713-95-1

Basic information

• Product Name: delta-Dodecalactone
• Synonyms: 2H-Pyran-2-one, tetrahydro-6-heptyl;5-Hydroxydodecanoic acid, lactone;5-hydroxy-dodecanoicacidelta-lactone;5-hydroxydodecanoicacidlactone;6-heptyltetrahydro-2h-pyran-2-on;beta-Dodecalactone;Dodecan-5-olide;Dodecanoic acid, 5-hydroxy-, delta-lactone
• CAS NO: 713-95-1
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.3
• EINECS: 211-932-4
• Product Categories: Cosmetics;Food Additive
• Mol File: 713-95-1.mol
• Article Data: 21

Chemical Properties

• Melting Point: −12 °C(lit.)
• Boiling Point: 140-141 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless liquid with peach fruit flavor
• Density: 0.942 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00155mmHg at 25°C
• Refractive Index: n20/D 1.460(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.001[at 20 ℃]
• Water Solubility: Not miscible or difficult to mix in water.
• BRN: 1282749
• CAS DataBase Reference: delta-Dodecalactone(CAS DataBase Reference)
• NIST Chemistry Reference: delta-Dodecalactone(713-95-1)
• EPA Substance Registry System: delta-Dodecalactone(713-95-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 2
• RTECS: UQ0850000
• TSCA: Yes
• Hazardous Substances Data: 713-95-1(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
Delta-Dodecalactone is used as a flavoring agent for its distinctive peach-like aroma, adding a natural and appealing scent to various food products and beverages.
Used in Daily Chemical Essence:
In the daily chemical industry, delta-Dodecalactone serves as an essential component in the formulation of perfumes, cosmetics, and personal care products, enhancing their fragrance and sensory experience.
Used in Agrochemical Industry:
Delta-Dodecalactone is utilized in the agrochemical field, where it plays a role in the development of pest control agents and other agricultural products, potentially improving crop yields and protection.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, delta-Dodecalactone is employed as an ingredient in the development of drugs and medicinal products, possibly due to its unique properties and potential therapeutic effects.
Used in Dye and Pigment Industry:
Delta-Dodecalactone is also used in the dyestuff field, where it contributes to the production of dyes and pigments, enhancing their color and performance in various applications.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 1159, 1984 DOI: 10.1016/S0040-4039(01)91549-7

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

Taste at 10 ppm

InChI:InChI=1/C12H22O2/c1-2-3-4-5-6-8-11-9-7-10-12(13)14-11/h11H,2-10H2,1H3

Upstream product

• 137-03-1 2-heptylcyclopentanone 
• 89110-85-0 1-undecyn-5-ol 
• 3637-16-9 5-oxododecanoic acid 
• 89110-90-7 2-heptyl-oxetane 
• 134852-90-7 2-butyl-3,3-(1'-heptyl)tetrameethyleneoxaziridine 
• 91420-50-7 t-butyl 5-hydroxyundecanoate 

Downstream Products

• 111-87-5 octanol 
• 124-13-0 Octanal 
• 10522-37-9 undec-3-en-2-one 
• 65899-18-5 4-hydroxyundecan-2-one 
• 25826-10-2 undecane-2,4-dione 
• 848084-10-6 C₂₅H₃₅N₅O₆S 
• 7779-95-5 5-hydroxydodecanoic acid 
• 57084-18-1 gamma-dodecalactone 
• 16400-72-9 δ-heptyl-Δ^α,β-pentenolide 

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.

3D-Network porous polymer bonded metalloporphyrin: An efficient and reusable catalyst for the Baeyer-Villiger oxidation

A new, green catalyst was prepared through immobilization of metalloporphyrin on the surface of 3D-network polymer based on calix[4]resorcinarene (PC4RA), which efficiently catalyze B-V oxidation reaction using O2/benzaldehyde. The catalyst demonstrated excellent activity, which is highly potential for cyclic aliphatic ketones oxidation under mild conditions. IR spectroscopy, UV-Vis spectroscopy, thermal gravimetric analysis, energy dispersive spectroscopy and scanning electron microscopy are some of the spectroscopic methods used to characterize the new synthesized solid support.

Synthesis, antibacterial activities, and sustained perfume release properties of optically active5-hydroxy- And 5-acetoxyalkanethioamide analogues

5-Acetoxy- and 5-hydroxyalkanethioamide analogues showed high antibacterial activity against Staphylococcus aureus. Antibacterial thioamides were prepared from 5-alkyl-δ-lactones by amidation, thionation, and subsequent deacetylation. Optically active thioamides with 99% diastereomeric excesses were prepared by diastereomeric resolution using Cbz-L-proline as the resolving agent. Antibacterial thioamides were slowly lactonized by a lipase catalyst. Therefore, these thioamides are potential sustained-release perfume compounds having antibacterial properties.

