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Allyl cyclohexanepropionate

HCID 17617
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Basic information

CAS
2705-87-5
Standard SMILES
C=CCOC(=O)CCC1CCCCC1
InChIKey
TWXUTZNBHUWMKJ-UHFFFAOYSA-N
Molecular formula
C12H20O2
Average molar mass
196.29 g/mol
Monoisotopic mass
196.14632988

Overview

Allyl cyclohexylpropionate is a fatty acid ester.

Names & identifiers

Preferred name
Allyl cyclohexanepropionate
IUPAC
prop-2-enyl 3-cyclohexylpropanoate
English name
Allyl cyclohexylpropionate
Molecular formula
C12H20O2
Molecular weight
196.29

Names & synonyms

2705-87-5Allyl cyclohexanepropionateAllyl cyclohexylpropionateAllyl 3-cyclohexylpropionateCyclohexanepropanoic acid, 2-propenyl ester3-Allylcyclohexyl propionateProp-2-en-1-yl 3-cyclohexylpropanoateAllyl hexahydrophenylpropionateAllyl beta-cyclohexylpropionateprop-2-enyl 3-cyclohexylpropanoateFEMA No. 20262-Propenyl cyclohexanepropanoate
Show more names
FEMA 2026Pineapple estePineapple esterALLYLCYCLOHEXYL PROPIONATE3-allyl-cyclohexanopropionateAnanolideohexanepropionateAllylcyclohxylpropionate
CYCLOHEXANEPROPIONIC ACID, ALLYL ESTERCyclohexanol, 3-allyl-, propionate2-Propen-1-yl cyclohexanepropionateEINECS 220-292-5Cyclohexanepropanoic acid, 2-propen-1-yl esterDTXSID8044755BRN 2254663H4W9H3L241

Database identifiers

CAS
2705-87-5
PubChem CID
17617
DTXSID
DTXSID8044755
ChEMBL
CHEMBL3184129
ChEBI
CHEBI:31188
UNII
H4W9H3L241
EC Number
220-292-5
Nikkaji
J3.039B

Properties

Computed structural properties

XLogP
3.8
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
6
Heavy atoms
14
Formal charge
0
Complexity
181

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Wax monoesters [FA0701]
Fragrances · 2 items

Fragrance substance (Allyl 3-cyclohexylpropionate) -> IFRA amendment 51

Fragrance Ingredient (Allyl cyclohexanepropionate) -> IFRA transparency List

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.945-0.950
Flavoring AgentsEU Flavoring substances
Solubility · 2 items

Soluble in ether, higher oils and fatty oils. Insoluble in glycerine and water

1ml in 4ml 80% ethanol (in ethanol)

Boiling Point · 2 items

91.00 °C. @ 1.00 mm Hg

91 °C (1mm Hg)

Refractive Index1.457-1.462
Physical Description · 2 items

Liquid; CBI

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H302 (99.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P332+P317, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2014 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

Hazard information

Regulatory Information · 5 items

Chemical: Cyclohexanepropanoic acid, 2-propenyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Cyclohexanepropanoic acid, 2-propen-1-yl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanepropanoic acid, 2-propen-1-yl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: Allyl 3-cyclohexylpropionate (EC: 220-292-5)

Allyl 3-cyclohexylpropionate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Aliphatic allyl esters: Human health tier II assessment
Hazard Classes and Categories · 2 items

Acute Tox. 4 (99.9%)

Acute toxicity (ingestion) - category 3

Safety data

wgk
2
tsca

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular

Uses & manufacturing

U.S. Production2023: 8,500,000 - <10,000,000 lb
Consumer UsesFragrance
Industry UsesFragrance
IFRA Fragrance Standards · 6 items

Allyl 3-cyclohexylpropionate

Allyl 3-cyclohexylpropionate; 2-Propen-1-yl cyclohexanepropionate; Allyl 3-cyclohexylpropanoate; Allyl beta-cyclohexylpropionate; Allyl β-cyclohexylpropionate; Allyl cyclohexanepropionate; Allyl cyclohexylpropionate; Allyl hexahydrophenylpropionate; Cyclohexanepropionic acid, 2-propenyl ester; Prop-2-enyl 3-cyclohexylpropanoate; Cyclohexylpropionic acid allyl ester

IFRA_STD_238.pdf

51

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Restriction: This material should be used only in the limited quantity as stated in the Standard_Specification: This material should be used only if it meets the criteria stated in the Standard

Household ProductsInformation on 120 consumer products that contain Allyl Cyclohexylpropionate in the following categories is provided:
Use Classification · 3 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 2 items

