3301-94-8

Basic information

• Product Name: delta-Nonalactone
• Synonyms: 5-HYDROXYNONANOIC ACID, LACTONE;5-NONANOLIDE;6-butyltetrahydro-2h-pyran-2-one;DELTA-NONALACTONE;DELTA-NONANOLACTONE;DELTA-PELARGONOLACTONE;D-NONALACTONE;FEMA 3356
• CAS NO: 3301-94-8
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.22
• EINECS: 221-974-5
• Product Categories: Cosmetics
• Mol File: 3301-94-8.mol

Chemical Properties

• Melting Point: -26°C
• Boiling Point: 115-116 °C2 mm Hg(lit.)
• Flash Point: 112 °F
• Appearance: colourless to pale yellow liquid with a coconut-like odour
• Density: 0.893 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.41-0.75Pa at 20-25℃
• Refractive Index: n20/D 1.455(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 114460
• CAS DataBase Reference: delta-Nonalactone(CAS DataBase Reference)
• NIST Chemistry Reference: delta-Nonalactone(3301-94-8)
• EPA Substance Registry System: delta-Nonalactone(3301-94-8)

Safety Data

• Statements: 10
• Safety Statements: 16-24/25
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3301-94-8(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
Delta-Nonalactone is used as a flavoring agent for its creamy, coconut, lactonic, sweet, and dairy-like taste with milky nuances. It is commonly utilized in curry, nut, tomato, tropical, caramel, and dairy flavors.
Used in Fragrance Industry:
In fragrance applications, delta-Nonalactone delivers apricot, butter, grape, passion fruit, plum, tea green, and tobacco notes.
Natural Occurrence:
Delta-Nonalactone is found in various natural sources, including melon, butter, chicken fat, grilled beef, cured pork, pork fat and liver, beer, malt, bourbon whiskey, cognac, rum, white wine, black tea, asparagus, mango, starfruit, mountain papaya, and cooked shrimps. It has also been reported as responsible for the off-flavor in milk fat.

Preparation

By microbiological reduction of the corresponding keto acids; by a patented process

Upstream product

• 3637-15-8 5-oxo-nonanoic acid 
• 934-42-9 2-butylcyclopentanone 
• 98560-11-3 tetrahydro-6-(3-iodopropyl)-2H-pyran-2-one 
• 1489-74-3 cyclooctane-1,5-dione 
• 23418-82-8 cis-1,5-cyclooctanediol 
• 37996-41-1 9-oxabicyclo[3.3.1]nonan-1-ol 
• 589-62-8 octan-4-ol 
• 201230-82-2 carbon monoxide 
• 592-41-6 1-hexene 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 16400-70-7 6-butyl-5,6-dihydro-2H-pyran-2-one 
• 2277-18-1 5-nonenal 
• 143508-30-9 O^ω-<(5S,R)-5-butyl-5-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>pentanoyl>-N^α-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester 
• 137226-81-4 (9S,12S,13R)-2-butyl-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane 
• 137226-80-3 (9S,12S,13R)-2-butyl-12-(cyclohexylmethyl)-13-hydroxy-9-<<(phenylmethoxy)carbonyl>amino>-6,10,14-trioxo-1,5-dioxa-11-azacyclotetradecane 
• 143508-51-4 (1S,R)-1-butyl-5-oxo-5-(phenylmethoxy)pentyl (4S,5R)-4-(cyclohexylmethyl)-2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-5-oxazolidinecarbxylate 
• 143508-50-3 5-Hydroxy-nonanoic acid benzyl ester 
• 310419-98-8 (S)-(+)-5-hydroxy-1-nonanylbenzoate 
• 310419-99-9 (R)-(-)-5-fluoro-1-nonyl-benzoate 

Relevant articles and documents

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.

1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents

The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents

The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

INFANT FORMULA CONTAINING AN AROMA COMPOSITION FOR USE AS FRAGRANCE

The invention relates to a nutraceutical composition such as infant formula or infant food comprising a) a defined aroma composition; b) a methodology for developing, maintaining certain aroma constituents in the infant formula and an aroma or fragrance composition to be used to increase the acceptance of a person or an object by the baby or new born.

New strategies in carbonylation chemistry: The synthesis of δ-lactones from saturated alcohols and CO

This paper describes the δ-carbonylation of saturated alcohols which uses a 1,5-hydrogen-transfer reaction of alkoxyl radicals and subsequent carbonylation at the δ-carbon atoms as the key. The carbonylation reactions of five classes of saturated alcohols, namely, primary alcohols having primary δ-carbons, primary alcohols having secondary δ-carbons, primary alcohols having tertiary δ-carbons, secondary alcohols having primary δ- carbons, secondary alcohols having secondary δ-carbons, were carded out, in which lead tetraacetate (LTA) was used as a one-electron oxidant to generate the alkoxyl radicals. Carbonylation of these saturated alcohols, except for primary alcohols having tertiary δ-carbons, took place to afford δ-lactones in moderate to good yields. The mechanism of the remote carbonylation likely involves (1) alkoxyl radical generation via LTA oxidation of a saturated alcohol, (2) conversion of this alkoxyl radical to a δ-hydroxyalkyl radical by a 1,5-hydrogen-transfer reaction, (3) CO trapping of the δ-hydroxyalkyl radical yielding an acyl radical, and (4) oxidation and cyclization of the acyl radical to give a δ-lactone. A metal salt-free system was also tested for a substrate derived from a tertiary alcohol having a secondary δ- carbon; the photolysis of an alkyl 4-nitrobenzenesulfenate under CO pressures gave a δ-lactone in moderate yield.

Catalytic oxidation of alkyl- and cycloalkylcyclanones into lactones

Pilot-plant syntheses of alkyl and cycloalkylcyclanones and their subsequent liquid-phase oxidation into lactones are described. Characteristics of resulting intermediates and target products are reported.

A NEW ROUTE TO γ-SUBSTITUTED γ-LACTONES AND δ-SUBSTITUTED δ-LACTONES BASED ON THE REGIOSELECTIVE β-SCISSION OF ALKOXY RADICALS GENERATED FROM TRANSANNULAR HEMIACETALS

A new general synthesis of γ-substituted γ-lactones and δ-substituted δ-lactones including dihydro-5-octyl-2(3H)-furanone, a natural pheromone, is described.The synthesis involves the regioselective β-scission of alkoxy radicals generated from transannular hemiacetals as the key step. Key Words: γ-Lactones; δ-Lactones; Mercury(II) Oxide-Iodine Reagent; Photolysis; β-Scission of Alkoxyl Radicals

PHASE TRANSFER CATALYSIS AND HOMOGENEOUS REACTIONS WITH β-OXYALKYL RADICALS FROM ORGANOMERCURIALS

β-Alkoxy- and β-hydroxyalkyl radicals generated by sodium borohydride reduction of oxymercurials react with electron deficient olefins to give addition compounds in a homogeneous process.Heterogeneous reactions are also successful in the presence of catalytic amounts of surfactants and provide a superior method for the "one pot" reductive alkylation of oxymercurials.