Sedative Effects of Inhaled Benzylacetone

Mar. 22, 2021

Benzylacetone (IUPAC name: 4-phenyl-2-butanone) is a liquid with a sweet, flowery smell that is considered to be the most abundant attractant compound in flowers (e.g. Coyote Tobacco, Nicotiana attenuata) and one of the volatile components of cocoa; It can be used as an attractant for melon flies (Bactrocera cucurbitae), in perfume, and as an odorant for soap. It can be prepared by the hydrogenation of benzylideneacetone.

4-Phenyl-2-butanone is an attractant compound found in the flower Nicotiana attenuata. It is also used in the preparation of 4-oxocyclohexanecarbaldehyde derivatives.

 

Benzylacetone has been identified as a volatile component of cocoa. Benzylacetone(CAS 2550-26-70) is a sweet-floral-smelling liquid, which can be prepared by selective hydrogenation of benzylidene acetone (from benzaldehyde and acetone). It is used in soap perfumes.

Benzylacetone

Benzylacetone is released through heated sedum and is effective in reducing spontaneous activity in mice when inhaled. The present study investigated the relationship between the sedative activity of benzylacetone and its derivatives and the chemical structure of these compounds by comparing the activity in mice treated with a range of compounds. It has been shown that benzylacetone-like compounds have sedative activity and that their strength varies depending on the functional group in the carbon chain, the substituent in the benzene ring and its combination. Quantitative conformational studies were carried out using a series of 17 benzylacetone derivatives to identify the structural features important for sedative activity.

 

Jinkoh (Sinkiang) is a resinous trunked incense species that is used in Chinese herbal formulations, as well as in traditional herbal prescriptions. It is also used in Kodo (Japanese incense rituals) because of the aroma it releases when heated. The aromatic components of incense include sesquiterpenes, chromone derivatives and low molecular weight aromatic compounds.

 

1) Benzylacetone is a low molecular weight aromatic compound that is high in the aroma of heated incense wood but is not present in the wood or oil.

2) When inhaled, the compound is a potent inhibitor of locomotor activity in mice.

3) The odour of the aroma has traditionally been associated with this sedative effect.  The study of the sedative effects of benzylacetone may provide scientific insight into the traditional Japanese culture of "listening to incense".

The relaxing effects of fragrances have been used in aromatherapy and other health activities. It has recently been reported that scenting agents can be used in therapies for anxiety or dementia.

4)As the effects and applications of these therapies have received much attention and pharmacological effects and their mechanisms of action have been studied.  However, several relationships between chemical structure and pharmacological action remain unknown.

 

Benzylacetone has a simple structure, a benzene ring, a saturated carbon chain and a functional group. However, it is assumed that only a few features are essential for the low-velocity motor action of benzylacetone. In this paper, we have investigated the relationship between the sedative activity of benzylacetone and its derivatives and the chemical structure of the compounds by comparing their activity in mice treated with a range of compounds. The compounds examined in this study are derivatives of benzylacetone in which the ketone group is substituted with other functional groups, i.e., structural isomers and derivatives with substituents on the benzene ring. Quantitative conformational relationship (QSAR) studies were carried out using a series of 17 benzylacetone derivatives to determine the structural features that are essential for sedative activity.



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