123-68-2 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 123-68-2 differently. You can refer to the following data:
1. Colorless to pale yellow liquid; pineapple aroma; Soluble in organic solvents; insoluble in water.
2. Allyl hexanoate is a colorless to slightly yellow transparent liquid with fruity sweet, pineapple-like taste and fruit-like aroma (pineapple). It has been shown to occur in pineapple. It has a typical pineapple odor and is used in, for example, pineapple flavors.
Uses
Different sources of media describe the Uses of 123-68-2 differently. You can refer to the following data:
1. 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.
2. 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.
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
Occurrence
Allyl hexanoate has also been reported to occur naturally in baked potato, mushroom and pineapples.
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.
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
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.
Check Digit Verification of cas no
The CAS Registry Mumber 123-68-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 3 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 123-68:
(5*1)+(4*2)+(3*3)+(2*6)+(1*8)=42
42 % 10 = 2
So 123-68-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H16O2/c1-3-5-6-7-9(10)11-8-4-2/h4H,2-3,5-8H2,1H3
123-68-2Relevant articles and documents
Synthesis of allyl esters of fatty acids and their ovicidal effect on Cydia pomonella (L.)
Escriba, Marc,Barbut, Montserrat,Eras, Jordi,Canela, Ramon,Avilla, Jesus,Balcells, Merge
, p. 4849 - 4853 (2009)
Eight allyl esters of fatty acids were synthesized in moderate to high yields with a novel two-step procedure using glycerol as a starting material. The two-step methodology avoids the use of allyl alcohol. The first step consisted of heating at 80 °C for 48 h a 2:1:5 mmol mixture of glycerol, a fatty acid, and chlorotrimethylsilane in a solvent-free medium. The crude compound was then dissolved in butanone and heated at 115 °C in the presence of Nal. A tandem Finkelstein rearrangement-elimination reaction occurs, producing the corresponding allyl ester. The activity of these esters against Cydia pomonella (L.) (Lepidoptera: Tortricidae) eggs was tested in the laboratory by topical application of one 0.1 μL drop. All of the compounds showed a concentration-mortality response and caused 100% mortality at the highest concentration tested (10 mg/mL). There was an inverse relationship between the alkyl chain length and the ovicidal activity of the allyl ester; the LC50 and the LC90 of the two compounds that have the longer alkyl chains were significantly higher than those of the rest of the compounds. The ovicidal and IGR activities of this kind of compound appear to be unprecedented.
An efficient iron catalyzed regioselective acylative cleavage of ethers: Scope and mechanism
Bodduri, V.D. Vijaykumar,Choi, Kyung-Min,Vaidya, Raghavender Rao,Patil, Kalpesh,Chirumarry, Sridhar,Jang, Kiwan,Yoon, Yong-Jin,Falck, John R.,Shin, Dong-Soo
supporting information, p. 7089 - 7093 (2015/12/01)
A method involving iron catalyzed acylative cleavage of cyclic and acyclic ethers with acyl/aroyl chlorides has been studied to produce chloroesters and esters respectively. Examination of the scope revealed that less electron rich alkyl group in unsymmetric, acyclic ether was acylated while the chloride derived from the counterpart moiety was volatile and difficult to isolate. In contrast, α-branched cyclic ethers were converted to the corresponding primary ester and secondary chloride. Steric hindrance of ether also plays an important role in acylative C-O bond cleavage. The mechanism of ether cleavage is proposed to involve a single electron initiated SN1 dissociative pathway.
Practical preparation of esters and thioacetates from alkyl halides and carboxylates or thioacetate catalyzed by PEG400 without solvent
Cao, Yu-Qing,Wu, Guo-Qiang,Li, Ya-Bin,Dai, Zhi,Chen, Bao-Hua
, p. 3353 - 3358 (2007/10/03)
Carboxylic esters and thioacetates were conveniently prepared in good to excellent yields under mild conditions by the reaction of alkyl halides with sodium carboxylates or sodium thioacetate catalyzed by PEG400 in the absence of solvents. Copyright Taylor & Francis Group, LLC.
