27751-90-2

Usage

InChI:InChI=1/C13H22O2/c1-5-13(14)15-10-9-12(4)8-6-7-11(2)3/h7,9H,5-6,8,10H2,1-4H3/b12-9+

Upstream product

• 106-25-2 Nerol 
• 79-03-8 propionyl chloride 
• 106-24-1 Geraniol 
• 802294-64-0 propionic acid 
• 105-38-4 vinyl propionate 
• 74-85-1 ethene 
• 201230-82-2 carbon monoxide 
• 123-62-6 propionic acid anhydride 
• 624-15-7 geraniol 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 57745-83-2 (Z)-1,7-dihydroxy-3,7-dimethyl-2-octene 
• 105-37-3 Ethyl propionate 
• 13058-12-3 ethyl 3,7-dimethyl-2,6-octadienoate 
• 104857-56-9 Propionic acid (E)-3,7-dimethyl-7-(2,2,2-trifluoro-acetoxy)-oct-2-enyl ester 

Relevant academic research and scientific papers

Palladium-Catalyzed Direct Dicarbonylation of Amines with Ethylene to Imides

The selective and effective conversion of low-cost and simple bulk chemicals into high value-added products through catalytic strategy has a wide range of practical significance. Here, a palladium-catalyzed method for the direct and efficient dicarbonylation of amines with basic industrial feedstock ethylene to imide has been developed. Moderate to excellent yields of the desired imides can be produced from readily available amines in a straightforward manner.

New neryl esters from Helichrysum italicum (Roth) G. Don (Asteraceae) essential oil

Helichrysum italicum (immortelle) is a dwarf aromatic shrub native to the Mediterranean region. The typical subspecies (italicum) produces an essential oil rich in neryl acetate and characteristic β-diketones, italidiones, highly valued in the perfume industry. As esters are an important group of aroma-active volatiles, herein the composition of the ester fraction of this immortelle chemotype essential oil was studied in detail. Chromatographic separation of Corsican immortelle essential oil enabled the discovery of numerous potentially olfactory-interesting esters of nerol and/or angelic acid, undetectable by direct GC-MS analyses of the unfractioned oil. Four esters of nerol and medium-chain branched fatty acids represent new natural products, while several other esters have a rather restricted occurrence in the Plant Kingdom.

Efficient Enzymatic Preparation of Flavor Esters in Water

A straightforward biocatalytic method for the enzymatic preparation of different flavor esters starting from primary alcohols (e.g., isoamyl, n-hexyl, geranyl, cinnamyl, 2-phenethyl, and benzyl alcohols) and naturally available ethyl esters (e.g., formate, acetate, propionate, and butyrate) was developed. The biotransformations are catalyzed by an acyltransferase from Mycobacterium smegmatis (MsAcT) and proceeded with excellent yields (80-97%) and short reaction times (30-120 min), even when high substrate concentrations (up to 0.5 M) were used. This enzymatic strategy represents an efficient alternative to the application of lipases in organic solvents and a significant improvement compared with already known methods in terms of reduced use of organic solvents, paving the way to sustainable and efficient preparation of natural flavoring agents.

Formyloxyacetoxyphenylmethane and 1,1-diacylals as versatile O-formylating and O-acylating reagents for alcohols

Formyloxyacetoxyphenylmethane, symmetric 1,1-diacylals and mixed 1-pivaloxy-1-acyloxy-1-phenylmethanes have been used as moisture stable O-formylating and O-acylating reagents for primary and secondary alcohols, allylic alcohols and phenols under solvent/catalyst free conditions to afford their corresponding esters in good yield.

Terpene Cyclizations inside a Supramolecular Catalyst: Leaving-Group-Controlled Product Selectivity and Mechanistic Studies

The tail-to-head terpene cyclization is arguably one of the most complex reactions found in nature. The hydrogen-bond-based resorcinarene capsule represents the first man-made enzyme-like catalyst that is capable of catalyzing this reaction. Based on noncovalent interactions between the capsule and the substrate, the product selectivity can be tuned by using different leaving groups. A detailed mechanistic investigation was performed to elucidate the reaction mechanism. For the cyclization of geranyl acetate, it was found that the cleavage of the leaving group is the rate-determining step. Furthermore, the studies revealed that trace amounts of acid are required as cocatalyst. A series of control experiments demonstrate that a synergistic interplay between the supramolecular capsule and the acid traces is required for catalytic activity.

