Extracting complements and substitutes from sales data: a network perspective

The complementarity and substitutability between products are essential concepts in retail and marketing. Qualitatively, two products are said to be substitutable if a customer can replace one product by the other, while they are complementary if they tend to be bought together. In this article, we take a network perspective to help automatically identify complements and substitutes from sales transaction data. Starting from a bipartite product-purchase network representation, with both transaction nodes and product nodes, we develop appropriate null models to infer significant relations, either complements or substitutes, between products, and design measures based on random walks to quantify their importance. The resulting unipartite networks between products are then analysed with community detection methods, in order to find groups of similar products for the different types of relationships. The results are validated by combining observations from a real-world basket dataset with the existing product hierarchy, as well as a large-scale flavour compound and recipe dataset.

Scalable Preparation of Enantioenriched (S)-5-methylhept-2-en-4-one. Synthesis and Aroma Properties of Achiral Analogues Thereof

(S)-5-Methylhept-2-en-4-one is a key flavour compound in hazelnuts. We have performed its chiral-pool-based chemoenzymatic synthesis with 39% overall yield (73% ee). The four-step aldol-based sequence avoids the use of highly reactive and/or toxic reagents, does not require anhydrous conditions and uses only distillation as the purification method. Thus, such methodology represents a green and scalable alternative to only two stereoselective approaches towards this natural product known so far. In addition, we have designed and prepared a set of new (di)enones as achiral synthetic analogues of the title compound. The results of their sensory analyses clearly show that relatively minor structural changes of the natural molecule significantly alter its olfactory properties. Thus, simple (poly)methylation completely changes the original hazelnut aroma of (S)-5-methylhept-2-en-4-one and shifts the odour of its analogues to eucalyptus, menthol, camphor, and sweet aroma.