Low sclareol by‐product of clary sage concrete: chemical analysis of a waste product of the perfume industry

Laville, Rémi; Castel, Cécilia; Fattarsi, K.; Roy, Céline; Legendre, Laurent; Delbecque, Claire; Garry, Pierre-Philippe; Audran, Arthur; Fernández, Xavier

doi:10.1002/ffj.3133

Cited by 3 publications

(2 citation statements)

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“…This structural similarity has made sclareol the most promising starting material for semisynthesis production of ambrafuran [ 5 , 44 ]. The main industrial extraction procedure to isolate sclareol from clary sage involves hydro-distillation of the aerial parts of the plant, followed by solvent extraction of the remaining plant material [ 45 ].…”

Section: Synthesis Starting From Diterpenes: the Bicyclic Labdanesmentioning

confidence: 99%

Ambrafuran (AmbroxTM) Synthesis from Natural Plant Product Precursors

2020

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Ambergris, an excretion product of sperm whales, has been a valued agent in the formulation of perfumes. The composition of ambergris consists of two major components: 40–46% cholestanol type steroids and approximately 25–45% of a triterpenoid known as ambrein. Ambergris undergoes oxidative decomposition in the environment to result in odorous compounds, such as ambraoxide, methylambraoxide, and ambracetal. Its oxidized form, ambrafuran (IUPAC name: 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran), is a terpene furan with a pleasant odor and unique olfactive and fixative properties. The current state of the fragrance industry uses ambrafuran materials entirely from synthetic or semisynthetic sources. However, natural compounds with the potential to be converted to ambergris-like odorants have been extracted from several different types of plants. Here we review plant terpenoids suitable as starting materials for the semisyntheses of ambrafuran or intermediates, such as ambradiol, that can be used in biocatalytic transformations to yield ambrafuran.

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Section: Synthesis Starting From Diterpenes: the Bicyclic Labdanesmentioning

confidence: 99%

Ambrafuran (AmbroxTM) Synthesis from Natural Plant Product Precursors

2020

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“…Sclareol is the starting material for synthesizing ambergris-like odorants Ambrox ® , a valuable compound used in perfumery, and in cleaning products and household care (air fresheners, disinfectants, laundry detergents) 16 . Utilization of residual biomass after distillation and EO production of clary sage for further conversion into value-added products such as sclareol, and other diterpenes (sclerenbol, ambecler, hetabrol, and tabeceron) is a known and applied technique [17][18][19] .…”

Section: Introductionmentioning

confidence: 99%

Comparison of Volatile Compounds from Clary Sage (Salvia sclareaL.) Verticillasters Essential Oil and Hydrolate

Aćimović

Lončar

Jeliazkov

et al. 2022

Journal of Essential Oil Bearing Plants

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The volatile compounds of essential oil (EO) and corresponding hydrolate (HY) extracted by steam distillation from clary sage (Salvia sclarea L.) cv "Domaća mirisna" grown in Serbia were identified using gas chromatography/mass spectrometry (GC/MS). The most abundant compounds of EO were linalyl acetate (43.5%) and linalool (25.9%), followed by α-terpineol, germacrene D, and geranyl acetate. In the corresponding HY (recovered water-soluble fraction of EO) the dominant were linalool (63.3%) and α-terpineol (26.8%), followed by geraniol.These differences in composition between clary sage EO and HY could be explained by linalyl acetate's low water solubility. Clustering of 55 clary sage EO accessions (from literature) shows the presence of several chemotypes: linalyl acetate+linalool, linalyl acetate+sclareol, linalool+geranyl acetate, germacrene D+β-caryophyllene, caryophyllene oxide, and three unspecified chemotypes (geranyl acetate, methyl chavicol, and α-terpineol). According to this classification, clary sage cv "Domaća mirisna" belongs to a moderate linalyl acetate chemotype (between 19.8 and 45.7%). Further investigations need to focus on clary sage HY and their potential applications because HYs could increase economic gain as a by-product. However, their utilization for other purposes (cosmetic, postharvest fruit processing, organic agriculture, etc.) could be a safe solution for wastewater produced during EO distillation.

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