Terpineol

Terpineol
alpha-Terpineol
Identifiers
CAS number 98-55-5 YesY
ChemSpider 13850142 YesY
UNII 21334LVV8W YesY
ChEBI CHEBI:22469 N
ChEMBL CHEMBL507795 N
Jmol-3D images Image 1
Properties
Molecular formula C10H18O
Molar mass 154.25 g/mol
Density 0.9338 g/cm3
Melting point

18 °C

Boiling point

219 °C
81-82 °C at 4.5 mmHg

Hazards
MSDS External MSDS
NFPA 704
NFPA 704.svg
1
2
0
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil[1]. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent.

Terpineols: alpha-, beta-, gamma-, and the 4-terpineol isomer

Terpineol has a pleasant odor similar to lilac and is a common ingredient in perfumes, cosmetics, and flavors. α-terpineol is one of the two most abundant aroma constituents of lapsang souchong tea; the α-terpineol originates in the pine smoke used to dry the tea.[2]

Although it is naturally occurring, terpineol is commonly manufactured from the more readily available alpha-pinene.

In one study, an alternative route starting from d-limonene was demonstrated[3]:

Terpineol synthesisfrom limonene

Limonene is reacted with trifluoroacetic acid in a Markovnikov addition to a trifluoro acetate intermediate, which is easily hydrolyzed with sodium hydroxide to α-terpineol with 76% selectivity. Side-products are the β-terpineol in a mixture of cis-isomer and trans isomer and 4-terpineol.

References

  1. ^ Merck Index, 11th Edition, 9103.
  2. ^ Shan-Shan Yao; Wen-Fei Guo; YI Lu; Yuan-Xun Jiang, "Flavor Characteristics of Lapsang Souchong and Smoked Lapsang Souchong,a Special Chinese Black Tea with Pine Smoking Process", Journal of Agricultural and Food Chemistry, Vol. 53, No.22, (2005)
  3. ^ A Practical Synthesis of d--Terpineol via Markovnikov Addition of d-Limonene Using Trifluoroacetic Acid Yoshifumi Yuasa and Yoko Yuasa Org. Process Res. Dev.; 2006; 10(6) pp 1231 - 1232; (Article) doi:10.1021/op068012d

External links


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Look at other dictionaries:

  • terpinéol — ● terpinéol ou terpinol nom masculin Alcool monoterpénique obtenu par déshydratation partielle de la terpine. terpinol [tɛʀpinɔl] ou terpinéol [tɛʀpineɔl] n. m. ÉTYM. 1872, terpinole; de terpine, et suff. ol. ❖ ♦ Chim., techn. Composé tiré de la… …   Encyclopédie Universelle

  • Terpineol — Terpineol, Bestandteil mehrerer ätherischer Oele, als künstlicher Riechstoff durch Behandeln von Terpentinöl mit essigsaurem Natron und Schwefelsäure, Verseifung und Destillation gewonnen. Es bildet eine dickliche Flüssigkeit von 0,940… …   Lexikon der gesamten Technik

  • Terpineol — Terpineōl, aus Terpentinhydrat und Terpin gewonnenes farbloses Öl, findet sich in ätherischen Ölen, riecht stark nach Flieder und findet deshalb in der Parfümerie Verwendung (Fliederduft) …   Kleines Konversations-Lexikon

  • terpineol — TERPINEÓL s.n. v. terpinol. Trimis de LauraGellner, 13.09.2007. Sursa: DN …   Dicționar Român

  • terpineol — [tər pin′ē ôl΄, tər pin′ēōl΄] n. [< terpine, C10H18(OH)2 (< TERPENE + INE3) + OL1] any of three isomeric alcohols, C10H17OH, with a lilac odor, found in certain volatile oils and used in perfumes …   English World dictionary

  • Terpineol — Terpineole sind eine Gruppe chemischer Verbindungen, von denen mindestens vier (α , β , γ und δ Terpineol) als sekundäre Pflanzenstoffe natürlich vorkommen. Chemisch sind es monocyclische Monoterpen Alkohole mit der Summenformel C10H18O. Sie sind …   Deutsch Wikipedia

  • terpineol — ˌtərˈpinēˌȯl, ˌōl noun ( s) Etymology: International Scientific Vocabulary terpine, terpin + ol : any of three fragrant isomeric unsaturated low melting crystalline terpenoid alcohols C10H17OH or a viscous liquid commercial mixture containing… …   Useful english dictionary

  • Terpineol — Ter|pi|ne|ol [↑ Terpentin u. ↑ ol (1)], das; s, e: Gemisch von p Menthenolen, die oder deren Ester parfümistisch eingesetzt werden. * * * Terpineol   [zu Terpentin und vergleiche. ..ol] das, s, monozyklisch ungesättigter Terpenalkohol, von dem… …   Universal-Lexikon

  • terpineol — terpineolis statusas T sritis chemija formulė C₁₀H₁₇OH atitikmenys: angl. terpineol rus. терпинеол …   Chemijos terminų aiškinamasis žodynas

  • terpineol — noun Etymology: International Scientific Vocabulary, from terpine (C10H18(OH)2) Date: 1848 any of three fragrant isomeric alcohols C10H17OH found in essential oils or made artificially and used especially in perfume or as solvents …   New Collegiate Dictionary

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