Jasmolactone

What it is

Jasmolactone is a member of the class of 2-pyranones: tetrahydro-2H-pyran-2-one carrying a pent-2-en-5-yl group at position 6.

Chemistry

Chemically, jasmolactone is 5-hydroxy-8-decenoic acid delta-lactone. Its IUPAC name is 6-(pent-3-en-1-yl)oxan-2-one. The (E) form is named 6-[(E)-pent-3-enyl]oxan-2-one.

Lactones are formed by lactonization, the intramolecular esterification of the corresponding hydroxycarboxylic acids. The prefix delta marks a six-membered lactone ring. Both (E)-jasmolactone and (Z)-jasmolactone are classed as forms of jasmolactone. Jasmolactone is insoluble in water and soluble in alcohol.

The lactone family

Lactones are cyclic carboxylic esters derived from the corresponding hydroxycarboxylic acids. They contribute significantly to the flavour of fruit and of dairy products, and are therefore used as flavours and fragrances. δ-Decalactone, for example, has a creamy coconut and peach flavour.

Occurrence

Jasmolactone is recorded as a plant metabolite of Jasminum multiflorum.

Related molecule

Jasminlactone is a different molecule, (Z)-7-decen-5-olide, with the CAS number 25524-95-2. Jasminlactone is more floral and less fruity-lactonic than Jasmolactone Delta.

Safety and regulation

A safety assessment of the material found it not genotoxic. It is not expected to be phototoxic or photoallergenic. It was found not to be persistent, bioaccumulative and toxic under the IFRA Environmental Standards. The Joint FAO/WHO Expert Committee on Food Additives found no safety concern at current levels of intake when it is used as a flavouring agent. Exposure is below the Threshold of Toxicological Concern for a Cramer Class II material for repeated dose, reproductive and local respiratory toxicity. Read-across to the related 5-hydroxy-7-decenoic acid δ-lactone shows no skin sensitization concern at current declared levels of use. Hazard notifications classify it as Eye Irritation category 2 in 80.2% of cases.

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