Oxacyclohexadecan-2-one

Base Information

• Chemical Name: Oxacyclohexadecan-2-one
• CAS No.: 106-02-5
• Deprecated CAS: 81031-90-5
• Molecular Formula: C15H28O2
• Molecular Weight: 240.386
• Hs Code.: 29322090
• European Community (EC) Number: 203-354-6
• NSC Number: 36763
• UNII: OK17S3S98K
• DSSTox Substance ID: DTXSID6044359
• Nikkaji Number: J4.546B
• Wikipedia: Cyclopentadecanolide
• Wikidata: Q9251595
• NCI Thesaurus Code: C77485
• RXCUI: 1312715
• Metabolomics Workbench ID: 46558
• ChEMBL ID: CHEMBL3560504
• Mol file: 106-02-5.mol

Synonyms:exaltolide;thibetolide

Chemical Property of Oxacyclohexadecan-2-one

Chemical Property:

• Appearance/Colour: white crystalline low melting solid
• Vapor Pressure: 6.18E-06mmHg at 25°C
• Melting Point: 34-38 °C(lit.)
• Refractive Index: 1.4700
• Boiling Point: 344.797 °C at 760 mmHg
• Flash Point: 143.392 °C
• PSA: 26.30000
• Density: 0.885 g/cm³
• LogP: 4.61450
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, Ethyl Acetate, Methanol (Slightly)
• Water Solubility.: Soluble in alcohol, dipropylene glycol. Insoluble in water.
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 240.208930132
• Heavy Atom Count: 17
• Complexity: 189

Purity/Quality:

99.9% ^*data from raw suppliers

Pentadecanolide ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCCCCCCOC(=O)CCCCCC1
• Uses: As a fixative in perfumery. Pentadecanolide is a monomer used to make PGA-co-pentadecalactone polymers to be used in the development of directly compressed prolonged release tablets of slightly soluble drugs such as ketoprofen. Pentadecanolide may be used for the synthesis of poly(pentadecanolide) (PPDL) by Novozyme 435 catalyzed ring-opening polymerization. It may be employed as starting reagent for the synthesis of terminally-branched iso-fatty acids (iso-C15-C17).

Technology Process of Oxacyclohexadecan-2-one

There total 149 articles about Oxacyclohexadecan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(E/Z)-oxacyclohexadec-11-en-2-one (76293-72-6,76293-73-7,4941-77-9) → pentadecanolide (106-02-5,81031-90-5)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethyl acetate; at 20 ℃; for 16h; under 760.051 Torr; Solvent; Concentration; Schlenk technique; Glovebox;

DOI:10.1039/c8cy02115e

Reference yield: 99.0%

E-Pentadec-2-ene-15-olide (87227-39-2) → pentadecanolide (106-02-5,81031-90-5)

Guidance literature:

With hydrogen; palladium on activated charcoal;

Reference yield: 99.0%

(E)-6-pentadecen-15-olide (63294-84-8) → pentadecanolide (106-02-5,81031-90-5)

Guidance literature:

With hydrogen; palladium-barium carbonate; for 3h; under 1520 Torr; Ambient temperature;

DOI:10.1021/ja00534a030

upstream raw materials:

15-hydroxylpentadecanoic acid

cyclopentadecanone

15-bromo-pentadecanoic acid

12-oxo-15-pentadecanolide

Downstream raw materials:

15-hydroxy-pentadecanoic acid hydrazide

methyl 15-hydroxypentadecanoate

15-bromopentadecane-1-ol

triacontane-1,30-diol

Refernces

• 1、 Cossy, J.,Pete, J.P.. "A THREE STEP SYNTHESIS OF EXALTOLIDE AND PHORACANTHOLIDE I". . p. 2369 - 2370. Retrieved 1986.
• 2、 Galli, Carlo,Mandolini, Luigi. "Lack of a "Cesium Effect" on Macrolactonization". . p. 3045 - 3047. Retrieved 1991.
• 3、 White,Green,Fleming. "Tin(IV)-catalyzed lactonization of ω-hydroxy trifluoroethyl esters". . p. 3515 - 3518. Retrieved 1993.
• 4、 Sato, Toshio,Kawara, Tatsuo,Kokubu, Yasuchika,Fujisawa, Tamotsu. "A Simple Method for the Synthesis of Exaltolide". . p. 945 - 946. Retrieved 1981.
• 5、 Trost, Barry M,Chisholm, John D. "An acid-catalyzed macrolactonization protocol.". . p. 3743 - 3745. Retrieved 2002.
• 6、 Nishio, Yuya,Kawazu, Akari,Hirano, Shun,Matsubara, Hiroshi. "Preparation of fluorous Yamaguchi reagents and evaluation of their reactivity in esterification". . p. 720 - 725. Retrieved 2016.
• 7、 Sanz-Navarro, Sergio,Garnes-Portolés, Francisco,López-Cruz, Carlos,Espinós-Ferri, Estela,Corma, Avelino,Leyva-Pérez, Antonio. "Radical α–alkylation of ketones with unactivated alkenes under catalytic and sustainable industrial conditions". . . Retrieved 2021.
• 8、 Ookoshi, Tooru,Onaka, Makoto. "Zeolite-catalyzed macrolactonization of ω-hydroxyalkanoic acids in a highly concentrated solution". . p. 293 - 296. Retrieved 1998.
• 9、 Ruddick, Clare L.,Hodge, Philip,Cook, Anthony,McRiner, Andrew J.. "A new method for the polymer-supported synthesis of cyclic oligoesters for potential applications in macrocyclic lactone synthesis and combinatorial chemistry". . p. 629 - 637. Retrieved 2002.
• 10、 Kamae, Kenichiro,Obora, Yasushi,Ishii, Yasutaka. "Baeyer-villiger oxidation of cycloalkanones with in situ generated hydrogen peroxide from alcohols and molecular oxygen using NHPI as a key catalyst". . p. 891 - 895. Retrieved 2009.