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Writer's pictureArchana Shandilya

Fundamentals of LACTONE

Lactone: One of the most versatile ingredients of perfumery. Without Lactone, no one can imagine Tropical Fruit viz. (Peach, Apricot, Mango, Pineapple, Coconut) Floral (Jasmine, Gardenia, Honeysuckle, Tuberose), Vanilla, Chocolate, Nutty, Tonka character. Even some beautiful best seller fragrances also have lactone in it.



Aldehyde C-14 (So-called aldehyde) made its debut in 1919 in Guerlain Mitsouko



Apart from directly exhibiting their effect on perfume, at low dose it is helpful in giving smoother, heavier, rounded, fines note to the fragrance.


Lactone is soft but heavy and heady

The name Lactone derived from lactic acid and lactic acid in turn derives from original isolation from soured milk (Latin: Lac, Lactis)


Lactone is cyclic ester which is formed by intramolecular esterification of the corresponding Hydroxycarboxalic acid.


Lactone can have 3 cycles to 7 cycle ring, but thermodynamically and because of angle strain it is really hard to get a stable form of 3 cycles, 4 cycles, and 7 Cycle ring.



3 cycle ring also called as alpha lactone, 4 cycle ring is called as Beta lactone, 5 cycle ring is called as gamma lactone and 6 cycle ring is called as delta lactone.


Representation of symbol:

Alpha: α Beta: β Gamma: γ Delta: δ



So next time Gamma Undecalactone can also be written as γ-Undecalactone


Note - γ-Undecalactone was given trade name ‘Aldehyde c-14’ at that time, perfumers were just discovering the unusual features, strength, and power of fatty aldehyde, so any ‘aldehyde with number’ were very much in demand. Similarly γ-nonalactone becomes famous as Aldehyde C-18



Lactones are also named according to the precursor acid molecule -

  1. Aceto - 2 carbon atom

  2. Propio - 3 carbon Atom

  3. Butyro - 4 Carbon atom

  4. Valero - 5 carbon atom

  5. Capro - 6 carbon atom


So α-lactone also known as α-acetolactone, β lactone also known as β-propiolactone, γ-Lactone known as γ-Butyrolactone and δ-Lactone known as δ-valerolactone.


In Perfumery gamma and delta lactones are used remarkably like Gamma Decalactone, Gamma Dodecalactone, Gamma Octalactone, Gamma Heptalactone, Gamma Hexalactone, Delta Decalactone, Delta dodecalactone, Gamma Nonalactone, etc

Note: Other suffix used to denote lactone is – olide

Really?? Yes, some musks are actually lactones.


The majority of natural plant-derived musk are Macrocyclic lactone: Exaltolide, Ambrettolide, Ethylene Brasslate, Habanolide, Nirvanolide, Musk R1 and certain other.


Exaltolide

Lactones are given name aldehyde (so-called) just to gain market, same happened with other chemical which are actually not lactone but names are given something similar to lactone.

Eg. Maple lactone, other polycyclic musk-like Galaxolide, Cyclopentadecanolide, Tonalide, Milk lactone, etc.

Milk lactone chemical name is 5(6)-decenoic acid is an actually unsaturated carboxylic acid. It has a Waxy, creamy, buttery, lactone character.



Maple lactone or methyl cyclopentenolone (MCP) is solid crystals which smell exact Maple syrup and honey is chemically not lactone but a Ketone.

Maple Lactone


 

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Archana Shandilya

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