Surf Wiki
Save to docs
general/flavors

From Surf Wiki (app.surf) — the open knowledge base

Terpineol

2-(4-Methylcyclohex-3-en-1-yl)propan-2-ol alpha-terpineol α-terpineol α,α,4-Trimethylcyclohex-3-ene-1-methanol Terpene alcohol | NFPA-H = 2 | NFPA-F = 1 | NFPA-R = 0 | NFPA-S =

Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil, pine oil, and petitgrain oil. Four isomers exist: α-terpineol, β-terpineol, γ-terpineol, and terpinen-4-ol. β-Terpineol and γ-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with α-terpineol as the major constituent.

:[[File:Terpineols.svg|left|thumb|350x350px|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. (+)-α-Terpineol is a chemical constituent of skullcap.

Synthesis and biosynthesis

Although it is naturally occurring, terpineol is commonly manufactured from alpha-pinene, which is hydrated in the presence of sulfuric acid.

An alternative route starts from limonene:

:[[Image:Terpineolsynthesisfromlimonene.png|thumb|left|400px|Terpineol synthesis from limonene]]

Limonene reacts with trifluoroacetic acid in a Markovnikov addition to a trifluoroacetate intermediate, which is easily hydrolyzed with sodium hydroxide to α-terpineol with 7% selectivity. Side-products are β-terpineol in a mixture of the cis isomer, the trans isomer, and 4-terpineol.

The biosynthesis of α-terpineol proceeds from geranyl pyrophosphate, which releases pyrophosphate to give the terpinyl cation. This carbocation is the precursor to many terpenes and terpenoids. Its hydrolysis gives terpineol. :[[File:TerpeneVterpenoid.svg|thumb|460px|left|Biosynthetic conversion of [[geranyl pyrophosphate]] to the terpenes [[Alpha-pinene|α-pinene]] and [[Beta-pinene|β-pinene]] (right) and to α-terpineol (bottom left).]]

References

References

  1. {{GESTIS
  2. {{Merck11th
  3. (2005). "Flavor Characteristics of Lapsang Souchong and Smoked Lapsang Souchong, a Special Chinese Black Tea with Pine Smoking Process". Journal of Agricultural and Food Chemistry.
  4. (June 15, 2000). "Turpentines, 16. Pine Oil".
  5. (2006). "A Practical Synthesis of ''d''-α-Terpineol via Markovnikov Addition of ''d''-Limonene Using Trifluoroacetic Acid". Organic Process Research & Development.
  6. (2000). "Biosynthesis". Topics in Current Chemistry.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

flavors monoterpenes alkenols cyclohexenes
Want to explore this topic further?

Ask Mako anything about Terpineol — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report