Jasmolone

Jasmolone
Names
	Preferred IUPAC name 4-Hydroxy-3-methyl-2-[(2E)-pent-2-en-1-yl]cyclopent-2-en-1-one
	Other names Jasmolone; Jasmololone; Jasmololon
Identifiers
CAS Number	54383-66-3;
3D model (JSmol)	Interactive image;
PubChem CID	5374699;
	SMILES CCC=CCC1=C(C(CC1=O)O)C;
Properties
Chemical formula	C11H16O2
Molar mass	180.247 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Jasmolone is an irregular monoterpene. Irregular monoterpenes are derived from two isoprene C5 units, but do not follow the usual head-to-tail coupling mechanism. Jasmolins are found in pyrethrum flowers. They can specifically be found in the flower heads of Chrysanthemum cinerariaefolium. Jasmolins act as an insecticide for the flower.^[1] It is found in the cytoplasm of plants.^[2]

Jasmolone is part of the secondary alcohol family. Jasmolone is found in the alcohol portion of pyrethrins. It is thought that jasmolone is a derivative of cyclized and altered fatty acids. The cyclization of the fatty acids is similar to the biosynthetic pathway cyclization of prostaglandins.

A precursor of jasmolone could be alpha-linolenic acid with a 12-oxophytodienoic acid intermediate. The chain shortening could be produced by a beta-oxidation then a decarboxylation.

12-Oxophytodienoic acid is also used in the production of jasmonic acid. Jasmonic acid is used in the production of secondary metabolites in a plants signaling system. Jasmonic acid is used in a plant's response to a microbial infection or wound.

Natural production[]

Jasmolone is one of the three alcohols (along with and ) needed in combination with two specific acids (chrysanthemic acid and ) to form insecticidal esters. These six insecticidal esters are part of the pyrethrins family. So far, pyrethrins have been found in Chrysanthemum cinerariaefolium, Tagetes erecta, , Tagetes minuta, , Calendula officinalis, and Zinnia elegans. Pyrethrins are found mostly in the head of the flowers, but have also been found in the callus tissue of the flowers.^[3]

Biosynthesis[]

α-Linolenic acid undergoes a radical oxidation with O₂ and lipoxygenase to form a peroxide. Lipoxygenase is an iron-containing enzyme that is used to catalyze dioxygenation of polyunsaturated fatty acids in this case, α-linolenic acid. Lipooxygenase specifically binds to polyunsaturated fatty acids that have a cis,cis-1,4-pentadiene present. Next, an allene oxide synthase occurs followed by allene oxide cyclase. 12-Oxophytodienoic acid is formed. It is unknown how jasmolone is formed from 12-oxophytodienoic acid after this step.

Biosynthesis of jasmolone

Laboratory synthesis[]

(Z)-Jasmolone was synthesized by Jacqueline Ficini and Jean Pierre Genet in June 1975.

Jasmolone production

References[]

^ R.Dewick, “Medicinal Natural Products: A Biosynthetic Approach”, United Kingdom: John Wiley & Sons Ltd, 2009, 204-5.
^ Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
^ K.Ramawat, J.Merillon, “Biotechnology: Secondary Metabolites Plants and Microbes”, Boca Raton: CRC Press Taylor & Francis Group, 2007, 136.

[1] R.Dewick, “Medicinal Natural Products: A Biosynthetic Approach”, United Kingdom: John Wiley & Sons Ltd, 2009, 204-5.

[2] Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

[3] K.Ramawat, J.Merillon, “Biotechnology: Secondary Metabolites Plants and Microbes”, Boca Raton: CRC Press Taylor & Francis Group, 2007, 136.

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