730-46-1

Basic information

• Product Name: Hexadeca-1,4-Lactone
• Synonyms: gamma-Hexadecalatone;Hexadeca-1,4-Lactone;2(3H)-Furanone, 5-dodecyldihydro-;HEXADECANO-1,4-LACTONE;4-Hydroxyhexadecanoic acid γ-lactone;4-Hydroxypalmitic acid lactone;5-Dodecyl-4,5-dihydro-2(3H)-furanone;5-Dodecyl-4,5-dihydrofuran-2(3H)-one
• CAS NO: 730-46-1
• Molecular Formula: C16H30O2
• Molecular Weight: 254.4082
• Mol File: 730-46-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 40.7-41.3 °C
• Boiling Point: 349.2°C at 760 mmHg
• Flash Point: 145.4°C
• Appearance: /
• Density: 0.912g/cm³
• Vapor Pressure: 4.78E-05mmHg at 25°C
• Refractive Index: 1.456
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Hexadeca-1,4-Lactone(CAS DataBase Reference)
• NIST Chemistry Reference: Hexadeca-1,4-Lactone(730-46-1)
• EPA Substance Registry System: Hexadeca-1,4-Lactone(730-46-1)

Safety Data

• Hazardous Substances Data: 730-46-1(Hazardous Substances Data)

Usage

Description

Hexadeca-1,4-Lactone is a cyclic ester compound with the molecular formula C14H26O2. It is characterized by the presence of a lactone ring and a long hydrocarbon chain. This organic compound is known for its unique chemical properties and potential applications in various industries.

Uses

Used in Flavor and Fragrance Industry:
Hexadeca-1,4-Lactone is used as a flavoring agent for its characteristic sweet, creamy, and woody odor. It is commonly employed in the formulation of perfumes, colognes, and other fragrance products to provide a rich and complex scent profile.
Used in Cosmetics and Personal Care Products:
Hexadeca-1,4-Lactone is used as a fixative in cosmetics and personal care products to enhance the longevity and stability of fragrances. Its ability to bind with other ingredients helps to maintain the scent and improve the overall performance of these products.
Used in Food Industry:
Hexadeca-1,4-Lactone is used as a flavor enhancer in the food industry, particularly in the production of baked goods, confectionery, and dairy products. Its unique taste profile adds depth and complexity to various food items, enhancing the overall flavor experience.
Used in Pharmaceutical Industry:
Hexadeca-1,4-Lactone has potential applications in the pharmaceutical industry as a precursor for the synthesis of various drugs and active pharmaceutical ingredients. Its unique chemical structure allows for the development of new compounds with therapeutic properties.
Used in Plastics and Polymer Industry:
Hexadeca-1,4-Lactone can be used as a monomer in the synthesis of biodegradable polymers and plastics. Its ability to form strong covalent bonds with other monomers makes it a promising candidate for the development of environmentally friendly materials.

InChI:InChI=1/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-15-13-14-16(17)18-15/h15H,2-14H2,1H3

Upstream product

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• 15890-72-9 laurylmagnesium bromide 
• 373-49-9 cis-9-hexadecenoic acid 
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Relevant articles and documents

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.

Sensory-directed identification of creaminess-enhancing volatiles and semivolatiles in full-fat cream

Aimed at defining the chemical nature of creaminess-related flavor compounds in dairy products on a molecular level, a full-fat cream was analyzed for sensorially active volatiles and semivolatiles by means of activity-guided screening techniques. Application of the aroma extract dilution analysis on an aroma distillate prepared from pasteurized cream (30% fat) revealed δ-decalactone, (Z)-6-dodeceno-γ-lactone, γ-dodecalactone, δ-dodecalactone, and 3-methylindole with by far the highest flavor dilution (FD) factors among the 34 odor-active volatiles identified. Using a complementary approach involving silica column chromatography and fractionated high-vacuum distillation combined with sensory experiments enabled the additional identification of δ-tetradecalactone, δ-hexadecalactone, γ-tetradecalactone, γ-hexadecalactone, and δ-octadecalactone as semivolatile flavor components in the cream fat. Although a series of lactones is present in dairy cream, spiking of cream samples with individual lactones revealed that only the δ-tetradecalactone is able to enhance the typical retronasal creamy flavor of the product when added in amounts above its theshold level of 66 μmol/kg. Rather than contributing to the retronasal aroma of cream, first evidence was found that, particularly, γ- and δ-octadecalactones and γ- and δ-eicosalactones are able to influence the melting behavior of cream in the oral cavity.