59812-96-3

Usage

Uses

Used in Fragrance Industry:
(R)-5-HEXADECANOLIDE STANDARD FOR GC is used as a fragrance ingredient for its ability to provide a long-lasting, animalic note in perfumes and personal care products. Its sweet, musky odor adds depth and complexity to the overall scent, making it a valuable addition to the fragrance formulations.
Used in Gas Chromatography Analysis:
(R)-5-HEXADECANOLIDE STANDARD FOR GC is used as a reference compound for testing and calibrating GC systems. Its role in ensuring accurate and reliable results in fragrance analysis and quality control is vital, as it helps to maintain the consistency and integrity of the products being analyzed.
Used in Quality Control:
(R)-5-HEXADECANOLIDE STANDARD FOR GC is used as a quality control measure in the fragrance industry. By using (R)-5-HEXADECANOLIDE STANDARD FOR GC as a standard for GC analysis, manufacturers can ensure that their products meet the desired standards and maintain a consistent level of quality throughout the production process.

Upstream product

• 86233-86-5 Methyl 5-hydroxyhexadecanoate 
• 17049-50-2 n-decyl magnesium bromide 
• 97218-70-7 (S)-4-Oxiranyl-butyric acid tert-butyl ester 
• 116262-03-4 (R)-2-n-undecanylcyclopentanone 
• 103367-39-1 methyl 5(R)-(tetrahydropyranyloxy)hexadecanoate 
• 252955-34-3 (6R)-6-undecyl-5,6-dihydro-2-pyranone 
• 389837-58-5 5-oxohexadecanal 
• 59378-98-2 5-tert-butyl methyl glutarate 
• 143-07-7 lauric acid 
• 103367-30-2 methyl (5S)-5,6-O-isopropylidene-5,6-dihydroxyhexanoate 
• 693-67-4 bromoundecane 
• 86838-53-1 (R)-5-Benzyloxy-hexadecanoic acid 
• 98499-04-8 Undecyllithium 
• 133634-37-4 (-)-(5S)-5,6-Epoxyhexanoate d'ethyle 

Relevant academic research and scientific papers

SYNTHESIS OF OPTICALLY PURE (R)- AND (S)-5-n-HEXADECANOLIDE. A PROPOSED PHEROMONE COMPONENT FROM ORIENTAL HORNET

Optically pure (R)- and (S)-5-n-hexadecanolide have been easily prepared by the reaction between optically active 1-bromo-3-tetrahydropyranyloxytetradecane (5) and lithium α-lithioacetate and the following lactonization. 5 was derived from optically pure 3-hydroxytetradecanoic acid obtained by the method reported before.

5-Formyl-δ-valerolactone: A useful synthon for the chiral synthesis of the vespa Orientalis pheromone and the mosquito oviposition attractant pheromone

A synthetic scheme starting from the reaction between the lithiated N-allyl-N-methyl(bisdimethylamino)phosphoramide anion and the triflate derivative of (R)-(-)- or (S)-(+)-2,3-O-isopropylideneglycerol is described to prepare the key chiral synthon (R)-5- or (S)-5-formyl-δ-valerolactone that leads to the title compounds.

Asymmetric routes to pentadec-1-en-4-ol: Application to the syntheses of aculeatins F and epi-F, (R)- and (S)-5-hexadecanolide and a formal synthesis of solenopsin

A short and simple route to the synthesis of pentadec-1-en-4-ol, an important synthetic building block for the aculeatins F and epi-F, insect pheromone 5-hexadecanolide, solenopsin and various other natural products has been developed via proline-catalyze

Enantioselective synthesis of δ-lactones with lipase-catalyzed resolution and mitsunobu reaction

Both enantiomers of a series of δ-lactones (e.g., δ-decalactone, δ-dodelactone, and d-hexadecalactone) were synthesized stereoselectively by Novozym 435-catalyzed resolution. Furthermore, only (S)-enantiomers of d-lactones were synthesized with a combination of Novozym 435-catalyzed resolution and Mitsunobu reaction. Taylor & Francis Group, LLC.

Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan

By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.

One-pot diastereoselective preparation of α,β-unsaturated-γ-silylated-δ-lactones: Application towards natural compounds

Rearrangement of silylated vinyloxiranes into highly functionalized α-silylated-β,γ-unsaturated aldehydes occurs with total chirality transfer and retention of double bond configuration under Pd(0) catalysis. We show that this reaction is a versatile tool in the field of total stereoselective synthesis: enantiomerically pure lactones are obtained. The pheromone 6-n-undecyltetrahydro-2-pyrone 2 and massoilactone, 5-hydroxy-2-decenoic acid lactone 3, are synthesized. We describe herein a novel highly diastereoselective route to α,β-unsaturated-γ-silylated-δ-substituted-δ-lact ones 1.

Dihydro- and Tetrahydrofuran Building Blocks from 1,4:3,6-Dianhydrohexitols. 2. Synthesis of Acetal, Alcohol, Diol, Epoxide, Hydrocarbon, and Lactone Pheromones

The potential of building blocks 1-3 for synthesis of enantiopure substances is illustrated by their transformation to various insect pheromones featuring functionalities specified in the title.A convenient synthesis of building block 3 from sorbitol is described.

Asymmetric Acetalization: A Simple Method for the Synthesis of Chiral α-Monosubstituted Cyclopentanones

Acetalization of α-monosubstituted cyclopentanones with chiral hydroxy thiols under equilibrating conditions afforded a mixture of acetals in a highly diastereoselective manner, and deacetalization of the product affords optically active α-monosubstituted cyclopentanones.

Asymmetric Synthesis of 5- and 6-Membered Lactones from Cyclic Substrates Bearing a C2-Chiral Auxiliary

Optically active lactones were synthesized by a novel asymmetric synthesis in which enantiotopic groups remote from a prochiral center were effectively discriminated.The cyclic diamide alcohols bearing a C2-chiral auxiliary, (+)--2,2'-diamine (4), were designed and prepared such that the hydroxyl group should attack preferentially at one of the two carbonyl groups.By the catalytic action of trifluoroacetic acid, the substrates 6a,b and 19 were smoothly converted to the lactones 7a (71percent de), 7b (97percent de), and 20 (>99percent de), the configurations of whichwere determined to be R, S, and R, respectively.A naturally occurring pheromone, (R)-(+)-5-hexadecanolide (13), was synthesized optically pure from 7b.Transition-state models for the present asymmetric lactonization were constructed according to the stereoelectronic theory proposed by Deslongchamps.The stability of the models was assessed by MM2 calculation, and the direction of asymmetric induction thus calculated coincided with the experimental results.