Synthesis method of deltalactone

The invention discloses a synthesis method of deltalactone. The synthesis method is characterized by comprising the following steps: taking 5-oxo fatty acid as a starting raw material, and reacting under hydrogen pressure of 5atm to 30atm and at 120 DEG C to 180 DEG C in the presence of catalysts including Ru/C and the like; firstly, carrying out a hydrogenation reaction of carbonyl to obtain an intermediate product 5-hydroxyl fatty acid M1; meanwhile, carrying out intramolecular dehydration and esterification on M1 and carrying out a one-pot reaction to generate the deltalactone. A specific reaction formula is shown in the description, wherein R=CH3(CH2)n- and n is equal to 1 to 8.

Catalytic oxidation method to synthesize lactone compound with cyclic ketones

The invention discloses a method for synthesizing a lactone compound through catalytic oxidation of cyclic ketone. The method is characterized by using a transition metal oxide as a catalyst, a hydrogen peroxide solution as an oxidizing reagent and acetonitrile as a solvent to catalytically oxidize cyclic ketone to synthesize the lactone compound, wherein the transition metal oxide is selected from any one of TiO2, Fe2O3, Co3O4, ZrO2 and WO3. The method has the obvious advantages that the conversion rate of cyclic ketone and atom utilization of reaction are increased by adopting the transition metal oxide as the catalyst; the used transition metal oxide catalyst can be reused; waste acid treatment and strong acid corrosivity are avoided, energy is saved, emission is reduced, and the safety is high; the cleanliness and safety of industrial preparation reaction are improved and the environmental pollution is reduced by applying the hydrogen peroxide solution as the oxidizing reagent.

Baeyer-villiger oxidation of cyclic ketones using aqueous hydrogen peroxide catalyzed by potassium salts of tungstophosphoric acid

The salts of 12-tungstophosphoric acid catalysts are prepared with varying potassium content. The resulting catalysts are active for the Baeyer-Villiger oxidation of cyclic ketones with 30 wt% H2O2 and achieve good conversions and yields. KHPW is the preferred catalyst in the reaction because of its reusability and environmental benefits.

PROCESS FOR THE OXIDATION OF ORGANIC CARBONYL COMPOUNDS

A process for the oxidation of an organic carbonyl compound comprising reacting the organic carbonyl compound, optionally in the presence of a solvent, with hydrogen peroxide in the presence of a catalyst comprising a tin-containing zeolitic material having an MWW-type framework structure.

Process for the Oxidation of Organic Carbonyl Compounds

A process for the oxidation of an organic carbonyl compound comprising reacting the organic carbonyl compound, optionally in the presence of a solvent, with hydrogen peroxide in the presence of a catalyst comprising a tin-containing zeolitic material having an MWW-type framework structure.

METHOD FOR MANUFACTURING ESTER

The present invention relates to a method for manufacturing an ester from a ketone or an aldehyde, which is a reactive substrate, by a Baeyer-Villiger oxidation reaction using hydrogen peroxide, and in this method, as a catalyst, M(BAr4)n, which is a metal borate, is used (M represents an alkali metal or an alkaline earth metal; Ar represents an aryl; and n is the same number as the valence of M). For example, when cyclohexanone was used as the reactive substrate, and Sr[B(3,5-CF3C6H3)4]2 was used as the catalyst, ε-caprolactone was obtained at an isolated yield of 82%.

Cascade biotransformations via enantioselective reduction, oxidation, and hydrolysis: Preparation of (R)-δ-lactones from 2-alkylidenecyclopentanones

The first cascade biotransformation involving enantioselective reduction of a C=C double bond, Baeyer-Villiger oxidation, and lactone hydrolysis was developed as a green and sustainable tool for synthesizing enantiopure δ-lactones. One-pot cascade biotransformations were achieved with Acinetobacter sp. RS1 containing a novel enantioselective reductase and an enantioselective lactone hydrolase and Escherichia coli coexpressing cyclohexanone monooxygenase and glucose dehydrogenase, converting easily available 2-alkylidenecyclopentanones 1-2 into the corresponding valuable flavors and fragrances (R)-δ-lactones 5-6 in high ee. The one-pot synthesis is better than the reported two-step preparation. This concept is useful in developing other redox cascades with the substrates containing C=C double bond.