706-14-9

Basic information

• Product Name: gamma-Decalactone
• Synonyms: DECALACTONE (GAMMA);G-DECALACTONE;GAMMA-HEXYL-GAMMA-BUTYROLACTONE;GAMMA-HYDROXYCAPRIC ACID LACTONE;GAMMA-(+)-DECALACTONE;GAMMA-DECALACTONE;GAMMA-DECANOLACTONE;FEMA 2360
• CAS NO: 706-14-9
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• EINECS: 211-892-8
• Product Categories: lactone flavors;Cosmetics;Food Additive
• Mol File: 706-14-9.mol

Chemical Properties

• Boiling Point: 281 °C
• Flash Point: >230 °F
• Appearance: clear colourless to pale yellow liquid
• Density: 0.953 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00852mmHg at 25°C
• Refractive Index: n20/D 1.449
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: 1.26g/L at 20℃
• BRN: 117547
• CAS DataBase Reference: gamma-Decalactone(CAS DataBase Reference)
• NIST Chemistry Reference: gamma-Decalactone(706-14-9)
• EPA Substance Registry System: gamma-Decalactone(706-14-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• RTECS: LU4600000
• TSCA: Yes
• Hazardous Substances Data: 706-14-9(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
Gamma-Decalactone is used as a flavoring agent for its creamy, fatty, oily, buttery sweet, coconut, fruity, and peach-like taste characteristics at 10 ppm. It is particularly favored for its peach flavor, which is highly sought after in the industry.
Used in Perfumery:
Gamma-Decalactone is used as a fragrance ingredient for its intensely fruity odor, which is well-suited for heavy, fruity flower odors and aroma compositions.
Used in Food and Beverage Industry:
Gamma-Decalactone is used as an additive in the food and beverage industry to impart a peach-like flavor and aroma to various products, enhancing their taste and overall sensory experience.
Used in Analytical Chemistry:
Gamma-Decalactone may be used as an analytical reference standard for the quantification of the analyte in fruit beverages using different chromatography techniques, aiding in the quality control and authentication of these products.
Occurrence:
Gamma-Decalactone is a naturally occurring compound found in various fruits such as peach, apricot, and strawberry, as well as in other food items like butter, milk, beer, rum, red and white wine, mango, bilberry, plums, prunes, and cheeses. Its presence in these foods contributes to their distinct and appealing flavors and aromas.

Preparation

Naturalγ-decalactone is produced biotechnologically starting from ricinoleic acid, which is degraded by β-oxidation to 4-hydroxydecanoic acid, which lactonizes at lower pH to yield γ-decalactone

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 462, 1990 DOI: 10.1021/jo00289a016Synthetic Communications, 18, p. 2241, 1988 DOI: 10.1080/00397918808082366

Flammability and Explosibility

Notclassified

Synthesis

By heating γ-bromocapric acid in a sodium carbonate solution; by prolonged heating of 9-decen-1-oic acid with 80% H2SO2 at 90°C

InChI:InChI=1/C10H18O2/c1-2-3-4-5-6-9-7-8-10(11)12-9/h9H,2-8H2,1H3/t9-/m0/s1

Upstream product

• 111-71-7 heptanal 
• 623-71-2 ethyl 3-chloropropanoate 
• 106-14-9 R-12-hydroxyoctadecanoic acid 
• 188964-99-0 methyl 2,4-dichlorooctanoate 
• 57196-88-0 methyl 2,2,4-trichlorodecanoate 
• 64-17-5 ethanol 
• 111-66-0 oct-1-ene 
• 144-48-9 iodacetamide 
• 37810-94-9 decane-1,4-diol 
• 108-24-7 acetic anhydride 
• 1356451-39-2 C₁₀H₁₇BrO 
• 27907-00-2 dec-1-yn-4-ol 
• 1117-86-8 1,2-octandiol 
• 105-53-3 diethyl malonate 

Downstream Products

• 77461-95-1 4-Phenylselanyl-decanoic acid 
• 37810-94-9 decane-1,4-diol 
• 112-37-8 undecylenic acid 
• 43160-78-7 4-oxodecanal 
• 710-04-3 6-hexyltetrahydro-2H-pyran-2-one 
• 3208-32-0 2-hexyltetrahydrofuran 
• 259675-63-3 Succinic acid mono-[(S)-1-(2-benzylcarbamoyl-ethyl)-heptyl] ester 
• 107797-27-3 (-)-(S)-γ-Decalactone 
• 107797-26-2 (R)-5-Hexyl-dihydro-furan-2-one 
• 259675-58-6 4-hydroxy-decanoic acid benzylamide 
• 17369-51-6 4-hydroxydecanoic acid 
• 2602-61-1 N,N-diethyldecanamide 
• 63095-33-0 γ-(Z)-dec-7-enlactone 
• 25564-22-1 2-pentyl-2-cyclopenten-1-one 

