710-04-3

Basic information

• Product Name: Undecanolactone
• Synonyms: 2H-Pyran-2-one, 6-hexyltetrahydro-;2H-Pyran-2-one, tetrahydro-3-hexyl-;5-Hydroxyundecanoic acid lactone;5-hydroxy-undecanoicacidelta-lactone;5-hydroxyundecanoicacidlactone;6-hexyltetrahydro-2h-pyran-2-on;beta-Undecalactone;delta-Hexyl-delta-valerolactone
• CAS NO: 710-04-3
• Molecular Formula: C₁₁H₂₀O₂
• Molecular Weight: 184.28
• EINECS: 211-915-1
• Product Categories: Carbonyl Compounds;Lactones;Organic Building Blocks
• Mol File: 710-04-3.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 152-155 °C10.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: colorless liquid
• Density: 0.969 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0019mmHg at 25°C
• Refractive Index: n20/D 1.459(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water
• CAS DataBase Reference: Undecanolactone(CAS DataBase Reference)
• NIST Chemistry Reference: Undecanolactone(710-04-3)
• EPA Substance Registry System: Undecanolactone(710-04-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 2
• RTECS: UQ1320000
• Hazardous Substances Data: 710-04-3(Hazardous Substances Data)

Usage

Synthesis

In a 500ml three-necked flask equipped with a stirrer, dropping funnel and thermometer, add 140ml formic acid and 56g urea-peroxide adduct, stir and dissolve. 28 g (0.17 mol) of 2-hexylcyclopentanone was added dropwise at room temperature, and the dropwise addition was completed in about 1 hour. 168 ml of water was added, and the layers were stirred and separated. The aqueous layer was extracted three times with 28 ml of toluene, and the organic lookchem layers were combined. The toluene in the organic layer was distilled off under reduced pressure, and the temperature was controlled not to exceed 70° C. The residue was the crude product of butyl-undecalactone with a purity of 85% and a yield of 96%. The crude product was distilled with a vacuum thin film distillation device, at 128° C/1.4 kPa, and the distilled product was butyl-undecalactone,? purity 98% ,yield 84%.

Description

Undecanolactone has a sweet, fruity, milky, creamy, buttery, estery, waxy, coconut aroma and taste. It is the key ingredient for the special flavor of natural cream and can be used for flavoring soft drinks, candy, margarine, ice cream, cold and baked goods, etc.

Chemical Properties

Different sources of media describe the Chemical Properties of 710-04-3 differently. You can refer to the following data:
1. Colorless to light-yellow liquid; peachlike odor. Soluble in 4–5 volumes of 60% alcohol; soluble in benzyl alcohol, benzyl benzoate, and most fixed oils. Combustible.
2. Δ-Undecalactone has a creamy, peach-like aroma.

Occurrence

Reported found in coconut flavor, melon, blackberry, blueberry, heated butter, milk, milk powder, cream, coconut meat and starfruit.

Uses

Different sources of media describe the Uses of 710-04-3 differently. You can refer to the following data:
1. Undecanoic δ-lactone has been used as substrate to investigate the activities of stimulated and nonstimulated human serum paraoxonase (PON1) samples.
2. Perfumery, flavoring agent.

Preparation

By intramolecular Cannizzaro-type rearrangement of 2-hexylglutaraldehyde.

Taste threshold values

Taste characteristics at 10 ppm: creamy, coconut, milky, creamy, lactonic and butter fat with a waxy, fruity nuance.

General Description

Undecanoic δ-lactone has been found to be best substarte for good substrates for lactonase from Sulfolobus islandicus (SisLac).

Biochem/physiol Actions

Taste at 10 ppm

InChI:InChI=1/C11H20O2/c1-2-3-4-5-7-10-8-6-9-11(12)13-10/h10H,2-9H2,1H3

Upstream product

• 201230-82-2 carbon monoxide 
• 2051-31-2 4-decanol 
• 389837-71-2 5-oxoundecanal 
• 36971-14-9 dec-1-en-4-ol 
• 401515-97-7 2-pyridylmethyl formate 
• 1453171-91-9 5-hydroxy-1-(pyrrolidin-1-yl)undecan-1-one 
• 1453172-03-6 5-(tert-butyldimethylsilyloxy)-1-(pyrrolidin-1-yl)undecan-1-one 
• 112-38-9 10-undecenoic acid 
• 111-71-7 heptanal 
• 706-14-9 5-hexyldihydro-2(3H)-furanone 
• 120-92-3 cyclopentanone 
• 36633-49-5 1-hydroxy-1-hexyl-cyclopentane 
• 4291-99-0 1-n-hexyl-1-cyclopentene 
• 79-10-7 acrylic acid 

