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

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

Uses

Used in Food Industry:
Undecanolactone is used as a flavoring agent for various food products such as soft drinks, candy, margarine, ice cream, cold and baked goods, etc., due to its unique and desirable taste and aroma.
Used in Perfumery:
Undecanolactone is used as a fragrance ingredient in the perfumery industry, providing a sweet and creamy scent.
Used in Enzyme Activity Studies:
Undecanoic δ-lactone, a derivative of Undecanolactone, has been used as a substrate to investigate the activities of stimulated and nonstimulated human serum paraoxonase (PON1) samples, contributing to the understanding of enzyme functions and potential medical applications.

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%.

Preparation

By intramolecular Cannizzaro-type rearrangement of 2-hexylglutaraldehyde.

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

• 13686-98-1 undecane-1,5-diol 
• 201230-82-2 carbon monoxide 
• 2051-31-2 4-decanol 
• 13074-65-2 2-hexylcyclopentanone 
• 124-38-9 carbon dioxide 
• 62358-93-4 1-Phenylsulfanyl-decan-4-ol 
• 7664-93-9 sulfuric acid 
• 389837-71-2 5-oxoundecanal 
• 36971-14-9 dec-1-en-4-ol 
• 79-10-7 acrylic acid 
• 401515-97-7 2-pyridylmethyl formate 
• 36633-49-5 1-hydroxy-1-hexyl-cyclopentane 
• 706-14-9 5-hexyldihydro-2(3H)-furanone 
• 111-71-7 heptanal 

Downstream Products

• 139054-22-1 (2R,6R,8S)-4-phenyl-8-n-hexyl-1,5,7-trioxaspiro<5.5>undecane 
• 139054-22-1 (4R,6R,8R)-4-phenyl-8-n-hexyl-1,5,7-trioxaspiro<5.5>undecane 
• 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 

Relevant articles and documents

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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.

Polycyclic ketone monooxygenase from the thermophilic fungus Thermothelomyces thermophila: A structurally distinct biocatalyst for bulky substrates

Regio- and stereoselective Baeyer-Villiger oxidations are difficult to achieve by classical chemical means, particularly when large, functionalized molecules are to be converted. Biocatalysis using flavin-containing Baeyer-Villiger monooxygenases (BVMOs) is a wellestablished tool to address these challenges, but known BVMOs have shortcomings in either stability or substrate selectivity. We characterized a novel BVMO from the thermophilic fungus Thermothelomyces thermophila, determined its three-dimensional structure, and demonstrated its use as a promising biocatalyst. This fungal enzyme displays excellent enantioselectivity, acts on various ketones, and is particularly active on polycyclic molecules. Most notably we observed that the enzyme can perform oxidations on both the A and D ring when converting steroids. These functional properties can be linked to unique structural features, which identify enzymes acting on bulky substrates as a distinct subgroup of the BVMO class.

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.

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.

Oxidation of the cyclopentanone and cyclohexanone alkyl derivatives in a pseudohomogeneous system without a phase transfer agent

The reaction of catalytic oxidation of C5-C12 alkyl- and cycloalkylcyclopentanones and -cyclohexanones to lactones in a pseudohomogeneous system without the participation of phase transfer agents was investigated. It was established that the catalytic systems prepared on the basis of molybdenum and tungsten blue (MeOnBrm, where Me = Mo, W, n = 1, 2, m = 2, 3) and H3PO4 deposited on powdered activated carbon AG-3 at 40-60°C, at 5-6 h duration exhibit a high selectivity in the reaction of nucleophilic addition of oxygen to the ketones with the formation of the valero- and caprolactones. Pleiades Publishing, Ltd., 2011.

Crystal structures of cyclohexanone monooxygenase reveal complex domain movements and a sliding cofactor

Cyclohexanone monooxygenase (CHMO) is a flavoprotein that carries out the archetypical Baeyer-Villiger oxidation of a variety of cyclic ketones into lactones. Using NADPH and O2 as cosubstrates, the enzyme inserts one atom of oxygen into the substrate in a complex catalytic mechanism that involves the formation of a flavin-peroxide and Criegee intermediate. We present here the atomic structures of CHMO from an environmental Rhodococcus strain bound with FAD and NADP+ in two distinct states, to resolutions of 2.3 and 2.2 A. The two conformations reveal domain shifts around multiple linkers and loop movements, involving conserved arginine 329 and tryptophan 492, which effect a translation of the nicotinamide resulting in a sliding cofactor. Consequently, the cofactor is ideally situated and subsequently repositioned during the catalytic cycle to first reduce the flavin and later stabilize formation of the Criegee intermediate. Concurrent movements of a loop adjacent to the active site demonstrate how this protein can effect large changes in the size and shape of the substrate binding pocket to accommodate a diverse range of substrates. Finally, the previously identified BVMO signature sequence is highlighted for its role in coordinating domain movements. Taken together, these structures provide mechanistic insights into CHMO-catalyzed Baeyer-Villiger oxidation.

Investigations of the scope and mechanism of the tandem hydroesterification/lactonization reaction

(Chemical Equation Presented) Heating allylic and homoallylic alcohols and 2-pyridylmethyl formate in the presence of Ru3(CO)12 initiates a tandem sequence of hydroesterification and lactonization. Mechanistic studies suggest that regioselectivity and overall reaction efficiency are governed by the relative rates of reductive elimination and β-hydride elimination for the alkylruthenium intermediates.

Tandem cross-metathesis/hydrogenation/cyclization reactions by using compatible catalysts

(Matrix presented) A one-pot tandem cross-metathesis/hydrogenation/cyclization procedure was achieved at room temperature, under 1 atm of hydrogen, in the presence of a ruthenium catalyst and PtO2 showing the compatibility of the two catalysts. This tandem reaction allows the synthesis of substituted lactones and lactols from acrylic acid and acrolein, respectively, in the presence of unsaturated alcohols.

Compounds having protected hydroxy groups

The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.