TERPINEOL
what is TERPINEOL?
Synthetic Ingredient For Perfumery Overview
Chemically 2-(4-Methylcyclohex-3-en-1-yl)propan-2-ol is a monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are four isomers, alpha-, beta-, gamma-terpineol, and terpinen-4-ol. Beta- and gamma-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. Alpha-Terpineol is one of the two most abundant aroma constituents of lapsang souchong tea;Terpineol, or more strictly, alpha-terpineol, is one of the most widespread of monocyclic monoterpenoid alcohols in nature. It is found in flowers such as narcissus and freesia; herbs such as sage, marjoram, oregano, and rosemary; in the leaf oil of Ti-tree (Melaleuca alternifolia) and in the oil expressed from the peel of lemons. Reports of the level of terpineol in oils occasionally vary considerably and one wonders how much this is due to variations in the plants and to variations in the isolation process since terpineol could be an artifact. The layman will often describe the odor of terpineol as “pine disinfectant” since terpineol is, in fact, a major component of pine disinfectant. This product is prepared by distillation of turpentine in the presence of an acid which results in an opening of the ring of a-pinene to produce a-terpineol. The driving force for the reaction comes from the release of the strain in the 4-membered ring in the a-pinene skeleton. The initial step in the process is the protonation of the double bond in a-pinene. This generates a carbocation center adjacent to the strained cyclobutane ring. The ring strain can be released by movement of one pair of electrons from a single bond of the cyclobutane ring towards the positive charge with the formation of a double bond. The resultant carbocation in the tail of the molecule can then be quenched by addition of water followed by loss of a proton), giving alpha-terpineol.
Profile
📂 CAS N° 98-55-5
⚖️ MW 154,25 g/mol
📝 Odor Type: Fresh (Terpenic)
📈 Odor Strength: Medium. Stays about 20hrs on a smelling strip.
👃🏼 Odor Profile: Terpineol is Fresh, clean, with a dirty undertone. It is also Floral lilac and has the linalool floralcy. It makes me think of the classics detergents that clean everything.
👅 Flavor Profile: Citrus, woody, lemon-lime, soapy.
⚗️ Uses: excellent for citrus, tropical fruits, apple, tomato, and coffee flavors. As a basic component in Lilac perfumes and a major component of many varieties of Pine fragrances (lower grades of Terpineol will usually suffice) as a common ingredient of Fougeres, Apple blossoms, fragrances for household products, soaps, detergents, etc.
Sources:
Fulvio Ciccolo
Terpenoid Chemistry (Charles Sell)
National Center for Biotechnology Information (2020). PubChem Compound Summary for CID 17100, alpha-TERPINEOL. Retrieved November 24, 2020 from https://pubchem.ncbi.nlm.nih.gov/compound/alpha-TERPINEOL.