Downstream Products

• 25235-82-9 5-Hydroxyundecansaeure 
• 128372-43-0 trans-7-hexyl-2-phenyl-3-(triethylsiloxy)oxepane 
• 128372-43-0 cis-7-hexyl-2-phenyl-3-(triethylsiloxy)oxepane 
• 132834-90-3 7-hexyl-3-(methylsulphonyloxy)-2-phenylsulphonyloxepane 
• 132834-89-0 3-(t-butyldimethylsiloxy)-7-hexyl-2-phenylsulphonyloxepane 
• 132834-96-9 1-diazo-1-phenylsulphonyl-6-trimethylsiloxydodecan-2-one 
• 128372-41-8 7-hexyl-2-phenylsulphonyl-3-(triethylsiloxy)oxepane 
• 132834-88-9 7-hexyl-2-phenylsulphonyl-3-(trimethylsiloxy)oxepane 
• 132835-04-2 3-acetoxy-7-hexyl-2-phenylsulphonyloxepane 
• 132835-05-3 7-hexyl-3-(methoxymethoxy)-2-phenylsulphonyloxepane 
• 128372-34-9 1-diazo-6-hydroxy-1-phenylsulphonyldodecan-2-one 
• 128372-45-2 7-hexyl-2-(3-phenylpropenylidene)oxepane-3-one 
• 128699-21-8 7-hexyl-2-phenylsulphonyloxepan-3-one 
• 132834-87-8 7-hexyl-2-phenylsulphonyloxepan-3-ol 

Relevant articles and documents

Genome Mining of Oxidation Modules in trans-Acyltransferase Polyketide Synthases Reveals a Culturable Source for Lobatamides

Bacterial trans-acyltransferase polyketide synthases (trans-AT PKSs) are multimodular megaenzymes that biosynthesize many bioactive natural products. They contain a remarkable range of domains and module types that introduce different substituents into growing polyketide chains. As one such modification, we recently reported Baeyer–Villiger-type oxygen insertion into nascent polyketide backbones, thereby generating malonyl thioester intermediates. In this work, genome mining focusing on architecturally diverse oxidation modules in trans-AT PKSs led us to the culturable plant symbiont Gynuella sunshinyii, which harbors two distinct modules in one orphan PKS. The PKS product was revealed to be lobatamide A, a potent cytotoxin previously only known from a marine tunicate. Biochemical studies show that one module generates glycolyl thioester intermediates, while the other is proposed to be involved in oxime formation. The data suggest varied roles of oxygenation modules in the biosynthesis of polyketide scaffolds and support the importance of trans-AT PKSs in the specialized metabolism of symbiotic bacteria.

Direct room-temperature lactonisation of alcohols and ethers onto amides: An "amide strategy" for synthesis

Last-minute deal: A direct lactonisation of ethers and alcohols onto amides that proceeds at room temperature under mild conditions is reported (see scheme). This allows the effective saving of up to two unproductive, sequential deprotection operations in synthetic sequences. Mechanistic studies are described, and a new "amide strategy" that exploits the dual robustness/late-stage selective activation properties of this functional group is outlined. Copyright

Tandem isomerization-lactonization of olefinic fatty acids using the Lewis acidic ionic liquid, choline chloride·2ZnCl2

The tandem isomerization-lactonization of unsaturated fatty acids to their corresponding γ-lactones was carried out for the first time in the presence of a Lewis acidic ionic liquid, choline chloride·2ZnCl 2. The ionic liquid initially catalyzes the stepwise migration of the double bond along the carbon chain toward the carboxyl group at the Δ4 position, which subsequently undergoes lactonization resulting in the formation of γ-lactones. This one step process allows the formation of γ-lactone in good yield with little or no formation of δ-lactones. The studied ionic liquid plays the dual role of solvent as well as catalyst.