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104-50-7

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104-50-7 Usage

Description

y-Octalactone has a strong, fruity odor reminiscent of coconut with a very sweet taste. This substance may be prepared synthetically from epoxy-1,2-hexane and sodio-malonic ester; after saponification the oxyacid is extracted with ether and is lactonized.

Chemical Properties

Different sources of media describe the Chemical Properties of 104-50-7 differently. You can refer to the following data:
1. γ-Octalactone has a fruity odor reminiscent of coconut and a very sweet taste.
2. CLEAR COLOURLESS LIQUID
3. gamma-Octanoic lactone occurs as an aroma constituent in many processed and unprocessed foods. It is a pale yellow liquid with a fruity/coconut-like odor and is used both in aroma compositions and in heavy blossom perfumes.

Occurrence

Reported found in apricot, peach, blue cheese, butter, cooked chicken and cooked pork, licorice, milk, raspberry, roasted barley, and roasted filbert.

Uses

Different sources of media describe the Uses of 104-50-7 differently. You can refer to the following data:
1. 4-Octanolide is one of the fine organic aerosol emitted from meat cooking operations that was examined by high-resolution gas chromatography.
2. (Gamma)-Octalactone is a synthetic flavoring agent that is a stable, colorless to slightly yellow liquid of peach odor. It should be stored in glass or tin containers. It is used in flavors for peach with applications in baked goods, candy, and ice cream at 5–17 ppm.

Aroma threshold values

Detection: 7 ppb; aroma characteristics at 1.0%: sweet, fatty, creamy, coconut, lactonic and coumarinic.

Taste threshold values

Taste characteristics at 1 to 10 ppm: coconut, fatty, creamy, coumarinic, with a strong creamy and waxy mouthfeel.

Synthesis Reference(s)

Chemistry Letters, 23, p. 53, 1994The Journal of Organic Chemistry, 52, p. 4319, 1987 DOI: 10.1021/jo00228a032Tetrahedron Letters, 19, p. 419, 1978 DOI: 10.1016/S0040-4039(01)91443-1

General Description

γ--Octalactone is one of the flavor constituents of peaches, oranges and sweet fortified wines.

Flammability and Explosibility

Notclassified

Safety Profile

Mildly toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

Prepared synthetically from epoxy-1,2-hexane and sodio-malonic ester; after saponification, the oxyacid is extracted with ether and is lactonized.

Check Digit Verification of cas no

The CAS Registry Mumber 104-50-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 104-50:
(5*1)+(4*0)+(3*4)+(2*5)+(1*0)=27
27 % 10 = 7
So 104-50-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3/t7-/m0/s1

104-50-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A18142)  gamma-Octanolactone, 98%   

  • 104-50-7

  • 25g

  • 629.0CNY

  • Detail
  • Alfa Aesar

  • (A18142)  gamma-Octanolactone, 98%   

  • 104-50-7

  • 100g

  • 1914.0CNY

  • Detail
  • Sigma-Aldrich

  • (51573)  γ-Octalactone  analytical standard

  • 104-50-7

  • 51573-100MG

  • 1,628.64CNY

  • Detail
  • Aldrich

  • (O4008)  γ-Octanoiclactone  97%

  • 104-50-7

  • O4008-25G

  • 654.03CNY

  • Detail

104-50-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name gamma-Octanoic lactone

1.2 Other means of identification

Product number -
Other names 2(3H)-Furanone, 5-butyldihydro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:104-50-7 SDS

104-50-7Relevant articles and documents

FREE RADICAL ADDITION OF α-BROMOCARBOXYLIC ACIDS TO OLEFINS LEADING TO γ-BUTYROLACTONES

Nakano, Taichi,Kayama, Mikio,Matsumoto, Hideyuki,Nagai, Yoichiro

, p. 415 - 418 (1981)

Benzoyl peroxide-catalyzed free radical addition of bromoacetic, α-bromopropionic, and α-bromobutyric acids to olefins took place under mild conditions to afford γ-alkyl-, γ-alkyl-α-methyl-, and γ-alkyl-α-ethyl-γ-butyrolactones in good yields.

