13058-12-3

Basic information

• Product Name: ETHYL GERANATE
• Synonyms: ETHYL GERANATE;RARECHEM AL BI 0142;ethyl 3,7-dimethylocta-2,6-dienoate;2,6-Octadienoic acid, 3,7-dimethyl-, ethyl ester;ETHYL3,7-DIMETHYL-2,6-OCTADIENOATE;2,6-Octadienoic acid, 3,7-dimethyl-, ethyl ester 6-octadienoic acid, 3,7-dimethyl- ethyl ester 2,6-Octadienoic acid,3,7-dimethyl-,ethyl ester;3,7-Dimethyl-2,6-octadienoic acid ethyl ester;Ai3-25079
• CAS NO: 13058-12-3
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• EINECS: 235-948-6
• Mol File: 13058-12-3.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 266.1°Cat760mmHg
• Flash Point: 119.8°C
• Appearance: /
• Density: 0.904g/cm³
• Vapor Pressure: 0.00881mmHg at 25°C
• Refractive Index: 1.458
• CAS DataBase Reference: ETHYL GERANATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL GERANATE(13058-12-3)
• EPA Substance Registry System: ETHYL GERANATE(13058-12-3)

Safety Data

• Hazardous Substances Data: 13058-12-3(Hazardous Substances Data)

Usage

General Description

Ethyl geranate is a chemical compound that is commonly used in the fragrance and flavor industry. It is a clear, colorless liquid with a fruity, sweet, and floral aroma. Ethyl geranate is found naturally in various fruits, including raspberries, peaches, and oranges. It is often used as a scent component in perfumes, soaps, and personal care products. In addition to its use in the fragrance industry, ethyl geranate is also utilized as a flavor enhancer in food and beverages, adding a fruity, sweet taste to products such as candy, chewing gum, and beverages. It is generally recognized as safe for use in food by the US Food and Drug Administration.

InChI:InChI=1/C12H20O2/c1-5-14-12(13)9-11(4)8-6-7-10(2)3/h7,9H,5-6,8H2,1-4H3

Upstream product

• 105540-76-9 1-Ethoxy-3,7-dimethyloct-6-en-1-yn-3-ol 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 51318-62-8 ethyl 4-bromo-3-methylcrotonate 
• 870-63-3 prenyl bromide 
• 20608-08-6 diethyl phosphonoacetic acid 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 131489-39-9 1-<(trimethylsilyl)oxy>-1-ethoxy-3-methyl-1,3-butadiene 
• 14502-38-6 ethyl 3-methyl-6-oxohex-2E/Z-enoate 
• 1530-33-2 isopropyltriphenylphosphonium bromide 
• 996-82-7 sodium diethylmalonate 
• 112157-80-9 (E)-3,7-Dimethyl-6-phenylsulfanyl-octa-2,7-dienoic acid ethyl ester 
• 79858-00-7 α-sulfinyl citronellate 
• 92511-62-1 ethyl 3-methyl-4-(tributylstannyl)-2-butenoate 

Downstream Products

• 459-80-3 geranic acid 
• 106-25-2 Nerol 
• 5944-27-4 ethyl 3,7-dimethyloctanoate 
• 624-15-7 geraniol 
• 106-24-1 Geraniol 
• 105-90-8 geranyl propionate 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 109-20-6 [(2E)-3,7-dimethylocta-2,6-dienyl] 3-methylbutanoate 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 142747-09-9 2-(1-hydroxymethyl-2,6,6-trimethyl-2-cyclohexenyl)ethanol 
• 142747-10-2 3-(1-hydroxymethyl-2,6,6-trimethyl-2-cyclohexenyl)propanol 
• 142747-06-6 ethyl (1-ethoxycarbonyl-2,6,6-trimethyl-2-cyclohexenyl)acetate 
• 142747-07-7 ethyl 3-(1-ethoxycarbonyl-2,6,6-trimethyl-2-cyclohexenyl)propionate 
• 96849-99-9 ethyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate 

Relevant articles and documents

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INSECT PHEROMONES AND THEIR ANALOGUES XXX. SYNTHESIS OF OCTA-2E,6E-DIENE-1,8-DIOL DIISOVALERATE - THE SEX PHEROMONE OF Agriotes tauricus

The synthesis has been effected of octa-2E,6E-diene-1,8-diol diisovalerate - the sex pheromone of the Crimean click beetle Agriotes tauricus - by the carboxymethylenation of the readilly available 6-methylhept-5-en-2-one, the allyl oxidation of a terminal methyl group, reduction of the ester fraction, and interaction of the diol so obtained with isovaleryl chloride.The required pheromone can also bee obtained from available cyclic oligomers of isoprene.

Transition-Metal-Free Formylation of Allylzinc Reagents Leading to α-Quaternary Aldehydes

The first example of formylation of allylzinc reagents using S-phenyl thioformate is presented. The reaction proceeded under mild conditions without any transition-metal catalyst, forming quaternary carbon centers with reactive functionalities, such as formyl and vinyl groups. Moreover, Barbier-type formylation of an allylic bromide with a sterically demanding thioformate was achieved. As a preliminary result, asymmetric formylation was conducted using a menthol-derived chiral thioformate.

Conformational Analysis, Thermal Rearrangement, and EI-MS Fragmentation Mechanism of (1(10)E,4E,6S,7R)-Germacradien-6-ol by 13C-Labeling Experiments

An uncharacterized terpene cyclase from Streptomyces pratensis was identified as (+)-(1(10)E,4E,6S,7R)-germacradien-6-ol synthase. The enzyme product exists as two interconvertible conformers, resulting in complex NMR spectra. For the complete assignment of NMR data, all fifteen (13C1)FPP isotopomers (FPP=farnesyl diphosphate) and (13C15)FPP were synthesized and enzymatically converted. The products were analyzed using various NMR techniques, including 13C, 13C COSY experiments. The (13C)FPP isotopomers were also used to investigate the thermal rearrangement and EI fragmentation of the enzyme product. All 15 isotopomers of (13C1)- and fully labeled (13C15)farnesyl diphosphate were synthesized and converted to the title compound by a newly characterized bacterial terpene cyclase from Streptomyces pratensis. The enzyme products were used for structure elucidation of the sesquiterpene alcohol, full assignment of NMR data and a conformational analysis, and investigation of its Cope rearrangement and of its EI-MS fragmentation mechanism.