| Identification | More | [Name]
Allyl hexanoate | [CAS]
123-68-2 | [Synonyms]
2-PROPENYL HEXANOATE
2-Propenyl n-hexanoate
ALLYL CAPROATE
ALLYL HEXANOATE
ALLYL N-HEXANOATE
CAPROIC ACID ALLYL ESTER
FEMA 2032
HEXANOIC ACID ALLYL ESTER
Propylene caproate
Allylcapronate
allyle
allylecaproate
Allylester kyseliny kapronove
allylesterkyselinykapronove
Allylhexylate
Hexanoicacid,2-propenylester
ALLYL HEXANOATE 98+% NATURAL FCC
ALLYL HEXANOATE 98+% FCC
AllylHexanoate(PerfumeryGrade)
Allyl hexanoate, 98+% | [EINECS(EC#)]
204-642-4 | [Molecular Formula]
C9H16O2 | [MDL Number]
MFCD00038339 | [Molecular Weight]
156.22 | [MOL File]
123-68-2.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLOURLESS LIQUID | [Melting point ]
-57.45°C (estimate) | [Boiling point ]
75-76 °C/15 mmHg (lit.) | [density ]
0.887 g/mL at 25 °C(lit.)
| [vapor pressure ]
2.69hPa at 25℃ | [FEMA ]
2032 | [refractive index ]
n20/D 1.424(lit.)
| [Fp ]
151 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
0.06g/l | [form ]
neat | [color ]
Colorless to Almost colorless | [Odor]
at 10.00 % in dipropylene glycol. sweet fruity pineapple tropical ethereal rum arrack fatty cognac | [Odor Type]
fruity | [Water Solubility ]
PRACTICALLY INSOLUBLE | [JECFA Number]
3 | [LogP]
3.191 at 20℃ | [Uses]
Allyl Hexanoate is a liquid flavoring agent with a strong pineapple
odor and pale yellow color. it is practically insoluble in propylene
glycol and miscible with alcohol, most fixed oils, and mineral oil.
it is obtained by chemical synthesis. it can be used alone or in com-
bination with other flavoring substances or adjuvants. it is also
termed allyl caproate. | [CAS DataBase Reference]
123-68-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Hexanoic acid, 2-propenyl ester(123-68-2) | [EPA Substance Registry System]
123-68-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N | [Risk Statements ]
R22:Harmful if swallowed.
R24:Toxic in contact with skin.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2810 6.1/PG 3
| [WGK Germany ]
2
| [RTECS ]
MO6125000
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29159080 | [Safety Profile]
Poison by ingestion and skin contact. Mutation data reported. An irritant to human skin. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALLYL COMPOUNDS and ESTERS | [Toxicity]
The acute oral LD50 in rats was 218 mg/kg and in guinea-pigs 280 mg/kg . The acute dermal LD50 for sample no. 71-20 was reported as 0-3ml/kg in the rabbit |
| Questions And Answer | Back Directory | [Chemical Properties]
Colorless to pale yellow liquid; pineapple aroma; Soluble in organic solvents; insoluble in water.
| [Uses]
1. Allyl hexanoate is Used for the preparation of pineapple and other fruit flavors.
2. China provides that allyl hexanoate is the spices temporally allowed to use, which is commonly used in the modulation of food spices and tobacco spices with the flavor of strawberry, apricot, peach, sweet orange, pineapple, apple and other fruit. The use amount of allyl hexanoate is according to the normal production needs, such as 210 mg/kg in chewing gum, 32mg/kg in confectionery, 25 mg/kg in baked goods and 11 mg/kg in cold drinks.
3. Allyl caproate finds use in perfumes as a part of fruity top notes in combination with green mossy notes. it may form a characteristic part of the fragrance. It also tends to round off the Aldehyde notes in combination with styrallyl esters. it has found extensive use in apple, apricot, orange, peach, pineapple, rum, strawberry, tutti-frutti, etc.
4. Widely used in the preparation of food flavors, spices, tobacco flavors and pineapple and other fruit flavors, and also used as an organic synthesis of intermediates. | [Use limits]
FEMA (mg/kg): soft drinks 7.0; cold drinks 11.0; candy 32; baked food 25; pudding class 22; | [Production method]
synthesis of allyl hexanoate
(1) solid acid catalytic method: Add 23.2 g (0.4 mol) of propenol, 23.2 g (0.2 mol) of hexanoic acid, 0.1 g of hydroquinone, 3.0 g of solid super TiO2/SO4-2 and 30 mL of toluene into a 150 mL flask. Heat for reflux for 1.5h and the generated water were taken out by the azeotropic agent toluene. The reaction solution was cooled and filtered, and the solid acid could be repeatedly used after being dried. Add 0.1g of cuprous chloride in the filtrate, and then distillate them to collect the fraction of 186-188 ° C. The obtained finished products was 27.1g with a yield of 86.9%, and the refractive index n20d was 1.4241.
(2) sulfuric acid catalytic method: Firstly, hexanoic acid and allyl alcohol performed esterification in catalysis of sulfuric acid. After the end of the reaction, the above esters were washed with water and then were neutralized with 15% Na2CO3 solution and washed with water to neutral. Add anhydrous sodium carbonate or anhydrous calcium chloride for dehydration. Finally, Allyl hexanoate were obtained by further filtration and vacuum distillation. | [Hazards & Safety Information]
Category Toxic substances
Toxicity classification high toxicity
Acute toxicity peritoneal-rat LD50: 218 mg/kg; Oral-guinea pig LD50: 280 mg/kg
Stimulation Data Skin-human 20 mg/48 h mild
Flammability Hazardous characteristics
Flammable; Combustion produces irritating fumes
Storage and transportation characteristics
Stored in the low-temperature, well-ventilated and dry warehouse; stored separately with food raw materials
Fire extinguishing agent
dry powder, foam, sand, carbon dioxide, mist water |
| Hazard Information | Back Directory | [Occurrence]
Allyl hexanoate has also been reported to occur naturally in baked potato, mushroom and pineapples. | [Definition]
ChEBI: 2-Propenyl hexanoate is a fatty acid ester. | [Preparation]
Allyl hexanoate is directly esterified by hexanoic acid and allyl alcohol under the catalysis of sulfuric acid, and then neutralized, washed with water and rectified to obtain the finished product. | [Taste threshold values]
Taste characteristics at 10 ppm: sweet, fresh, juicy, pineapple and fruity | [General Description]
Allyl hexanoate is a volatile flavoring compound with a pineapple flavor. It is naturally found in pineapple, baked potatoes and mushrooms. Allyl hexanoate is used as a flavoring agent in chewing gum, candies and baked goods. | [Metabolism]
Clapp, Kaye & Young (1969) have reported on the metabolism of allyl
compounds in the rat. These compounds react with reduced glutathione in the liver and the
resultant product, after hydrolysis and N-acetylation gives rise to the mercapturic acid,
which is readily excreted in the urine. |
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