2705-87-5

Basic information

• Product Name: Allyl cyclohexylpropionate
• Synonyms: 3-allyl-cyclohexanopropionate;3-Allylcyclohexyl propionate;3-allylcyclohexylpropionate;Allyl 3-cyclohexylpropanoate;allyl cyclohexylpropanoate;Allyl hexahydrophenylpropionate;Allylcyclohxylpropionate;allylhexahydrophenylpropionate
• CAS NO: 2705-87-5
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• EINECS: 220-292-5
• Product Categories: monomer;A-B;Alphabetical Listings;Flavors and Fragrances;Allyl Monomers;Monomers;Polymer Science;ester series
• Mol File: 2705-87-5.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 91 °C1 mm Hg(lit.)
• Flash Point: 227 °F
• Appearance: /
• Density: 0.948 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.013mmHg at 25°C
• Refractive Index: n20/D 1.46(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: almost transparency in Methanol
• Water Solubility: 16.5mg/L at 20℃
• CAS DataBase Reference: Allyl cyclohexylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: Allyl cyclohexylpropionate(2705-87-5)
• EPA Substance Registry System: Allyl cyclohexylpropionate(2705-87-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37/39-45
• RIDADR: 2810
• WGK Germany: 2
• RTECS: GV6735000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 2705-87-5(Hazardous Substances Data)

Usage

Description

Allyl cyclohexylpropionate is a colorless liquid with a sweet, fruity odor, reminiscent of pineapples. It is not found in nature and is prepared by esterification of 3-cyclohexylpropionic acid (obtained by hydrogenation of cinnamic acid) with allyl alcohol. Allyl cyclohexylpropionate is used in perfumery to obtain fruity top notes as well as pineapple and chamomile nuances.

Uses

Used in the Paint Industry:
Allyl cyclohexylpropionate is used as an environmentally friendly paint thinner, contributing to the development of a new type of eco-friendly paint products.
Used in the Food Industry:
Allyl cyclohexylpropionate serves as a flavoring agent or adjuvant in various food categories, enhancing the taste and aroma of the products. It is used within specific concentration limits to ensure safety and desired flavor profiles.
Used in Alcoholic Beverages:
Allyl cyclohexylpropionate is used as a flavoring agent in alcoholic beverages, with a usual usage level of 2.33 ppm and a maximum level of 5.33 ppm.
Used in Baked Goods:
In the baked goods industry, Allyl cyclohexylpropionate is used to add a fruity aroma, with a usual usage level of 52.27 ppm and a maximum level of 71.15 ppm.
Used in Chewing Gum:
Allyl cyclohexylpropionate is used as a flavoring agent in chewing gum, with a usual usage level of 9.56 ppm and a maximum level of 17.21 ppm.
Used in Frozen Dairy:
Allyl cyclohexylpropionate is used in frozen dairy products to provide a fruity and pineapple-like aroma, with a usual usage level of 20.11 ppm and a maximum level of 28.75 ppm.
Used in Gelatins and Puddings:
Allyl cyclohexylpropionate is used as a flavoring agent in gelatins and puddings, with a usual usage level of 21.36 ppm and a maximum level of 29.81 ppm.
Used in Gravies:
In the gravy industry, Allyl cyclohexylpropionate is used to add a fruity aroma, with a usual usage level of 1 ppm and a maximum level of 2 ppm.
Used in Hard Candy:
Allyl cyclohexylpropionate is used as a flavoring agent in hard candy, with a usual usage level of 7.41 ppm and a maximum level of 10 ppm.
Used in Nonalcoholic Beverages:
Allyl cyclohexylpropionate is used in nonalcoholic beverages to provide a fruity and pineapple-like aroma, with a usual usage level of 7.2 ppm and a maximum level of 13.8 ppm.
Used in Soft Candy:
In the soft candy industry, this compound is used as a flavoring agent, with a usual usage level of 44.97 ppm and a maximum level of 57.8 ppm.
Taste threshold values:
Allyl cyclohexylpropionate has a fruity, pineapple, waxy taste with green sweet apple nuances at a concentration of 30 ppm.

