66512-92-3

Usage

Natural Occurrence

Found in citrus fruits and lemongrass.

Physical State

Colorless liquid.

Aroma

Strong, citrusy scent.

Industrial Use

Widely used in fragrance and flavor industries.

Flavoring Agent

Used in foods and beverages.

Fragrance Use

Utilized in perfumes, soaps, and candles.

Antimicrobial Property

Effective against various microorganisms.

Insecticidal Property

Repels and eliminates insects.

Household & Personal Care

Popular ingredient in cleaning and care products.

Therapeutic Effects

Possesses anti-inflammatory, antioxidative, and anti-cancer properties.

InChI:InChI=1/C12H22O2/c1-10(2)5-4-6-11(3)9-12-13-7-8-14-12/h5,11-12H,4,6-9H2,1-3H3

Upstream product

• 106-23-0 3,7-dimethyl-oct-6-enal 
• 107-21-1 ethylene glycol 

Relevant academic research and scientific papers

Synthesis and characterization of some oxidized derivatives of citronellal ethylene acetal

Three pairs of geometrical isomers corresponding to allylic monooxidation products of the trisubstituted olefin, citronellal ethylene acetal (3), were synthesized.These compounds were the E and Z isomers of 7-(1,3-dioxolan-2-yl)-2,6-dimethyl-2-hepten-1-ol, -1-al, and -1-oic acid (methyl ester), precursors for identifying the biodegradation products from citronellal and some of its derivatives.The E aldehyde (4) was obtained from 3 by the Sharpless procedure with catalytic quantities of selenium dioxide.The E ester (5) and E alcohol (6) were prepared in high isomeric purity (97-99percent) from 4 with activated manganese dioxide and sodium borohydride, respectively.Selective ozonolysis of the isobutenyl group in 3 gave 5-(1,3-dioxolan-2-yl)-4-methyl-1-pentanal (7).Under the conditions used, ozone did not react with the ethylene acetal group.Acetal aldehyde (7) was stereoselectively converted to the Z alcohol (8) by a Wittig reaction.Manganese dioxide oxidation of 8 (98-99percent Z isomer) to the Z aldehyde (9) and of 9 to the Z ester (10) was accompanied by partial Z to E isomerization.The distribution of E and Z isomers in crude reaction mixtures was determined by gas chromatography with a glass capillary column or by proton magnetic resonance spectroscopy.

Organocatalytic epoxidation and allylic oxidation of alkenes by molecular oxygen

Pyrrole-proline diketopiperazine (DKP) acts as an efficient mediator for the reduction of dioxygen by Hantzsch ester under mild conditions to allow the aerobic metal-free epoxidation of electron-rich alkenes. Mechanistic crossovers are underlined, explaining the dual role of Hantzsch ester as a reductant/promoter of the DKP catalyst and a simultaneous competitor for the epoxidation of alkenes when HFIP is used as a solvent. Expansion of this protocol to the synthesis of allylic alcohols was achieved by adding a catalytic amount of selenium dioxide as an additive, revealing a superior method to the classical application of t-BuOOH as a selenium dioxide oxidant.

AN EFFICIENT SbCl3-METAL SYSTEM FOR ALLYLATION, REDUCTION AND ACETALIZATION OF ALDEHYDES

SbCl3-Fe or SbCl3-Al could induce allylation of aldehydes with allylic halides at room temperature to give high yields of the corresponding homoallylic alcohols with high regio- and chemoselectivity.SbCl3-Al or SbCl3-Zn in DMF-H2O was found to be an efficient reduction system for conversion of aldehydes to alcohols at room temperature in excellent yields.While alcohol was used as solvent instead of DMF-H2O, the acetalization product was obtained in almost quantitative yield.Catalytic amount of SbCl3 was effective for this purpose.This acetalization method could also be applied to ketone.