102-22-7

Basic information

• Product Name: GERANYL PHENYLACETATE
• Synonyms: GERANYL PHENYLACETATE;FEMA 2516;TRANS-3 7-DIMETHYL-2 6-OCTADIEN-1-YL PHENYLACETATE;(2E)-3,7-Dimethyl-2,6-octadienyl phenylacetate;3,7-dimethyl-2,6-octadienylester,(e)-benzeneaceticaci;3,7-dimethyl-2,6-octadienylester,(E)-Benzeneaceticacid;Acetic acid, phenyl-, 3,7-dimethyl-2,6-octadienyl ester, (E)-;Benzeneacetic acid, 3,7-dimethyl-2,6-octadienyl ester, (E)-
• CAS NO: 102-22-7
• Molecular Formula: C₁₈H₂₄O₂
• Molecular Weight: 272.38
• EINECS: 203-014-7
• Product Categories: Alphabetical Listings;Flavors and Fragrances;G-H
• Mol File: 102-22-7.mol

Chemical Properties

• Boiling Point: 278 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.972 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.45E-06mmHg at 25°C
• Refractive Index: n20/D 1.509(lit.)
• Water Solubility: 92.8μg/L at 25℃
• CAS DataBase Reference: GERANYL PHENYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: GERANYL PHENYLACETATE(102-22-7)
• EPA Substance Registry System: GERANYL PHENYLACETATE(102-22-7)

Safety Data

• WGK Germany: 2
• RTECS: CY1595900
• Hazardous Substances Data: 102-22-7(Hazardous Substances Data)

Usage

Uses

Used in Flavoring Industry:
GERANYL PHENYLACETATE is used as a flavoring agent for its honey and rose-like odor, providing a unique taste and aroma to various food and beverage products.
Used in Perfumery Industry:
GERANYL PHENYLACETATE is used as a fixative in rose compositions and heavy perfumes, enhancing the longevity and intensity of the fragrance.
Used in Aroma Industry:
With its aroma characteristics of foral, powdery, rosy, honey, and dried fruit-like notes accompanied by balsamic undernotes at 2.0% concentration, GERANYL PHENYLACETATE is utilized in the creation of various aromas for different applications.

Preparation

By the esterification of geraniol with phenylacetyl chloride.

Flammability and Explosibility

Notclassified

Safety Profile

Low toxicity by ingestion and sktn contact. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C18H24O2/c1-15(2)8-7-9-16(3)12-13-20-18(19)14-17-10-5-4-6-11-17/h4-6,8,10-12H,7,9,13-14H2,1-3H3/b16-12+

Upstream product

• 106-24-1 Geraniol 
• 75178-11-9 Phenyl-acetic acid [2,2']bipyridinyl-6-yl ester 
• 103-82-2 phenylacetic acid 

Downstream Products

• 103-82-2 phenylacetic acid 

Relevant articles and documents

Gd(OTf)3-catalyzed synthesis of geranyl esters for the intramolecular radical cyclization of their epoxides mediated by titanocene(III)

A selective and mild method for the esterification of a variety of carboxylic acids with geraniol is developed. We demonstrated that the use of triphenylphosphine, I2, 2-methylimidazole or imidazole and a catalytic amount of Gd(OTf)3 resulted to be more active than the previous protocols, providing a 16-membered library of geranyl esters in higher yields and in shorter reaction times. The use of essential oil of palmarosa (Cymbopogon martinii), enriched with geraniol, as a raw material for the synthesis of the target compounds complemented and proved how sustainable and eco-friendly this protocol is. Finally, the selective 6,7-epoxidation of the obtained geranyl esters led us to study their regio-controlled radical cyclization mediated by titanocene(iii) for the synthesis of novel (8-hydroxy-9,9-dimethyl-5-methylene cyclohexyl)methyl esters in moderate yields and with excellent stereoselectivities.

Stereoselectivity of additions to N-methyl acetonitrilium fluorosulfonate

Alkoxy-N-methyl-acetiminium salts were prepared by addition of CH 3OH and C2H5OH to N-methyl acetonitrilium fluorosulfonate at low temperature. Analysis of the 5JHH and 3J13C-H coupling constants in the NMR spectra showed an anti addition with a diastereoselectivity of >95%. Deprotonation of these salts with (Z)-configuration gave the corresponding N-methyl-alkoxyacetimines with very high (E)-configuration. Upon protonation at -78 °C, these iminoesters gave the corresponding alkoxy-N-methyl-acetiminium salts with (E)-configuration. Computational analyses of the iminoesters and the corresponding iminium cations including the conformations give insight into the relative stability. Nitrilium salts can be used as reagents, exemplified by some esterifications between simple acids and alcohols.

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.