Bourgeonal

Last updated
Bourgeonal
Bourgeonal.svg
Bourgeonal 3D BS.png
Names
Preferred IUPAC name
3-(4-tert-Butylphenyl)propanal
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.038.182 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 242-016-2
PubChem CID
UNII
  • 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
  • O=CCCc1ccc(cc1)C(C)(C)C
Properties
C13H18O
Molar mass 190.286 g·mol−1
AppearancePale 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).

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.

Contents

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.

Related Research Articles

<span class="mw-page-title-main">Pheromone</span> Secreted or excreted chemical factor that triggers a social response in members of the same species

A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavior of the receiving individuals. There are alarm pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology. Pheromones are used by many organisms, from basic unicellular prokaryotes to complex multicellular eukaryotes. Their use among insects has been particularly well documented. In addition, some vertebrates, plants and ciliates communicate by using pheromones. The ecological functions and evolution of pheromones are a major topic of research in the field of chemical ecology.

<span class="mw-page-title-main">Olfactory receptor</span> Chemoreceptors expressed in cell membranes of olfactory receptor neurons

Olfactory receptors (ORs), also known as odorant receptors, are chemoreceptors expressed in the cell membranes of olfactory receptor neurons and are responsible for the detection of odorants which give rise to the sense of smell. Activated olfactory receptors trigger nerve impulses which transmit information about odor to the brain. In vertebrates, these receptors are members of the class A rhodopsin-like family of G protein-coupled receptors (GPCRs). The olfactory receptors form the largest multigene family in vertebrates consisting of around 400 genes in humans and 1400 genes in mice. In insects, olfactory receptors are members of an unrelated group of ligand-gated ion channels.

<span class="mw-page-title-main">Aroma compound</span> Chemical compound that has a smell or odor

An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently volatile for transmission via the air to the olfactory system in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds, particularly strawberries which are commercially cultivated to have appealing aromas, and contain several hundred aroma compounds.

<span class="mw-page-title-main">Docking theory of olfaction</span> Scientific theory about scent perception

The docking theory of olfaction proposes that the smell of an odorant molecule is due to a range of weak non-covalent interactions between the odorant [a ligand] and one or more G protein-coupled odorant receptors. These include intermolecular forces, such as dipole-dipole and Van der Waals interactions, as well as hydrogen bonding. More specific proposed interactions include metal-ion, ion-ion, cation-pi and pi-stacking. Interactions can be influenced by the hydrophobic effect. Conformational changes can also have a significant impact on interactions with receptors, as ligands have been shown to interact with ligands without being in their conformation of lowest energy.

The vibration theory of smell proposes that a molecule's smell character is due to its vibrational frequency in the infrared range. This controversial theory is an alternative to the more widely accepted docking theory of olfaction, which proposes that a molecule's smell character is due to a range of weak non-covalent interactions between its protein odorant receptor, such as electrostatic and Van der Waals interactions as well as H-bonding, dipole attraction, pi-stacking, metal ion, Cation–pi interaction, and hydrophobic effects, in addition to the molecule's conformation.

The odor detection threshold is the lowest concentration of a certain odor compound that is perceivable by the human sense of smell. The threshold of a chemical compound is determined in part by its shape, polarity, partial charges, and molecular mass. The olfactory mechanisms responsible for a compound's different detection threshold is not well understood. As such, odor thresholds cannot be accurately predicted. Rather, they must be measured through extensive tests using human subjects in laboratory settings.

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<span class="mw-page-title-main">OR1D2</span> Protein-coding gene in the species Homo sapiens

Olfactory receptor 1D2 is a protein that in humans is encoded by the OR1D2 gene.

<span class="mw-page-title-main">OR2W1</span> Protein-coding gene in the species Homo sapiens

Olfactory receptor 2W1 is a protein that in humans is encoded by the OR2W1 gene.

<span class="mw-page-title-main">OR51B2</span> Protein-coding gene in the species Homo sapiens

Olfactory receptor 51B2 is a protein that in humans is encoded by the OR51B2 gene.

<span class="mw-page-title-main">OR51L1</span> Protein-coding gene in the species Homo sapiens

Olfactory receptor 51L1 is a protein that in humans is encoded by the OR51L1 gene.

<span class="mw-page-title-main">OR2T11</span> Protein-coding gene in the species Homo sapiens

Olfactory receptor 2T11 is a protein that in humans is encoded by the OR2T11 gene.

<span class="mw-page-title-main">OR2T4</span> Protein-coding gene in the species Homo sapiens

Olfactory receptor 2T4 is a protein that in humans is encoded by the OR2T4 gene.

<span class="mw-page-title-main">OR51E1</span> Protein-coding gene in the species Homo sapiens

Olfactory receptor 51E1 is a protein that in humans is encoded by the OR51E1 gene.

<span class="mw-page-title-main">OR13H1</span> Protein-coding gene in the species Homo sapiens

Olfactory receptor 13H1 is a protein that in humans is encoded by the OR13H1 gene.

<span class="mw-page-title-main">OR10G4</span> Protein-coding gene in the species Homo sapiens

Olfactory receptor 10G4 is a protein that in humans is encoded by the OR10G4 gene.

<span class="mw-page-title-main">OR2J3</span> Protein-coding gene in the species Homo sapiens

Olfactory receptor 2J3 is a protein that in humans is encoded by the OR2J3 gene.

<span class="mw-page-title-main">Odor</span> Volatile chemical compounds perceived by the sense of smell

An odor or odour is a smell or a scent caused by one or more volatilized chemical compounds generally found in low concentrations that humans and many animals can perceive via their olfactory system. While smell can refer to pleasant and unpleasant odors, the terms scent, aroma, and fragrance are usually reserved for pleasant-smelling odors and are frequently used in the food and cosmetic industry to describe floral scents or to refer to perfumes.

<span class="mw-page-title-main">Sense of smell</span> Sense that detects smells

The sense of smell, or olfaction, is the special sense through which smells are perceived. The sense of smell has many functions, including detecting desirable foods, hazards, and pheromones, and plays a role in taste.

<span class="mw-page-title-main">Mammalian reproduction</span> Most mammals are viviparous, giving birth to live young

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References

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