Relevant articles and documents

Photo-induced radical borylation of hemiacetals via C–C bond cleavage

In this study, we reported a photo-induced radical borylation of hemiacetal derivatives via C–C bond cleavage. This transformation can be realized under mild conditions with simple reaction settings and irradiation of visible light. A series of substrates, including both cyclic and linear hemiacetal derivatives, were effectively transformed to the borylation product in moderate to good yields. Finally, the mechanism was studied in detail by DFT calculations, suggesting insight of the radical borylation process.

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

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.

W(OTf)6-Catalyzed Synthesis of Γ-Lactones by Ring Contraction of Macrolides or Ring Closing of Terminal Hydroxyfatty Acids in Ionic Liquid

γ-Lactones are an important class of fine chemical products and are widely used in perfumes, medicines, pesticides, dyes, and other fields. Herein, a new method for γ-lactones preparation based on ring contraction was developed. Starting from macrolides, W(OTf)6 was used to catalyze the ring-opening polymerization then depolymerization. The depolymerization step was not a common ring-closing process, and the carbon number of the ring was reduced one by one by rearrangement to form the most thermodynamically stable five-membered ring compounds. γ-Caprolactone (180 °C for 10 h) was obtained in a yield of 94 % when [EMIM]OTf was used as the solvent, and the yield of isolated product was up to 85 %. The interaction of various components and the reaction mechanism were studied by FTIR spectroscopy and 1H NMR spectroscopy, respectively. Furthermore, γ-lactones could be produced when the substrate was extended to terminal hydroxyfatty acids. Unexpectedly, the catalyst was poisoned by 1 equivalent of H2O added during the process and thus the yield decreased greatly. The reaction is green and simple, and proceeds in one pot with high atom economy (100 % for macrolides and with water as the only byproduct for terminal hydroxyfatty acid), which provides a promising approach to synthesizing γ-lactones.

Nucleo-Palladation-Triggering Alkene Functionalization: A Route to γ-Lactones

An unprecedented strategy for the highly effective synthesis of γ-lactones from homoallylic alcohols was achieved by palladium catalysis in one step. The protocol affords aryl, alkyl, and spiro γ-lactones directly from readily available homoallylic alcohols in good yields with excellent functional group tolerance and high chemoselectivity under mild conditions.

Transforming Olefins into γ,δ-Unsaturated Nitriles through Copper Catalysis

We have developed a strategy to transform olefins into homoallylic nitriles through a mechanism that combines copper catalysis with alkyl nitrile radicals. The radicals are easily generated from alkyl nitriles in the presence of the mild oxidant di-tert-butyl peroxide. This cross-dehydrogenative coupling between simple olefins and alkylnitriles bears advantages over the conventional use of halides and toxic cyanide reagents. With this method, we showcase the facile synthesis of a flavoring agent, a natural product, and a polymer precursor from simple olefins.

MnO2-promoted carboesterification of alkenes with anhydrides: A facile approach to γ-lactones

An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.

1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents

The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents

The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

Ruthenium pincer-catalyzed synthesis of substituted γ-butyrolactones using hydrogen autotransfer methodology

The ruthenium pincer-catalyzed synthesis of γ-butyrolactones from 1,2-diols and malonates using borrowing-hydrogen methodology is reported. This regioselective domino-process takes place through catalytic C-C bond formation, followed by intramolecular transesterification. Herein, we show the Ru-MACHO-BH complex as a valuable catalyst in hydrogen autotransfer reactions.

Direct room-temperature lactonisation of alcohols and ethers onto amides: An "amide strategy" for synthesis

Last-minute deal: A direct lactonisation of ethers and alcohols onto amides that proceeds at room temperature under mild conditions is reported (see scheme). This allows the effective saving of up to two unproductive, sequential deprotection operations in synthetic sequences. Mechanistic studies are described, and a new "amide strategy" that exploits the dual robustness/late-stage selective activation properties of this functional group is outlined. Copyright