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

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

Description

A colorless liquid with pineapple aroma. Used as a flavoring agent or adjuvant.

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).

Usage

Reported uses (ppm): (FEMA, 1994) ▼▲ Food Category? Usual? Max.? Alcoholic beverages? 2.33 5.33 Baked goods? 52.27 71.15 Chewing gum? 9.56 17.21 Frozen dairy? 20.11 28.75 Gelatins, puddings? 21.36 29.81 Gravies? 1 2 Hard candy? 7.41 10 Nonalcoholic beverages? 7.2 13.8 Soft candy? 44.97 57.8

Natural occurrence

Not reported found in nature.

Chemical Properties

Different sources of media describe the Chemical Properties of 2705-87-5 differently. You can refer to the following data:
1. Allyl cyclohexylpropionate has not been found in nature. It is a colorless liquid with a sweet, fruity odor, reminiscent of pineapples.The ester is prepared by esterification of 3-cyclohexylpropionic acid (obtained by hydrogenation of cinnamic acid) with allyl alcohol. It is used in perfumery to obtain fruity top notes as well as pineapple and chamomile nuances.
2. A colorless liquid with pineapple aroma. Used as a flavoring agent or adjuvant

Occurrence

Apparently has not been reported to occur in nature.

Uses

Allyl 3-Cyclohexylpropanoate is used in preparation of a new type of environmentally friendly paint thinner.

Preparation

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

Taste threshold values

Taste characteristics at 30 ppm: fruity, pineapple, waxy, with green sweet apple nuances.

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

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