gamma-Nonanolactone

gamma-Nonanolactone Basic information
Description Reference
Product Name:gamma-Nonanolactone
Synonyms:G-NONALACTONE;FEMA 2781;GAMMA-NONALACTONE;GAMMA-NONANOIC LACTONE;GAMMA-NONANOLACTONE;GAMMA-PELARGONOLACTONE;δ-n-Amylbutyrolactone;ALDEHYDE C-18
CAS:104-61-0
MF:C9H16O2
MW:156.22
EINECS:203-219-1
Product Categories:lactone flavors;Carbonyl Compounds;Lactones;Organic Building Blocks;Cosmetics;Food Additive
Mol File:104-61-0.mol
gamma-Nonanolactone Structure
gamma-Nonanolactone Chemical Properties
Boiling point 121-122 °C6 mm Hg(lit.)
density 0.976 g/mL at 25 °C(lit.)
vapor pressure 1.9Pa at 25℃
FEMA 2781 | GAMMA-NONALACTONE
refractive index n20/D 1.447(lit.)
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Sparingly), Hexanes (Slightly)
form neat
color Colourless
Odorat 100.00 %. coconut creamy waxy sweet buttery oily
Odor Typecoconut
Water Solubility 9.22g/L(25 ºC)
JECFA Number229
Stability:Hygroscopic
LogP2.5 at 25℃
CAS DataBase Reference104-61-0(CAS DataBase Reference)
NIST Chemistry Reference2(3H)-Furanone, dihydro-5-pentyl-(104-61-0)
EPA Substance Registry SystemDihydro-5-pentyl-2(3H)-furanone (104-61-0)
Safety Information
Safety Statements 24/25-22
WGK Germany 1
RTECS LU3675000
HS Code 29322090
Hazardous Substances Data104-61-0(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
gamma-Nonanolactone Usage And Synthesis
DescriptionGamma-Nonalactone (5-Pentyloxolan-2-one) is a colorless to pale yellow clear oily liquid. It is found in bourbon whiskey, black currant berries, melon, papaya, pineapple, fresh blackberry, etc.1,2 It has a creamy and coconut-like odor.3 It is used as a flavoring agent in food to give coconut flavor. It is also a potential multi-species attractant lure for grain beetle pests.4
Reference
  1. https://en.wikipedia.org/wiki/Gamma-Nonalactone
  2. George A. Burdock, Encyclopedia of Food and Color Additives, Band 1, 1996, ISBN 0-8493-9416-3
  3. http://www.thegoodscentscompany.com
  4. https://www.sigmaaldrich.com
Descriptionγ-Nonalactone has a strong odor reminiscent of coconut and a fatty, peculiar taste. May be synthesized by reacting methylacry- late and hexanol in the presence of ditertiarybutyl peroxide; by condensation of undecylenic acid and malonic acid; by lactonizα- tion of nonenoic acid.
Chemical Propertiesγ-Nonalactone has a strong odor reminiscent of coconut and a fatty, peculiar taste.
Chemical Propertiesgamma-Nonanolactone occurs in many foods and is a pale yellow liquidwith a coconut-like aroma. It has numerous applications, similarly to those of ??-octalactone, in aroma compositions and perfumery.
OccurrenceReported found in peaches, apricots, roasted barely, rum, tomato, currants, guava, raisin, papaya, peach, pineapple, blackberry, strawberry jam, asparagus, wheat and crispbread, Camembert cheese, butter, milk, chicken, beef, lamb and pork fat, cooked beef and pork, beer, cognac, whiskies, sherry, grape wines, cocoa, green tea, pecan, oats, soybean, avocado, passion fruit, plum, plumcot, beans, mushroom, starfruit, fenugreek, mango, tamarind, rice, prickly pear, buckwheat, licorice, malt, wort, cherimoya, Bourbon vanilla, shrimp, nectarine, maté and sweet grass oil.
Uses(γ-Nonalactone is one of the prominent, odour active compounds present in freshly cooked rice, and also has a coconut-like scent. γ-Nonalactone is also present in aging beers and other fermenting products.
UsesIn flavor applications, this compound contributes to caramel notes. In fragrance applications, this compound contributes is used in amber, balsam, floral, juniper berry, nutmeg, pine, coconut, maple and oriental notes.
Uses(Gamma)-Nonalactone is a synthetic flavoring agent that is a colorless to yellow liquid of strong, coconut-like odor. It is soluble in most fixed oils, mineral oil, and propylene glycol. It is stable in acids and unstable in alkali and should be stored in glass, tin, or aluminum containers. It is used in coconut flavors and has application in gelatins, puddings, baked goods, candy, and ice cream at 11–55 ppm. It is also termed aldehyde c-18.
PreparationBy reacting methylacrylate and hexanol in the presence of ditertiarybutyl peroxide; by condensation of undecylenic acid and malonic acid by lactonization of nonenoic acid
Aroma threshold valuesDetection: 7 ppb
Taste threshold valuesTaste characteristics at 10 ppm: coconut, creamy, waxy with fatty milky notes
General Descriptionγ-Nonanoic lactone is an oak lactone commonly found in wines aged in oak barrels. It is the main flavor component of coconut. γ-Nonanoic lactone is also a potential multi-species attractant lure for grain beetle pests.
Flammability and ExplosibilityNonflammable
Safety ProfileModerately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.
gamma-Nonanolactone Preparation Products And Raw materials
Raw materialsTriethylamine-->Methyl acrylate-->Malonic acid-->Heptaldehyde-->1-Hexanol-->Manganese triacetate dihydrate-->Y type molecular sieve-->1-HEPTENE-->nonenoic acid
BETA-BUTYROLACTONE Canrenone 2-Oxetanone gamma-Decalactone TRIOXSALEN 4-Hexanolide Cyclopentanecarbaldehyde 4-Aminobutyric acid 2-Chlorophenyl cyclopentyl ketone CYCLOPENTYLMAGNESIUM CHLORIDE gamma-Octanoic lactone delta-Dodecalactone TETRAPENTYLAMMONIUM BROMIDE gamma-Nonanolactone TERT-AMYL METHYL ETHER Undecanolactone Gamma Butyrolactone Spironolactone

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