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Patchoulol

Patchoulol is a science topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Patchoulol rather than just read about it. In short: Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in patchouli (Pogostemon cablin). Patchouli oil is an important material in perfumery.

Patchoulol — main illustration
Patchoulol — illustration

Key takeaways

  • Patchoulol belongs to science; place it in that map before memorising details.
  • Learn the definition first, then one example that makes the definition concrete.
  • Connect Patchoulol to a quantity you can measure, compute or draw — that is where exam questions come from.
  • Reproduce the core statement of Patchoulol from memory before moving on to harder problems.

Reference excerpt

Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in patchouli (Pogostemon cablin). Patchouli oil is an important material in perfumery. The (−)-optical isomer is one of the organic compounds responsible for the typical patchouli scent. Patchoulol is obtained industrially from patchouli leaf fermentation. Patchoulol is also used in the synthesis of the chemotherapy drug Taxol.

Structure determination Gal first isolated patchouli alcohol in 1869, and Montgolfier later formulated its chemical composition (correctly) as C15H26O. Early structural investigation soon established the presence of a saturated tricyclic tertiary alcohol. After several years of careful degradation study, Büchi and co-workers proposed in 1961 that patchouli alcohol had the structure 1. A subsequent synthesis of material which corresponded to an authentic sample of natural patchouli alcohol appeared to verify Büchi's proposal.

However, Dunitz and co-workers serendipitously discovered in 1963 that Büchi's structure is in fact incorrect. Dunitz et al. had undertaken X-ray analysis of the patchouli alcohol diester with chromic acid, intending to determine the Cr-O-C angles. In the course of their analysis they could not reconcile the X-ray evidence with the "known" structure 1. In a joint paper with Büchi, they collectively proposed that patchouli alcohol in fact had the novel structure 2. The discrepancy had resulted from an unanticipated skeletal rearrangement when patchoulene was treated with peroxy acid in Büchi's confirmatory synthesis. The rearranged molecule coincidentally exhibited the correct natural product architecture.

See also Norpatchoulenol

References

External links Chime 3D representation

Illustrations

Patchoulol illustration
Patchoulol illustration
Patchoulol: Proposed sequence for the synthesis of patchouli alcohol.
Proposed sequence for the synthesis of patchouli alcohol.
Patchoulol: Actual sequence for the synthesis of patchouli alcohol.  Contains embedded bicyclo[2.2.2]octane motif.
Actual sequence for the synthesis of patchouli alcohol. Contains embedded bicyclo[2.2.2]octane motif.

Worked examples

Example 1 — a first encounter with Patchoulol

Start with the simplest possible case. Write down what Patchoulol claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In science, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Patchoulol before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Patchoulol ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Patchoulol

In research
Patchoulol appears in science research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry
Engineering practice reuses Patchoulol in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom
Patchoulol is common in secondary-school and first-year university syllabi. It links to neighbouring topics Perfume ingredients, Sesquiterpenes, Tertiary alcohols, so understanding it makes those chapters shorter.
In everyday life
Look for Patchoulol outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.
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How to study Patchoulol in 20 minutes

  1. Read the reference excerpt below once, without taking notes.
  2. Close the page and write down what Patchoulol means in your own words.
  3. Compare your version with the excerpt and mark what you missed.
  4. Work through the three examples above with pen and paper.
  5. Explain Patchoulol out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Patchoulol in simple terms?

Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in patchouli (Pogostemon cablin). Patchouli oil is an important material in perfumery.

Why does Patchoulol matter?

Because it connects several science ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Patchoulol?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Patchoulol.

Tags

  • Perfume ingredients
  • Sesquiterpenes
  • Tertiary alcohols

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