UNDECALACTONE GAMMA
what is UNDECALACTONE GAMMA?
Synthetic Ingredient For Perfumery Overview
Undecalactone Gamma, commonly named Aldehyde C14, it is an 11 carbon chain Lactone. Its discovery dates 1908 and is attributed to Jukov Schestakow Strongly developed and exploited in two years after, (the 1910s) used in fragrance like Mitsouko. Exploited by fashion designers like Caron and Poiret. Almost colorless or very pale straw-colored, slightly viscous liquid.Practically insoluble in water, soluble in alcohol and oils, and in aqueous alkali.Sweet, oily-fruity, Peach-like taste in concentrations lower than 20 ppm. The effect at higher concentrations is not unpleasant, but strongly fruity, supporting other fruity notes, necessarily present at a high concentration of the Lactone. This material is widely used, although in minute amounts, in perfume compositions. In order of frequency in use, it ranks very high among the materials on the perfumer’s shelf. But it is not the kind of material ordinarily sold in drum-lots. However, after the success of a new perfume (type) in the 1950s, the title material had a further increase in popularity, when numerous perfumers used it at unusually high levels along with new non-Nitro musk chemicals, in order to duplicate part of the new note in the successful perfume. The author has yet to see a duplication that sells better than the original (in perfumes), but it must be admitted that Undecalactone drew benefit from this popularity.
The Name
the perfume industry stubbornly uses the name “Peach Aldehyde”, and it puzzles the chemist who knows that the material is not an aldehyde and does not have the disadvantages of an aldehyde in a composition. It is doubly amusing to notice the reports from the intense research on natural components of Peach pulp and juice. The Lactones with 6, 7, 8, 9, 10 and 12 Carbon atoms have been identified, while the Undecalactone with 11 Carbons – has not been identified with certainty. Which makes the name Peach Aldehyde somewhat unjustified.However, one should not forget that the effect of the lactone seems to please customers and this is generally what counts.
Production
Chemists can produce undecalactone gamma by Lactonization of Undecylenic acid with sulfuric acid. This process will yield minor amounts of delta-isomer.
From Octanol-1 plus Methyl acrylate, with Di-tertiary-Butylperoxide.
From heptyl ethylene oxide plus Sodiomalonic ester
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.
Perfumers used the material in Violet compositions which were popular at the time of discovery of this Lactone (about 1900). Today its most important use is in flavors. Primarily in imitation Peach, but also in many fruity types. Often as a fixative for the very volatile fruit esters.
Normal concentrations in finished products are 3 to 12 ppm, but it may be as high as 100 ppm in chewing gum. As mentioned above, the high concentrations demand considerable “construction” of heavy flavor chemicals around the lactone, otherwise, it will perform in a rather greasy-unpleasant manner. Vanillin, Palatone (Veltol), Ethyl Veltol, Sweet Orange oil, etc. may support the Lactone and make it palatable at the high concentration and at the same time take advantage of the enormous effect in aroma volume increase supplied by this Lactone.
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.