Oxacycloheptadecan-2-one

Base Information

• Chemical Name: Oxacycloheptadecan-2-one
• CAS No.: 109-29-5
• Molecular Formula: C16H30 O2
• Molecular Weight: 254.413
• Hs Code.: 2932209090
• European Community (EC) Number: 203-662-0
• NSC Number: 33546
• UNII: 64E2HO00C7
• DSSTox Substance ID: DTXSID4047622
• Nikkaji Number: J65.679H
• Wikidata: Q21099108
• Metabolomics Workbench ID: 4388
• ChEMBL ID: CHEMBL3189021
• Mol file: 109-29-5.mol

Synonyms:hexadecanolide

Chemical Property of Oxacycloheptadecan-2-one

Chemical Property:

• Appearance/Colour: colourless to light yellow solid
• Vapor Pressure: 2.6E-05mmHg at 25°C
• Melting Point: 34-38 °C(lit.)
• Refractive Index: n20/D1.4680-1.4730
• Boiling Point: 188 °C / 15mmHg
• Flash Point: 149.6°C
• PSA: 26.30000
• Density: 0.879g/cm³
• LogP: 5.00460
• Storage Temp.: −20°C
• Water Solubility.: Insoluble in water.
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 254.224580195
• Heavy Atom Count: 18
• Complexity: 201

Purity/Quality:

99.9% ^*data from raw suppliers

16-Hexadecanolide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCCCCCCC(=O)OCCCCCCC1
• General Description: 16-Hexadecanolide, also known as dihydroambrettolide, is a macrocyclic lactone derived from the lactonization of 16-hydroxyhexadecanoic acid. It can be synthesized through catalytic hydrogenation of Δ⁹-isoambrettolide or via lactonization reactions using catalysts like hydrous zirconium(IV) oxide or amphiphilic carboxyl-activating agents. 16-HEXADECANOLIDE is structurally related to other macrocyclic lactones and is used in fragrance and flavor applications due to its musky odor. The yield of 16-hexadecanolide can be influenced by reaction conditions, including micellar effects in cyclization processes.

Technology Process of Oxacycloheptadecan-2-one

There total 39 articles about Oxacycloheptadecan-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: 98.0%

(10E/Z)-oxacycloheptadec-10-en-2-one (28645-51-4) → 15-hexadecanolide (109-29-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In diethyl ether; under 760 Torr;

DOI:10.1055/s-1987-27867

Reference yield: 97.0%

16-hydroxyhexadecanoic acid (506-13-8) → 15-hexadecanolide (109-29-5)

Guidance literature:

With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; chloroform; for 18h; Reflux; Inert atmosphere;

DOI:10.1039/c0ob00161a

Reference yield: 93.0%

(Z)-Oxacycloheptadec-15-en-2-one → 15-hexadecanolide (109-29-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; Ambient temperature;

DOI:10.1039/c39810001123

upstream raw materials:

16-bromohexadecanoic acid

16-hydroxyhexadecanoic acid

cyclohexadecanone

16-iodohexadecanoic acid

Downstream raw materials:

ω-phenyl pentadecanoic acid methyl ester

1,16-dibromohexadecane

16-bromohexadecan-1-ol