Plastics Material and Resin Manufacturing

Cyclohexanepropanoic acid, 2-propen-1-yl ester: ACTIVE

Restriction Limits in the Finished Product (%) · 6 items

Related reactions

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Compound notes

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Colourless liquid with a pineapple odour

Physicochemical properties

Melting point
-20 ° · <-20°
Boiling point
91 °C1 · 91 °C1 mm Hg(lit.)
Density
0.948 g/mL · 0.948 g/mL at 25 °C(lit.)
vapor pressure
3.8 Pa · 3.8Pa at 25℃
refractive index
20 · n20/D 1.46(lit.)
FEMA
2026 · 2026 | ALLYL CYCLOHEXANEPROPIONATE
FLAVIS Number
9.498 · 09.498 | Allyl cyclohexanepropionate
Flash point
227 °F · 227 °F
storage temp.
Inert atmosphere,Room Temperature
solubility
almost transparency in Methanol
color
Colorless to Almost colorless
Odor
100 % · at 100.00 %. sweet pineapple tropical fruity candy waxy
Odor Type
fruity
biological source
synthetic
Water Solubility
16.5 mg/L · 16.5mg/L at 20℃
JECFA Number
13 · 13
Major Application
cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
Cosmetics Ingredients Functions
PERFUMING
InChI
1S/C12H20O2/c1-2-10-14-12(13)9-8-11-6-4-3-5-7-11/h2,11H,1,3-10H2
InChIKey
TWXUTZNBHUWMKJ-UHFFFAOYSA-N
SMILES
C=CCOC(=O)CCC1CCCCC1
LogP
4.276 at · 4.276 at 20℃
CAS DataBase Reference
2705 · 2705-87-5(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
ALLYL CYCLOHEXANEPROPIONATE
FDA 21 CFR
172.515 · 172.515
FDA UNII
4 W9H3L241 · H4W9H3L241
NIST Chemistry Reference
2 · Cyclohexanepropanoic acid, 2-propenyl ester(2705-87-5)
EPA Substance Registry System
Allyl cyclohexanepropionate (2705-87-5)
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
302 · H302+H312+H332-H317-H410
Precautionary statements
261 · P261-P273-P280-P301+P312-P302+P352+P312-P304+P340+P312
Hazard Codes
Xn
Risk Statements
20 · 20/21/22
Safety Statements
36 · 36/37/39-45
RIDADR
2810 · 2810
WGK Germany
2 · 2
RTECS
6735000 · GV6735000
TSCA
TSCA listed
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
29162090 · 29162090
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Sens. 1
Toxicity
50 has · The acute oral LD50 has been reported as 585 mg/kg in the rat (Br & Griepentrog, 1967).
REACH Registrations
Active
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
TSCA listed
rtecs
GV6735000
ridadr
2810
hs_code
29162090
Toxicity
The acute oral LD50 has been reported as 585 mg/kg in the rat (Br & Griepentrog, 1967).
risk_code
20/21/22
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
Xn
safety_code
36/37/39-45
hazard_class
6.1(b)
Storage Class
10 - Combustible liquids
packing_group
III
Hazard statements
H302+H312+H332-H317-H410
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Sens. 1
Precautionary statements
P261-P273-P280-P301+P312-P302+P352+P312-P304+P340+P312

0.085 [Products applied to the lips]

0.025 [Products applied to the axillae]

0.35 [Products applied to the face/body using fingertips]

0.47 [Products related to fine fragrances]

0.12 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]

0.12 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]

Applications · 3 items

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

OccurrenceApparently has not been reported to occur in nature.

UsesAllyl 3-Cyclohexylpropanoate is used in preparation of a new type of environmentally friendly paint thinner. It useful as a topnote ingredient in certain perfume types, also as a modifier for already existing materials: Allyl caproate, Linalylacetate, Methyl phenyl carbinyl propionate, Sweet Orange oil, etc. More important in flavors: this chemical is often the chief carrier of the fruity note in imitation Pineapple, and an interesting modifier in imitation Strawberry, Raspbe~, etc. A powerful fortifier in the popular “tutti- -frutti” flavor types. Concentration in perfumes: usually less than 1% of the composition. Concentration in flavors: 10 to 40 ppm in finished food products, somewhat higher in chewing gum and certain candies.

Preparation methods

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

Upstream & downstream products

Upstream raw materials

Cyclohexanepropionic acidAlcohol solubleAllyl alcohol

Additional notes

DefinitionChEBI: Allyl cyclohexylpropionate is a fatty acid ester.