Synthesis of deuterated γ-lactones for use in stable isotope dilution assays

Hislop, J.O.-Anna,Hunt, Martin B.,Fielder, Simon,Rowan, Daryl D.

, p. 7075 - 7083 (2004)

Two syntheses of deuterated γ-lactones for use as internal standards in stable isotope dilution assays (SIDA) were developed. [2,2,3,3- 2H4]-γ-Octa-, -γ-deca-, and -γ-dodecalactones with >89% deuterium incorporation were prepared in 27, 17, and 19% overall yields, respectively, by the reduction of a doubly protected hydroxypropiolic acid with deuterium gas. [3,3,4-2H 3]-γ-Octa- and -γ-dodecalactones were prepared in 6 and 23% yields with >92% deuterium incorporation by the free radical addition of 2-iodoacetamide to [1,1,2-2H3]-1-hexene and [1,1,2- 2H3]-1-decene, respectively. Reaction yields were highly dependent upon the purity of the 1-alkene starting material. The deuterated γ-lactones were evaluated as internal standards for SIDA.

Intermolecular additions of α-boryl radicals

Batey, Robert A.,Pedram, Bijan,Yong, Kelvin,Baquer, Gemma

, p. 6847 - 6850 (1996)

The utility of α-boryl radicals 1 in intermolecular addition processes is described. Boronic ester substituted radicals are shown to add to both electron deficient and electron rich radical traps, and give high yields of homoallylboronic esters in radical allylation reactions.

-

Terai,Tanaka

, p. 822 (1956)

-

-

Okano,M.

, p. 1041 - 1046 (1976)

-

A mild biosynthesis of lactones via enantioselective hydrolysis of hydroxynitriles

Pollock, Julie A.,Clark, Karen M.,Martynowicz, Bethany J.,Pridgeon, Matthew G.,Rycenga, Matthew J.,Stolle, Kristen E.,Taylor, Stephen K.

, p. 1888 - 1892 (2007)

We have developed a biocatalytic method to produce lactones and related compounds via the enzymatic hydrolysis of γ- and β-hydroxynitriles. The synthesis is a mild, general, and environmentally friendly way to enantioselectively hydrolyze nitriles with commercially available nitrilase enzymes. The synthesis of four pheromones is demonstrated via a one-step method.

Calcium(II)- And Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol

Qi, Chenxiao,Yang, Shengwen,Gandon, Vincent,Leb?uf, David

supporting information, p. 7405 - 7409 (2019/10/02)

We report an efficient intramolecular hydroacyloxylation of unactivated alkenes, offering a streamlined access to relevant γ-lactones, which features the utilization of either a calcium(II) salt or triflimide as a catalyst in hexafluoroisopropanol. This method could be applied to the synthesis of natural products and the late-stage functionalization of natural and bioactive molecules. Additionally, DFT computations were used to elucidate the twist of reactivity observed between the hydroamidation and hydroacyloxylation of unactivated alkenes regarding the formation of 5- and 6-membered rings.

Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams

Kise, Naoki,Hamada, Yusuke,Sakurai, Toshihiko

, p. 1143 - 1156 (2017/02/18)

The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the adducts as methyl 4-aryl-4-((4-methoxyphenyl)amino)butanoates. The adducts were transformed to 5-aryl-γ-butyrolactams by cyclization with NaH and subsequent oxidation with CAN. (±)-Norcotinine was prepared from nicotinaldehyde by this method. The electroreductive coupling of aromatic ketones and aldimines with acrylonitrile in the presence of TMSCl gave 4-aryl-4-(trimethylsiloxy)butanenitriles and 4-aryl-4-((4-methoxyphenyl)amino)butanenitriles, respectively.

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