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
• Article Data: 9

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

Description

Hydroxynonanoic acid, δ-lactone has a mild, nut-like odor and a fatty, milk-creamy taste. May be prepared by microbiological reduction of the corresponding keto acids, by a patented process.

Chemical Properties

Hydroxynonanoic acid, δ-lactone has a mild, nut-like odor and a fatty, milk-creamy taste

Occurrence

Reported as responsible for the off-flavor in milk fat. Also found in melon, butter, chicken fat, grilled beef, cured pork, pork fat and liver, beer, malt and bourbon whiskey, cognac, rum, white wine, black tea, asparagus, mango, starfruit, mountain papaya and cooked shrimps

Uses

Suggested uses are in curry, nut, tomato, tropical, caramel and dairy flavors. In fragrance applications, this compound delivers apricot, butter, grape, passion fruit, plum, tea green and tobacco notes.

Preparation

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

Taste threshold values

Taste characteristics at 10 ppm: creamy, coconut, lactonic, sweet and dairy-like with milky nuances.

Upstream product

• 934-42-9 2-butylcyclopentanone 
• 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 
• 98560-11-3 tetrahydro-6-(3-iodopropyl)-2H-pyran-2-one 
• 589-62-8 octan-4-ol 
• 201230-82-2 carbon monoxide 
• 592-41-6 1-hexene 
• 292638-85-8 acrylic acid methyl ester 
• 3637-15-8 5-oxo-nonanoic acid 

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.

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.

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.