gamma-nonanoic lactone
gamma-nonanoic lactone
CAS: 104-61-0
Molecular Formula: C9H16O2
gamma-nonanoic lactone - Names and Identifiers
| Name | gamma-nonanoic lactone |
| Synonyms | FEMA 2781 Aldehyde c18 Nonanolactone _-Nonalactone G-NONALACTONE nonan-4-olide ALDEHYDE C-18 COCOUNT ALDEHYDE GAMMA-NONALACTONE Gamma-Nonalactone Nonalactone, gama- GAMMA-NONANOLACTONE gamma-Nonanolactone δ-n-Amylbutyrolactone GAMMA-NONANOIC LACTONE GAMMA-PELARGONOLACTONE gamma-nonanoic lactone 5-pentyldihydrofuran-2(3H)-one (5S)-5-pentyldihydrofuran-2(3H)-one 4-Hydroxynonanoic acid gamma-lactone |
| CAS | 104-61-0 |
| EINECS | 203-219-1 |
| InChI | InChI=1/C9H16O2/c1-2-3-4-5-8-6-7-9(10)11-8/h8H,2-7H2,1H3/t8-/m0/s1 |
gamma-nonanoic lactone - Physico-chemical Properties
| Molecular Formula | C9H16O2 |
| Molar Mass | 156.22 |
| Density | 0.976g/mLat 25°C(lit.) |
| Melting Point | 98.8℃ |
| Boling Point | 121-122°C6mm Hg(lit.) |
| Flash Point | >230°F |
| JECFA Number | 229 |
| Water Solubility | 9.22g/L(25 ºC) |
| Solubility | Chloroform (Sparingly), Hexanes (Slightly) |
| Vapor Presure | 1.9Pa at 25℃ |
| Appearance | Liquid |
| Color | Colourless |
| Storage Condition | Sealed in dry,Room Temperature |
| Stability | Hygroscopic |
| Refractive Index | n20/D 1.447(lit.) |
| MDL | MFCD00005403 |
| Physical and Chemical Properties | Colorless or light yellow liquid. With coconut-type aroma, a slight fennel sound, diluted apricot, plum aroma. |
| Use | For the deployment of food flavor, feed flavor, etc |
gamma-nonanoic lactone - Risk and Safety
| Safety Description | S24/25 - Avoid contact with skin and eyes. S22 - Do not breathe dust. |
| WGK Germany | 1 |
| RTECS | LU3675000 |
| HS Code | 29322090 |
gamma-nonanoic lactone - Upstream Downstream Industry
| Raw Materials | methylacrylate |
gamma-nonanoic lactone - Nature
Open Data Verified Data
colorless liquid with strong coconut aroma. Soluble in ethanol, propylene glycol, ether and most non-volatile solvents, insoluble in water and glycerol.
Last Update：2024-01-02 23:10:35
gamma-nonanoic lactone - Preparation Method
Open Data Verified Data
nonenoic acid was prepared by the reaction of heptanal with malonic acid, followed by internal esterification, extraction, washing and distillation.
Last Update：2022-01-01 10:07:53
gamma-nonanoic lactone - Use
Open Data Verified Data
It is used as the main flavor of coconut essence, and is also used to blend cream, almond, peach, cherry, nut, tropical fruit and other essences. In baked food, the dosage was 5 5 mg/kg; In candy, 3 3 mg/kg; In pudding, 28 mg/kg; In chewing gum, 15 mg/kg; 14 mg/kg in cold drinks; llmg/kg in soft drinks.
