10032-02-7

Usage

Uses

Used in Fragrance Industry:
GERANYL CAPROATE is used as a fragrance ingredient for its distinct rose-geranium scent with a strong undertone of pineapple and banana, adding a pleasant and unique aroma to various products.
Used in Flavor Industry:
GERANYL CAPROATE is used as a flavoring agent for its ability to impart a fruity and floral taste to food and beverages, enhancing the overall sensory experience of the products.
Used in Cosmetics and Personal Care Industry:
GERANYL CAPROATE is used as an additive in cosmetics and personal care products for its pleasant aroma, which can provide a sensory benefit and improve the overall user experience.

Preparation

By an exchange reaction between methyl caproate and geraniol in the presence of a catalyst or sodium methylate.

InChI:InChI=1/C16H28O2/c1-5-6-7-11-16(17)18-13-12-15(4)10-8-9-14(2)3/h9,12H,5-8,10-11,13H2,1-4H3/b15-12+

Synthetic route

Geraniol (106-24-1) + 2,2'-bipyridyl-6-yl hexanoate (75178-10-8) → geraniol hexanoate (10032-02-7) + <2,2'-bipyridin>-6(1H)-one (101001-90-5)

Conditions	Yield
With cesium fluoride In acetonitrile for 7h; Heating;	A 88% B n/a

Geraniol (106-24-1) + Caproamide (628-02-4) → geraniol hexanoate (10032-02-7)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In n-heptane at 100℃; for 24h;	85%

Geraniol (106-24-1) + hexanoic acid (142-62-1) → geraniol hexanoate (10032-02-7)

Conditions	Yield
With sodium hydroxide at 80℃; for 8h;	76.72%
In water at 30℃; for 18h; lipase from Penicillium cyclopium; Yield given;
With rapeseed lipase acetone powder In hexane at 40℃; for 48h; Enzymatic reaction;

Nerol (106-25-2) + n-hexanoic anhydride (2051-49-2) → geraniol hexanoate (10032-02-7) + (Z)-3,7-dimethyl-2,6-octadienyl ester hexanoic acid (68310-59-8)

Conditions	Yield
With lipase from hog pancreas In diethyl ether at 20℃; Product distribution; Rate constant; also with other lipases; other solvents;

Geraniol (106-24-1) + hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) → geraniol hexanoate (10032-02-7)

Conditions	Yield
With Pseudomonas sp. lipase PS In hexane at 30℃; for 24h; also DL-citronellol and tributyrin; effect of enzyme load, concentration of reagents, addtion of water and pH; var. temp. and solvents;

Upstream product

• 106-25-2 Nerol 
• 2051-49-2 n-hexanoic anhydride 
• 106-24-1 Geraniol 
• 75178-10-8 2,2'-bipyridyl-6-yl hexanoate 
• 142-62-1 hexanoic acid 
• 621-70-5 hexanoic acid, 1,2,3-propanetriyl ester 
• 628-02-4 Caproamide 

Relevant academic research and scientific papers

STEREOSELECTIVE LIPASE-CATALYSED ACYLATION OF TERPENIC ALLYLIC ALCOHOLS BY FATTY ACID ANHYDRIDES

Lipase from pancreatic powder preferentially catalyses the acylation of the E isomer of terpenic allylic alcohols using fatty acid anhydrides as the acylating agent.The course of the reaction can be described by a first-order equation.

The potential use of geraniol esters from citronella oil as anticancer agent

Geraniol which is mainly contained in citronella oil is one of the Indonesian natural products with anticancer potential. In this study, synthesis of geranyl butyrate, geranyl caproate, and geranyl caprylate from geraniol was conducted using sodium hydroxide as a catalyst.The aim was to enhance the anticancer activity of geraniol as a starting material. In order to achieve this, its esters were identified through the use of Gas Chromatography-Mass Spectroscopy (GCMS), Fourier Transform Infra Red (FTIR), Thin Layer Chromatography (TLC), and Proton Nuclear Magnetic Resonance (1H-NMR).They were analyzed for their potential as anticancer agents through Brine Shrimp Lethality Test (BSLT) against Artemia salina Leach, Mosmann method against murine leukemia (P388) cells and normal (Vero) cells. It was found that geraniol esters have the potential to be anticancer compounds. This was indicated by LC50 values of 0.96-1.46 μg/ml against A. salina L, IC50 values of 22.34-32.29 μg/ml against P388 cells, and very less cytotoxic effect on Vero cells with IC50 values of 116.08-172.93 μg/ml. Therefore, there is an expectation that acyclic ester compounds should be used in treating cancer.

Lipase PS-catalyzed transesterification of citronellyl butyrate and geranyl caproate: Effect of reaction parameters

Pseudomonas sp. lipase PS was immobilized by adsorption and tested for its ability to catalyze the synthesis of citronellyl butyrate and geranyl caproate by transesterification in n-hexane. The reaction parameters investigated were: enzyme load, effect or

A USEFUL METHOD FOR SELECTIVE ACYLATION OF ALCOHOLS USING 2,2'-BIPYRIDYL-6-YL CARBOXYLATE AND CESIUM FLUORIDE

Primary and secondary alcohols are acylated under mild conditions by the of use 2,2'-bipyridyl-6-yl carboxylates and cesium fluoride.Furthermore, the reaction is successfully applied to selective acylation of a primary carbinol group of diols containing primary and secondary carbinol groups or exclusive O-acylation of aromatic amino alcohols.

Scandium triflate catalyzed ester synthesis using primary amides

A scandium triflate (ScOTf)3 catalyzed methodology has been developed to synthesize esters from primary amides. Various primary and secondary aliphatic alcohols have been shown to react in n-heptane with a range of primary amides for 24 h.

Optimized synthesis of (Z)-3-hexen-1-yl caproate using germinated rapeseed lipase in organic solvent

(Z)-3-hexen-1-yl esters are important green top-note components of food flavors and fragrances. Effects of various process conditions on (Z)-3-hexen-1-yl caproate synthesis employing germinated rapeseed lipase acetone powder in organic solvent were investigated. Rapeseed lipase catalyzed ester formation more efficiently with non-polar compared to polar solvents despite high enzyme stability in both types of solvents. Maximum ester yield (90%) was obtained when 0.125 M (Z)-3-hexen-1-ol and caproic acid were reacted at 25 °C for 48 h in the presence of 50 g/L enzyme in heptane. Enzyme showed little sensitivity towards aw with optimum yield at 0.45, while added water did not affect ester yield. Esterification reduced by increasing molecular sieves (>0.0125%, w/v). The highest yields of caproic acid were obtained with isoamyl alcohol (93%) followed by butanol and (Z)-3-hexen-1-o1 (88%) respectively reflecting the enzyme specificity for straight and branched chain alcohols. Secondary alcohols showed low reactivity, while tertiary alcohol had either very low reactivity or not esterified at all. A good relationship has been found between ester synthesis and the solvent polarity (log P value); while no correlation for the effect of solvents on residual enzyme activity was observed. It may be concluded that germinated rapeseed lipase is a promising biocatalyst for the synthesis of valuable green flavor note compound. The enzyme also showed a wide range of temperature stability (5-50 °C).