In situ immobilization of Candida antarctica B lipase in polyurethane foam support

Candida antarctica B (CALB) lipase was immobilized using polyurethane (PU) foam as support by confinement method. This can be a promising technique due to the low cost of the support, simple procedure of immobilization and the possibility of using the derivative as catalyst for the food industry reactions. CALB immobilization on PU was performed using 6 mL polyol and 4 mL isocyanate (60-40%, v/v), with 1 mL of enzymatic solution (0.8 g enzyme in 5 mL distilled water). The immobilization process resulted in a 535% increase in activity for the enzymatic derivative. The enzyme was stable for 360 days at room (10-25 °C) and low (2-8 °C) temperatures, for 300 days at 40 and 60 °C and for 150 days at 80 °C in wet ambient conditions. The synthesis of geranyl propionate and ethyl oleate catalyzed by the immobilized derivative presented conversions of around 97 and 83%, respectively. The immobilized CALB in PU was reused consecutively different behavior occurred which stored in dry ambient conditions at different temperatures (room: 10-25 °C, refrigeration: 2-8 °C and 40 °C) resisted 30 cycles, for both forms of storage, keeping more than 87, 95 and 83% of its activity, respectively.

An examination of the scope and stereochemistry of the Ireland-Claisen rearrangement of boron ketene acetals

The Ireland-Claisen rearrangement of boron ketene acetals is described. The boron ketene acetal intermediates are formed through a soft enolization that obviates the use of strong bases and the intermediacy of alkali metal enolates. Yields and diastereoselectivities of these rearrangements are very sensitive to the choice of boron reagent, even among those that have been shown to effect quantitative formation of boron ketene acetals from esters. The rearrangement occurs at room temperature for all substrates with generally high levels of stereoselectivity. In contrast to previous reports using boron triflates, the use of a commercially available boron iodide reagent allows for a wider substrate scope that extends to propionates and arylacetates, as well as the previously described α-oxygenated esters. This work also provides insight into the dynamic nature of boron ketene acetals and the ramifications of this behavior for reactions in which they are intermediates. Borane down: Boron enolates of allylic esters are efficiently generated at -78 °C using cHx2BI (dicyclohexyliodoborane)·Et3N. These rearrange smoothly on being warmed to room temperature to give generally high diastereoselectivity in forming γ,δ-unsaturated acids (see scheme). The rearrangements provide a key insight into the dynamic nature of boron ketene acetals.

Enzymatic modification of palmarosa essential oil: Chemical analysis and olfactory evaluation of acylated products

We have developed an enzymatic protocol to modify the composition of palmarosa essential oil by acylation of its alcohol components by three different acyl donors at various rates. The resulting modified products were characterized by qualitative and quantitative analyses by gas chromatography, and their olfactory properties were evaluated by professional perfumers. We showed that our protocol resulted in two types of modifications of the olfactory properties. The first and most obvious effect observed was the decrease of the alcohol content, with the concomitant increase of the corresponding esters, along with their fruity notes (pear, most notably). The second and less obvious effect was the expression of notes from minor components ((E)-β-ocimene, linalool, β-caryophyllene, and farnesene), originally masked by the sweet-floral-rose odor of geraniol, present in 70% in the palmarosa essential oil used, and emergence of citrus, green, spicy and clove characters in the modified products. This methodology might be considered in the future as a sustainable route to new natural ingredients for the perfumer. Copyright

A clean enzymatic process for producing flavour esters by direct esterification in switchable ionic liquid/solid phases

A clean biocatalytic approach for producing flavour esters using switchable ionic liquid/solid phases as reaction/separation media has been developed. The phase behaviour of different IL/flavour acetyl ester (geranyl acetate, citronellyl acetate, neryl acetate and isoamyl acetate) mixtures was studied at several concentrations, resulting for all cases in fully homogeneous liquid media at 50 °C, and solid systems at room temperature. By using an iterative centrifugation protocol on the solid IL/flavour ester mixtures at controlled temperatures, the solid IL phase and the liquid flavour ester phase can be easily separated. The excellent suitability of an immobilized Candida antarctica lipase B (Novozym 435) catalyst in the esterification reaction between an aliphatic carboxylic acid (acetic, propionic, butyric or valeric) and a flavour alcohol (isoamyl alcohol, nerol, citronellol or geraniol) in N,N′,N′′,N′′′-hexadecyltrimethyl-ammonium bis(trifluoromethylsulfonyl)imide ([C16tma][NTf2])IL has been demonstrated, the product yield being improved up to 100% under appropriate reaction conditions (enzyme amount, dehydrating molecular sieves, etc.) at 50 °C. The enzymatic synthesis of sixteen different flavour esters was carried out in [C16tma][NTf2] by means of this approach, providing products of up to 0.757 g mL-1 concentration after IL separation. The residual activity of the enzyme/IL system during seven consecutive operation cycles was shown to be practically unchanged after reuse.

Lipase-catalyzed separation of geometrical isomers: Geraniol-nerol

The substrate/lipase ratio as well as pH of the buffer medium played important roles in the resolution of geometrical isomeric mixture of geraniol-nerol. Based on the results, an immobilized lipase from Pseudomonas fluorescens (PFL) was found effective in selective transesterifications whereas Pseudomonas sp. Lipase (PSL) was found to be useful in hydrolyzing the esters. Copyright