Last Update：2022-01-01 10:07:52
gamma-nonanoic lactone - Reference Information
| FEMA | 2781 | GAMMA-NONALACTONE |
| LogP | 2.5 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Overview | Coconut aldehyde, also known as γ-nonanolactone, γ-Nonanoic lactone, and n-amyl butyrolactone, is colorless or slightly yellow transparent oily liquid, has a sweet coconut aroma, and has a peach and apricot flavor when diluted. Natural products are found in peaches, apricots, tomatoes, rum and fried barley. The reaction of heptanal and malonic acid is used to form nonenoic acid, which is then added with 85% sulfuric acid and stirred, and is obtained by distillation under reduced pressure after washing. It is used to prepare coconut, peach, apricot and other edible flavors, as well as gardenia, moonflower and other makeup and soap flavors. |
| preparation method | 1. using heptanal and malonic acid as raw materials, in the presence of pyridine, condensation to generate hydroxyheptyl malonic acid, further heating and dehydration to generate nonene acid, with (85%) sulfuric acid as lactulant. Heating and cyclization can produce coconut aldehyde. The reaction formula is as follows: 2.1-hexanol and acrylic acid as raw materials, condensation, can be prepared. 3. Methyl acrylate and hexanol as raw materials, in the presence of di-tert-butyl peroxide, reaction, can be prepared. |
| use | used as a spice to prepare fruit flavor flavors such as peach, apricot, plum, strawberry, etc. for food and tobacco. GB2760- 1996 in China stipulates that it is allowed to be used as an edible flavor. It can also be prepared with tuberose jade, jasmine, gardenia and other flower flavor and oriental flavor for cosmetics and soap. (2015-11-17) γ-nonolactone is a food spice temporarily allowed to be used according to the hygienic standard for the use of food additives in China. It is mainly used to prepare flavor flavors such as peach, cherry, coconut, almond, milk, milk fat, etc. The amount used in baked food is 55 mg/kg; 33 mg/kg in candy; 28 mg/kg in pudding; 15 mg/kg in chewing gum; 14 mg/kg in cold drinks; 11 mg/kg in soft drinks. this product is used to prepare fruit flavor beverage essence, such as coconut essence, bitter almond essence, etc., and is also used as a spice for advanced cosmetics. It is also a raw material for organic synthesis. used to mix food essence, feed essence, etc. |
| Production method | 1. It is prepared by the internal esterification of β,γ-nonenoic acid under the action of sulfuric acid. Nonenoic acid is prepared by the reaction of heptanal and malonic acid. Stir the 80% sulfuric acid and nonenoic acid together. After the internal esterification reaction is completed, wash the reactants with water, neutralize the oil layer with sodium carbonate solution, and then wash with water to distill the oil under reduced pressure to obtain γ-Nonenolactone. 2. It is obtained by co-thermal dehydration of 7-hydroxyn-nonanoic acid and sulfuric acid. 3. Using high-valent acetate such as cerium and vanadium or manganese acetate (3) as the oxidant, it is obtained by the reaction of α-heptene and acetic acid. γ nonolactone naturally exists in tomatoes, rum, peaches, barley, But industrially made from malonic acid and heptanal. 70g triethylamine and 52g(0.5 mo1) malonic acid were added into a 500mL flask, stirred slowly to dissolve it, and 57g(0.5 mo1) of newly distilled heptanal were added dropwise within 30min at 40~50 ℃. Then continue to stir the reaction at 75~85 ℃ for 1h until no CO2 gas is released. After cooling, 180mL of 20% hydrochloric acid was added, and the water layer was extracted twice with 50mL benzene. Combine benzene extract and organic layer, wash with water to neutral and then dry with anhydrous sodium sulfate. Benzene is recovered by atmospheric distillation, and the fraction at 130~135 ℃(666.5Pa) is collected as nonenoic acid with refractive index nD201.446 ~ 1.447 and yield of about 75%. 32.2g of nonenoic acid (0.2mol) and 4g of HY molecular sieve were placed in a 250mL flask, stirred at 170 ℃ for 3h, cooled, filtered out the molecular sieve, distilled under reduced pressure, and collected the fraction at 123~128 ℃(800Pa), which is γ-nonolactone. Sulfuric acid can also be 80% as a lactating agent, washed with water after the reaction, neutralized with sodium carbonate solution, washed with water, and finally distilled under reduced pressure to obtain the finished product. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:09
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Raw Materials for gamma-nonanoic lactone