Терпінеол
Lilac petals crushed between resinous fingers. Alpha-terpineol smells like the clean inside of a freshly sawn pine board dusted with spring flowers — the molecule responsible for the scent most people call 'pine-fresh,' though the floral side dominates on skin.
- Type
- Складник
- Olfactive family
- Квіткові
- Source
- Synthesized industrially from turpentine-derived alpha-pinene via terpin hydrate. Occurs naturally in over 150 essential oils including tea tree (1.5-8%), cajuput, pine, petitgrain bigarade, and neroli, but natural isolation is not commercially viable.
- Chemical class
- monoterpene alcohol
Запах
Докладно
Цікавий факт
Terpin hydrate — made by hydrating alpha-pinene through the same intermediate that yields alpha-terpineol — was one of America's most popular cough syrups for over a century, often combined with codeine. The FDA pulled it from pharmacy shelves in the early 1990s for lack of efficacy evidence. The molecule you smell in floor cleaner was once prescribed medicine.
Отримання й хімія
Спосіб отримання
Commercial alpha-terpineol is synthesized in two steps from turpentine-derived alpha-pinene: (1) acid-catalyzed hydration of alpha-pinene with ~30% sulfuric acid yields crystalline cis-terpin hydrate (mp 117°C); (2) partial dehydration of terpin hydrate produces a mixture of alpha-, beta-, and gamma-terpineol in approximately 7:2:2 ratio. The alpha isomer is isolated by fractional distillation or crystallization (mp 40-41°C). Modern one-step routes using tartaric acid/boric acid composites or solid acid catalysts achieve 96% pinene conversion at 60°C. Natural isolation from essential oils (cajuput, pine, petitgrain) is not economical. Global production is tied to turpentine supply, primarily from China, the United States, and India.
- Формула
- C10H18O
- CAS
- 98-55-5
- Ботанічна назва
- Occurs naturally in Melaleuca alternifolia (tea tree), Elettaria cardamomum (cardamom), Citrus spp.
- Зовнішній вигляд
- Colorless viscous liquid to white crystalline solid (mp 40-41°C)
- Сила запаху
- Середня
- Стійкість
- 20 hours at 100%
- Синоніми
- ALPHA-TERPINEOL BETA-TERPINEOL TERPINENE ALCOHOL
Not restricted under IFRA Amendment 51. However, classified as an EU fragrance allergen under Regulation 2023/1545 (Annex III). Mandatory label declaration required above 0.001% in leave-on products and 0.01% in rinse-off products. Compliance deadline: July 31, 2026 (new products), July 31, 2028 (existing products). TGSC max skin level in fine fragrance: 5.7%. FDA GRAS (FEMA 3045).
- Температура кипіння
- 214.00 to 218.00 °C @ 760.00 mm Hg
- Температура плавлення
- 40.00 to 41.00 °C @ 760.00 mm Hg
- Температура спалаху
- 191.00 °F TCC (88.33 °C)
- Відносна густина
- 0.93000 to 0.93600 @ 25.00 °C
- Показник заломлення
- 1.47400 to 1.48600 @ 20.00 °C
У парфумерії
Alpha-terpineol (CAS 98-55-5) is a monoterpene alcohol that functions as a floral modifier and terpenic bridge. Its dual character — lilac-floral at low concentration, pine-terpenic at high — determines its placement in a formula. Below 2%, it lifts floral compositions with a dewy, soapy-clean transparency: lilac, muguet, and freesia accords depend on it. Above 5%, the piney quality takes over and the molecule reads as a cleaning product. Recommended maximum in the fragrance concentrate: 5.7% (TGSC). In fougère structures, alpha-terpineol provides the terpenic link between lavender top notes and coumarin-mossy base. Combined with linalool and linalyl acetate, it generates the classical 'clean aromatic' masculine signature. It also bridges green-citrus top notes into woody hearts. Compatible with dihydromyrcenol for fresh-aromatic effects, with hydroxycitronellal for muguet accords, and with terpinyl acetate (CAS 80-26-2) for enhanced lilac. It is unstable in alkaline bases — in soap formulations, its scent becomes imperceptible. Classified as a EU allergen under Regulation 2023/1545 (Annex III): mandatory labeling above 0.001% in leave-on products, 0.01% in rinse-off (effective July 2026 for new products).
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