscent of lily of the valley, otherwise described as floral, watery, green, and aldehydic. It is a pale yellow liquid at room temperature.

Synthesis

Industrial synthesis of bourgeonal involves a mixed aldol reaction of 4-tert-butylbenzaldehyde and acetaldehyde, followed by hydrogenation. Alternatively it may be produced by the alkylation of tert-butylbenzene with propanal (often in its acetal form).^[1]

Biological effects

In a 2003 study it was found that in vitro, bourgeonal acts as a chemo-attractant for human spermatozoa, activating an olfactory receptor called OR1D2 (formerly called hOR17-4)^[2] which opens calcium ion channels in the sperm, leading them to swim twice as fast.^[3] Bourgeonal is suspected to be involved in helping sperm locate the ovum.

As of 2010, bourgeonal is the only known odor substance to which males have a higher average sensitivity than females.^[2] This is thought to be because the same olfactory receptor (OR1D2) is expressed in non-olfactory tissue in sperm cells as well as the olfactory tissue of the nose. The involvement with sperm chemotaxis causes an evolutionary pressure for males (sexual selection) that causes them to have more OR1D2 receptors on average, both in the nose as well as in sperm.

References

^ Ramachanderan, Raghavendra; Schaefer, Bernd (June 2019). "Lily-of-the-valley fragrances". ChemTexts. 5 (2). doi:10.1007/s40828-019-0081-8.
^ ^a ^b Peter Olsson and Matthias Laska (2010). "Human Male Superiority in Olfactory Sensitivity to the Sperm Attractant Odorant Bourgeonal". Chemical Senses. 35 (5): 427–32. doi:10.1093/chemse/bjq030. PMID 20378596.
^ Spehr, M.; Gisselmann, G; Poplawski, A; Riffell, JA; Wetzel, CH; Zimmer, RK; Hatt, H (2003). "Identification of a Testicular Odorant Receptor Mediating Human Sperm Chemotaxis". Science. 299 (5615): 2054–58. Bibcode:2003Sci...299.2054S. doi:10.1126/science.1080376. PMID 12663925. S2CID 45306091.

[1] Ramachanderan, Raghavendra; Schaefer, Bernd (June 2019). "Lily-of-the-valley fragrances". ChemTexts. 5 (2). doi:10.1007/s40828-019-0081-8.

[olsson2010-2] Peter Olsson and Matthias Laska (2010). "Human Male Superiority in Olfactory Sensitivity to the Sperm Attractant Odorant Bourgeonal". Chemical Senses. 35 (5): 427–32. doi:10.1093/chemse/bjq030. PMID 20378596.

[3] Spehr, M.; Gisselmann, G; Poplawski, A; Riffell, JA; Wetzel, CH; Zimmer, RK; Hatt, H (2003). "Identification of a Testicular Odorant Receptor Mediating Human Sperm Chemotaxis". Science. 299 (5615): 2054–58. Bibcode:2003Sci...299.2054S. doi:10.1126/science.1080376. PMID 12663925. S2CID 45306091.

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