Lactones

POPULAR & WEIRDcreamy · fruity · gourmand

Seven perfumesOne of them is looking at you

HeartPyramid

—Strength

100hTenacity

—Origins

Specimen

Definition

Lactones are cyclic carboxylic esters. Examples include γ-decalactone, which has a characteristic peach flavour, and δ-decalactone, which has a creamy coconut/peach flavour.

FRUITY CREAMY SWEET MILKY BUTTERY NUTTY COCONUT GOURMAND

lactone, cyclic carboxylic ester

Type: Ingredient
Olfactive family: Fruity
Subfamily: Stone fruits
Cluster: Mixed fruit notes
Source: Found in nature (fruit, dairy products, oak wood) and made by synthesis
Chemical class: Lactone (cyclic carboxylic ester)

Instruments

Pyramid

TTop

HHeart

BBase

—Strength

Very powerful and persistent (delta-decalactone)

Very powerful and persistent (delta-decalactone)

Tenacity on blotter

100hours · 4 days

1 h6 h24 h3 d7 d400 h

Scent

Most gamma lactones have fruity scents. γ-Decalactone has a fruity, peach-like odour. γ-Undecalactone has a strong fruity odor like peaches. δ-Decalactone is intensely coconut-like, with creamy, sweet, milky and buttery nuances. The fruity undertones of δ-decalactone recall peach nectar and nectarine, alongside subtle herbal and nutty facets. The S-enantiomer of δ-decalactone has a nutty odor with a fruity undertone. γ-Nonalactone smells of intense, sweet coconut with fruity-peach undertones. δ-Nonalactone is creamy, fatty and milky, with coumarin undertones that the gamma form lacks. Lactones with short chains of six to eight carbons lean herbaceous, and those with nine to eleven carbons give stone fruit notes such as peach, apricot and plum. Macrocyclic lactones have odors similar to macrocyclic ketones of animal origin such as muscone and civetone.

In PREMIEREPEAU

DISCOVERY SET7 × 2 ml →EXTRAIT DE PARFUMThe seven extraits →

The Full Story

Lactones are formed by lactonization, the intramolecular esterification of the corresponding hydroxycarboxylic acids. They can be saturated or unsaturated. Macrocyclic lactones are known as macrolactones.

Lactones are usually named after the precursor acid, with a -lactone suffix and a Greek letter prefix. The prefixes also indicate the size of the lactone ring: a γ-lactone has a 5-membered ring and a δ-lactone a 6-membered ring.

Lactone rings occur widely as building blocks in nature. Five-membered γ-lactones and six-membered δ-lactones are prevalent. Lactones are present in oak wood, and they contribute to the flavour profile of barrel-aged beers. γ-Decalactone is naturally present in many fruits and fermentations. δ-Decalactone naturally occurs in traces in fruit and milk products. In peach the R and S enantiomers of δ-decalactone occur in a ratio of 97.0 : 3.0, and in raspberry in a ratio of 2.2 : 97.8.

The equilibrium constant of the hydrolysis of a lactone is lower than that of a straight-chained ester. Lactones can be reduced to diols using lithium aluminium hydride. Lactones also react with amines to give the ring-opened alcohol and amide. Some lactones convert to polyesters, and the double lactone called lactide polymerizes to polylactic acid. Polycaprolactone is an important plastic.

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Related: Acerola · Akebia Fruit · Allyl Amyl Glycolate · Arctic Bramble · Argan · Berries · Black Sapote · Buriti

Did You Know?

The name lactone derives from lactide, a ring compound formed by the dehydration of lactic acid, and lactic acid takes its name from its original isolation from soured milk. The R-enantiomer of δ-decalactone is the main component of the warning stench of the North American porcupine.

Extraction & Chemistry

Extraction method

Many methods of ester synthesis can also be applied to the synthesis of lactones. γ-Lactones are so stable that 4-hydroxy acids spontaneously cyclize. For longer hydroxy acids and for the strained β-lactones, lactonization competes with polymerization. δ-Decalactone can be obtained from both chemical and biological sources. Chemically, δ-decalactone is produced from the Baeyer-Villiger oxidation of delfone, and from biomass it can be produced by the hydrogenation of 6-pentyl-α-pyrone. A synthetic process for manufacturing optically active δ-decalactone has been developed, and its R and S enantiomers are sold commercially.

Formula: Class of cyclic esters (e.g., gamma-decalactone C₁₀H₁₈O₂, delta-decalactone C₁₀H₁₈O₂)
CAS: N/A — class of compounds (e.g., gamma-decalactone CAS 706-14-9, gamma-undecalactone CAS 104-67-6)
Appearance: Colorless to pale yellow liquid (gamma-decalactone)
Odour strength: Very powerful and persistent (delta-decalactone)
Lasting power: Beyond 100 hours (delta-decalactone)
Synonyms: lactone, cyclic carboxylic ester

IFRA status

See note

No IFRA Standard for the material itself (51st Amendment)

Physical properties

Flash point: 148 °C, open cup (delta-decalactone)

In Perfumery

Lactones contribute significantly to the flavor of fruit and of unfermented and fermented dairy products, and are therefore used as flavors and fragrances. γ-Decalactone is particularly important in the formulation of peach, apricot and strawberry flavourants for drinks, food, personal care products, pharmaceutical drugs and household goods. Several gamma lactones are used commercially. γ-Decalactone has the functional class of a flavouring agent, and δ-decalactone has FEMA GRAS number 2361. Optically active δ-decalactone makes it possible to reproduce natural flavors and fragrances that racemic compounds cannot.

Role in the formula

01modifier

02backbone

03signature note

04blender

05volume builder

Available as

synthetic natural