Terpineol

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alpha-Terpineol
Skeletal formula
Names
IUPAC name
2-(4-Methyl-1-cyclohex-3-enyl)propan-2-ol
Other names
alpha-Terpineol
α-Terpineol
p-Menth-1-en-8-ol
α,α,4-Trimethylcyclohex-3-ene-1-methanol
Terpene alcohol
Identifiers
98-55-5 YesY
ChEBI CHEBI:22469 YesY
ChEMBL ChEMBL507795 N
ChemSpider 13850142 YesY
Jmol 3D model Interactive image
UNII 21334LVV8W YesY
  • InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3 YesY
    Key: WUOACPNHFRMFPN-UHFFFAOYSA-N YesY
  • InChI=1/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
    Key: WUOACPNHFRMFPN-UHFFFAOYAL
  • C\C1=C\CC(CC1)C(O)(C)C
Properties
C10H18O
Molar mass 154.25 g·mol−1
Appearance Colorless liquid[1]
Density 0.93 g/cm3[1]
Melting point −35.9 to −28.2 °C (−32.6 to −18.8 °F; 237.2 to 245.0 K)[1] (mixture of isomers)
Boiling point 214–217 °C (417–423 °F; 487–490 K)[1] (mixture of isomers)
2.42 g/L[1]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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.[2] 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.

File:Terpineols.png
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.[3] (+)-α-Terpineol is a chemical constituent of scullcap.

Synthesis

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:[4]

File:Terpineolsynthesisfromlimonene.png
Terpineol synthesisfrom limonene

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

References

  1. 1.0 1.1 1.2 1.3 1.4 Record in the GESTIS Substance Database of the IFA
  2. Merck Index, 11th Edition, 9103
  3. Lua error in package.lua at line 80: module 'strict' not found.
  4. Lua error in package.lua at line 80: module 'strict' not found.

External links

  • MSDS for alpha-terpineol
  • Media related to Lua error in package.lua at line 80: module 'strict' not found. at Wikimedia Commons

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