gamma-Decalactone

gamma-Decalactone Basic information
Product Name:gamma-Decalactone
Synonyms:gamma-Decalactone~4-Decanolide~4-Hydroxydecanoic acid gamma lactone;Decanoic acid, gamma-lactone;Decanolactone;Decanolide-1,4;gamma-Hexylbutyrolactone;gamma-n-Decalactone;gamma-n-Hexyl-gamma-butyrolactone;-Hexylbutyrolactone
CAS:706-14-9
MF:C10H18O2
MW:170.25
EINECS:211-892-8
Product Categories:Cosmetics;Food Additive;lactone flavors
Mol File:706-14-9.mol
gamma-Decalactone Structure
gamma-Decalactone Chemical Properties
Boiling point 281 °C
density 0.948 g/mL at 25 °C (lit.)
vapor pressure 0.72Pa at 25℃
FEMA 2360 | GAMMA-DECALACTONE
refractive index n20/D 1.449
Fp >230 °F
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
form neat
Specific Gravity0.950.948
color Colourless
Odorat 100.00 %. fresh oily waxy peach coconut buttery sweet
Odor Typefruity
optical activity[α]24/D +34°, neat
Water Solubility 1.26g/L at 20℃
JECFA Number231
BRN 117547
InChIKeyIFYYFLINQYPWGJ-UHFFFAOYSA-N
LogP3 at 25℃
CAS DataBase Reference706-14-9(CAS DataBase Reference)
NIST Chemistry Reference2(3H)-Furanone, 5-hexyldihydro-(706-14-9)
EPA Substance Registry System.gamma.-Decalactone (706-14-9)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39-36
WGK Germany 3
RTECS LU4600000
Hazard Note Irritant
TSCA Yes
HS Code 29322090
MSDS Information
ProviderLanguage
5-Hexyldihydro-2(3H)-furanone English
SigmaAldrich English
ACROS English
ALFA English
gamma-Decalactone Usage And Synthesis
Chemical Propertiesγ-Decalactone has a pleasant, fruity, peach-like odor.
Chemical Propertiesclear colourless to pale yellow liquid
Chemical Propertiesgamma-Decalactone is present in a wide variety of foods and is an almost colorless liquid with an intensely fruity odor,reminiscent of peaches. It is used in perfumery for heavy, fruity flower odors and in aroma compositions, particularly peach flavors.
OccurrenceReported found in peach, apricot and strawberry aroma. Also reported in butter, milk, beer, rum, red and white wine, mango, bilberry, plums, prunes, guava, peach, strawberry fruit and cheeses.
Usesγ-Decalactone may be used as an analytical reference standard for the quantification of the analyte in fruit beverages using different chromatography techniques.
DefinitionChEBI: Gamma-decalactone is a gamma-lactone that is oxolan-2-one substituted by a hexyl group at position 5. It has a role as a flavouring agent, a food additive and an anticonvulsant. It is a gamma-lactone and a tetrahydrofuranone.
PreparationNaturalγ-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
Aroma threshold valuesDetection: 1 to 11 ppb
Taste threshold valuesTaste characteristics at 10 ppm: creamy, fatty, oily, buttery sweet, coconut, fruity and peach-like.
Synthesis Reference(s)The Journal of Organic Chemistry, 55, p. 462, 1990 DOI: 10.1021/jo00289a016
Synthetic Communications, 18, p. 2241, 1988 DOI: 10.1080/00397918808082366
General Descriptionγ-Decalactone is a flavor and fragrance compound, which finds applications in food and beverage industry.
Flammability and ExplosibilityNotclassified
SynthesisBy heating γ-bromocapric acid in a sodium carbonate solution; by prolonged heating of 9-decen-1-oic acid with 80% H2SO2 at 90°C
gamma-Decalactone Preparation Products And Raw materials
Raw materialsMalonic acid-->Castor oil-->Undecenoic acid-->Octanal-->5-(6)-Decenoic acids mixture-->9-DECENOIC ACID
Preparation ProductsN,N-Diethyldecanamide-->1-(piperidin-1-yl) decan-1-one
Canrenone Alantolactone 2-Oxetanone Undecan-4-olide Gibberellic acid gamma-Decalactone TRIOXSALEN (-)-Corey lactone diol 4-Hexanolide 4-Aminobutyric acid 5-Decanolide D-(+)-Glucono-1,5-lactone 3-Methyl-1,2-cyclopentanedione PICROTOXIN 4-Heptanolide Isoalantolactone Gamma Butyrolactone GIBBERELLIN A9 METHYL ESTER

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