Identification

▼▲ CAS.No.:? 2705-87-5? FL.No.:? 9.498 FEMA.No.:? 2026 NAS.No.:? 2026 CoE.No.:? 2223 EINECS.No.:? 220-292-5? JECFA.No.:? 13

Regulatory Status

CoE: Used provisionally. Bev.: 10 ppm; Food: 10 ppm FDA: 21 CFR 172.515 FDA (other): n/a JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1996).

Natural occurrence

Not reported found in nature.

Preparation

By direct esterification of cyclohexylpropionic acid with allyl alcohol in the presence of benzene.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes. Combustible liquid. See ALLYL COMPOUNDS and ESTERS

Metabolism

Allyl compounds are metabolized to mercapturic acid which is excreted in the urine (Clapp, Kaye & Young, 1969). Cyclohexylpropionic acid is aromatized to benzoic acid and excreted as hippuric acid in the urine. Substituted cyclohexylcarboxylic acids are either excreted unchanged or completely oxidized (Williams, 1959).

InChI:InChI=1/C12H20O2/c1-3-9-14-12(13)10(2)11-7-5-4-6-8-11/h3,10-11H,1,4-9H2,2H3

Synthetic route

allyl 3-cyclohexylpropionate (2705-87-5) → 3-cyclohexylpropan-1-ol (1124-63-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere;	99%
With sodium In ethanol Heating;

allyl 3-cyclohexylpropionate (2705-87-5) → cyclohexanepropionic acid (701-97-3)

Conditions	Yield
With [2-(dicyclohexylphosphino)ethyl]trimethylammonium chloride; phenylsilane In tetrahydrofuran; water at 20℃; for 2h; Inert atmosphere;	94%

allyl 3-cyclohexylpropionate (2705-87-5) + phenylsilane (694-53-1) → phenylsilanetriyl tris(3-cyclohexylpropanoate)

Conditions	Yield
With [N,N'-(1,2-dimethyl-1,2-ethanediylidene)bis[3-(diphenylphosphino)-1-propanamine]]Ni In benzene-d6 at 25℃; for 3h; Catalytic behavior; Inert atmosphere; Glovebox; Sealed tube;	93%

allyl 3-cyclohexylpropionate (2705-87-5) → oxiran-2-ylmethyl 3-cyclohexylpropanoate

Conditions	Yield
With fluorosulfonyl fluoride; dihydrogen peroxide; potassium carbonate In 1,4-dioxane; water at 20℃; for 1h;	85%

methanol (67-56-1) + allyl 3-cyclohexylpropionate (2705-87-5) → methyl 1-cyclohexylpent-4-enyl-2-carboxylate

Conditions	Yield
With polystyrene-diethylsilane sylil triflate resin; sulfuric acid; triethylamine 1.) CH2Cl2, 25 deg C; 2 h; 2.) THF, 50 deg C, 4 h; 3.) THF, CH2Cl2, 55 deg C, 4 h; Yield given; Multistep reaction;

allyl 3-cyclohexylpropionate (2705-87-5) → cyclohexylpropyl formate (1129-67-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na / ethanol / Heating 2: TsOH / benzene / 18 h / Heating View Scheme

allyl 3-cyclohexylpropionate (2705-87-5) → Di-(3-cyclohexylpropyl)-malonat (1168-85-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na / ethanol / Heating 2: TsOH / benzene / 16 h View Scheme

allyl 3-cyclohexylpropionate (2705-87-5) → naphthalen-1-ylmethyl 2-((1-(3-hydroxypropyl)cyclohexyl)methyl)acrylate

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C / Inert atmosphere 3: tris[2-phenylpyridinato-C2,N]iridium(III); diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / 1,4-dioxane / 3 h / 25 °C / Irradiation; Inert atmosphere View Scheme

allyl 3-cyclohexylpropionate (2705-87-5) → 2-(3-cyclohexylpropoxy)isoindoline-1,3-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme

Downstream Products

• 1129-67-5 cyclohexylpropyl formate 
• 1168-85-0 Di-(3-cyclohexylpropyl)-malonat 
• 701-97-3 cyclohexanepropionic acid 
• 1124-63-6 3-cyclohexylpropan-1-ol