Phytochemistry Lecture 4: Oxygenated Compounds

<p>Both have esters that occur with them. (D)</p> Signup and view all the answers

<p>Rose-like odor (D)</p> Signup and view all the answers

<p>In the flavor industry (B)</p> Signup and view all the answers

<p>l-menthol (B)</p> Signup and view all the answers

<p>75 - 90 % (A)</p> Signup and view all the answers

<p>Cooling and filtration (B)</p> Signup and view all the answers

<p>Three (B)</p> Signup and view all the answers

<p>Thymol (D)</p> Signup and view all the answers

<p>Cooling (B)</p> Signup and view all the answers

<p>Catalytic reduction (B)</p> Signup and view all the answers

<p>RCH2OH (C)</p> Signup and view all the answers

<p>Aliphatic, Alicyclic, and Aromatic (A)</p> Signup and view all the answers

<p>Menthol (D)</p> Signup and view all the answers

<p>Primary sesquiterpenoid alcohol (D)</p> Signup and view all the answers

<p>Citronellol (D)</p> Signup and view all the answers

<p>Benzyl alcohol (D)</p> Signup and view all the answers

<p>Fractional distillation (D)</p> Signup and view all the answers

<p>Alcohols can be classified both by type of alcoholic group and carbon skeleton. (C)</p> Signup and view all the answers

<p>Tertiary alcohols (A)</p> Signup and view all the answers

<p>To separate different types of alcohols (A)</p> Signup and view all the answers

<p>Formation of crystalline derivatives (D)</p> Signup and view all the answers

<p>All of the above (D)</p> Signup and view all the answers

<p>Boiling point (A)</p> Signup and view all the answers

<p>Addition (A)</p> Signup and view all the answers

<p>They react to form unsaturated hydrocarbons (C)</p> Signup and view all the answers

<p>Primary alcohols require less drastic conditions than secondary alcohols (D)</p> Signup and view all the answers

<p>Local anesthetic (B)</p> Signup and view all the answers

<p>d-Borneol (A)</p> Signup and view all the answers

<p>Bornyl acetate (B)</p> Signup and view all the answers

<p>An artifact during the preparation of borneol-rich oils (B)</p> Signup and view all the answers

<p>Fractional distillation after saponification (B)</p> Signup and view all the answers

<p>Reduction (B)</p> Signup and view all the answers

<p>Floral (D)</p> Signup and view all the answers

<p>Cooling sensation (C)</p> Signup and view all the answers

<p>They are rapidly dehydrated. (A)</p> Signup and view all the answers

<p>Extracted with NaHCO3. (C)</p> Signup and view all the answers

<p>Primary alcohols. (D)</p> Signup and view all the answers

<p>Carbamates or urethanes. (A)</p> Signup and view all the answers

<p>Saponification. (C)</p> Signup and view all the answers

<p>Their differing melting points. (D)</p> Signup and view all the answers

<p>They can form higher temperatures around 120-130°C. (C)</p> Signup and view all the answers

<p>Through saponification with alcoholic alkalis. (D)</p> Signup and view all the answers

Alcohols commonly found in essential oils, often alongside their ester counterparts. These alcohols are typically terpenoid or aromatic in nature.

Alcohols are categorized based on the number of carbon atoms bonded to the hydroxyl group (primary, secondary, tertiary) and the structure of the carbon skeleton (aliphatic, alicyclic, aromatic).

Alcohols with a straight or branched alkane carbon skeleton; They can be saturated (single bonds) or unsaturated (double or triple bonds).

Alcohols with a cyclic carbon skeleton. Often part of terpenoid structures.

Alcohols with an aromatic ring structure, typically a benzene ring.

An alcohol where the carbon atom bearing the hydroxyl group is bonded to only one other carbon atom.

An alcohol where the carbon atom bearing the hydroxyl group is bonded to three other carbon atoms.

Essential oils containing alcohols can be separated using fractional distillation.

