Undecalactone Gamma (Aldehyde C14)

Profile:

• 📂 CAS N° 104-67-6

• ⚖️ MW — 184.27 g/mol

• 📝 Odor Type — Fruity, with a peach specific character.

• 📈 Odour Strength — medium stays 330h on a strip.

• 👃🏼 Odor Profile — Creamy, fatty, fruity, coconut, peach, Iactonic, ketonic and fruity. I make a link with a nutty peach.

• 👅 Flavour Profile — Fatty, coconut, creamy, vanilla, nutty, macadamia and peach.Used in peach, apricot, pear, maple, coconut, tropical, butterscotch, grenadine and date flavors.

• ⚗️ Uses — it blends excellently with Nonalactone in Gardenia and Tuberose, and in many versions of Lilac bases. It extends the depth of an Orangeblossom often too harsh with conventional materials, and it is a frequent component of Honeysuckle, etc..Concentrations far below 1 are effective, and it is at times possible to ruin a fragrance with 0.1 or 0,2  of the title material, just as well as it is possible to double the floral sweetness and depth of another fragrance with that amount of Undecalactone.

Undecalactone Gamma, commonly known as Aldehyde C14, is an 11-carbon chain lactone. Its discovery dates back to 1908 and is attributed to Jukov Schestakow. Strongly developed and exploited in the early 1910s, it was used in fragrances like Mitsouko and by fashion designers such as Caron and Poiret.

Characteristics

Undecalactone Gamma is an almost colorless or very pale straw-colored, slightly viscous liquid. It is practically insoluble in water but soluble in alcohol, oils, and aqueous alkali. It has a sweet, oily-fruity, peach-like taste in concentrations lower than 20 ppm. At higher concentrations, it remains strongly fruity, supporting other fruity notes and is necessarily present at a high concentration of the lactone.

Usage in Perfumery

This material is widely used in perfume compositions, albeit in minute amounts. It ranks very high among the materials on a perfumer’s shelf but is not typically sold in drum-lots. In the 1950s, after the success of a new perfume type, Undecalactone Gamma gained further popularity. Numerous perfumers used it at unusually high levels along with new non-nitro musk chemicals to replicate part of the new note in the successful perfume. Despite its widespread use, no duplication has sold better than the original, although Undecalactone Gamma benefited from this increased popularity.

The Name Controversy

The perfume industry often uses the name “Peach Aldehyde,” puzzling chemists who know that the material is not an aldehyde and does not have the disadvantages of an aldehyde in a composition. It is amusing to note that intense research on natural components of peach pulp and juice has identified lactones with 6, 7, 8, 9, 10, and 12 carbon atoms, but not the undecalactone with 11 carbons. This makes the name “Peach Aldehyde” somewhat unjustified. However, the lactone’s pleasing effect on customers is what generally counts.

Production

Chemists can produce Undecalactone Gamma by lactonization of undecylenic acid with sulfuric acid, yielding minor amounts of delta-isomer. Other methods include:

• From Octanol-1 plus Methyl acrylate, with Di-tertiary-Butylperoxide.

• From Heptyl ethylene oxide plus Sodiomalonic ester.

Application in Flavors

Perfumers initially used Undecalactone Gamma in violet compositions popular around 1900. Today, its most important use is in flavors, primarily in imitation peach but also in many fruity types. It often serves as a fixative for very volatile fruit esters. Normal concentrations in finished products range from 3 to 12 ppm, but it may be as high as 100 ppm in chewing gum. High concentrations require considerable “construction” of heavy flavor chemicals around the lactone to prevent it from performing in a greasy-unpleasant manner. Vanillin, Palatone (Veltol), Ethyl Veltol, Sweet Orange oil, etc., may support the lactone, making it palatable at high concentrations while taking advantage of the significant aroma volume increase provided by this lactone.

Conclusion

Undecalactone Gamma, with its distinctive peach-like flavor and aroma, remains a staple in both the perfume and flavoring industries. Despite the controversies surrounding its name, its popularity and utility have continued to grow, cementing its place in the world of scents and tastes.

Sources:

• The chemistry of fragrance, David H Pybus and Charles S. Sell.

•  S. Arctander

• Fulvio Ciccolo

• National Center for Biotechnology Information (2020). PubChem Compound Summary for CID 7714, gamma-Undecalactone. Retrieved November 25, 2020 from https://pubchem.ncbi.nlm.nih.gov/compound/gamma-Undecalactone.