A monoterpenoid alcohol, a type of organic compound found in essential oils. It has a specific chemical structure and properties.

A monoterpenoid, typically obtained from citrus peels, acting as a key component in some essential oils.

A monoterpenoid obtained using cold dilute sulfuric acid as a catalyst. It is organic compound having a specific chemical structure and distinct characteristic.

A monoterpenoid alcohol, a naturally occurring compound with a lavender-like fragrance. Used widely in perfumes.

A monocyclic monoterpenoid alcohol, often isolated from mint oils. It is well-known for its cooling sensation.

A plant species containing menthol, often used for isolating menthol.

A type of mint, a source of menthol. A common plant species known for producing high amounts of menthol.

A class of organic compounds derived from isoprene units, frequently found in essential oils, with diverse uses.

A technique used to separate volatile components with high boiling points, achieved by applying reduced pressure to lower the boiling point.

Methods (CC, HPLC, GLC, etc.) used to separate chemical mixtures based on differential partitioning between stationary and mobile phases.

A technique that separates components in a mixture based on their different partition coefficients (solubility) in two immiscible solvents.

Chemical modifications turning molecules into compounds with distinct, sharp melting points enabling easier identification and quantification.

Removing water molecules from alcohols, to create unsaturated hydrocarbons. Easiest with tertiary alcohols.

Using anhydrous calcium chloride to obtain crystalline derivatives from certain primary alcohols, often in ether/benzene solutions.

Reaction of alcohols with acids to form esters; Reaction rate varies between primary, secondary, and tertiary alcohols.

Specific ester derivatives used to distinguish and quantify different types of alcohols (primary, secondary, and tertiary) based on their reactivity.

An acyclic monoterpenoid alcohol, usually found in oils of geranium, rose, and citronella. It's an optically active liquid with a rose-like odor.

An optically inactive acyclic monoterpenoid alcohol found in geranium oils. Isomers include both E and Z forms.

An optically inactive acyclic monoterpenoid alcohol, often occurring with geraniol, found in neroli oils as well. It also has isomers in both E and Z forms.

Different molecular structures having the same chemical formula. The key difference in the E/Z form is how the groups connected to the double bond are positioned about it.

A class of alcohols derived from isoprene units. Often a source component in natural essential oils, like citronella, geranium and rose scents

Products formed when phthalic anhydride reacts with alcohols, typically used for identifying alcohols through extraction.

Reaction of acid phthalates with alkaline solutions to regenerate alcohols.

Alcohols where the carbon atom with the hydroxyl group is attached to only one other carbon atom.

Alcohols where the carbon bearing the hydroxyl group is bonded to two other carbon atoms.

Alcohols where the carbon bearing the hydroxyl group is bonded to three other carbon atoms.

Esters of carbamic acid, formed with primary and secondary alcohols, used in identification.

Process using acid phthalates to isolate and purify primary and secondary alcohols.

A derivative formed from specific alcohols (like Geraniol and Nerol) that helps to identify and differentiate them.

Menthol is a monocyclic monoterpenoid alcohol, occurring as needle crystals with a strong peppermint-like odor and cooling taste.

Menthol crystals in concentrated sulfuric acid react with vanillin/sulfuric acid to produce an orange-yellow color. Adding water turns the color violet.

Borneol, a bicyclic monoterpenoid alcohol, exists as d- or l- isomers and is found in various plant oils, notably Dryobalanops camphora & D.oblongifolia for the d- isomer.

Borneol can be isolated by saponifying distilled pine needle oil, then separating through fractional distillation and crystallization.

-Terpineol is a key ingredient in the synthesis of various hydrocarbons and oxygenated monoterpenoids.

Isoborneol is a byproduct of borneol extraction. It is not found naturally and is unstable under strong dehydrating agents.

Borneol can be created from -pinene or through modification of camphor via chemical reduction.

Monoterpenoid alcohols like menthol, borneol, and terpineol are crucial components in essential oils with various applications like flavoring, fragrances, and medicinal uses.