(R)-5-Hexadecanolide

Base Information

• Chemical Name: (R)-5-Hexadecanolide
• CAS No.: 59812-96-3
• Molecular Formula: C16H30O2
• Molecular Weight: 254.4082
• UNII: DLX2RFQ9UW
• Nikkaji Number: J731E
• Mol file: 59812-96-3.mol

Synonyms:(R)-5-HEXADECANOLIDE;59812-96-3;DLX2RFQ9UW;(6R)-6-undecyloxan-2-one;Fema No. 4673, (R)-;UNII-DLX2RFQ9UW;delta-Palmitolactone, (R)-;2H-Pyran-2-one, tetrahydro-6-undecyl-, (6R)-;(R)-5-HEXADECANOLIDE STANDARD FOR GC;.DELTA.-PALMITOLACTONE, (R)-;(6R)-tetrahydro-6-undecyl-2H-pyran-2-one

Chemical Property of (R)-5-Hexadecanolide

Chemical Property:

• PSA: 26.30000
• LogP: 5.00300
• Storage Temp.: ?20°C
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 254.224580195
• Heavy Atom Count: 18
• Complexity: 213

Purity/Quality:

97% ^*data from raw suppliers

(R)-5-HEXADECANOLIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC1CCCC(=O)O1
• Isomeric SMILES: CCCCCCCCCCC[C@@H]1CCCC(=O)O1

Technology Process of (R)-5-Hexadecanolide

There total 93 articles about (R)-5-Hexadecanolide 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: 97.0%

(R)-((E)-6-Undec-4-enyl)-tetrahydro-pyran-2-one (110720-08-6) → (R)-5-hexadecanolide (59812-96-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In diethyl ether; for 2h; under 760 Torr; Ambient temperature;

DOI:10.1021/jo00003a038

Reference yield: 91.0%

(R)-(-) 5-hydroxy hexadecanenitrile (90472-99-4) → (R)-5-hexadecanolide (59812-96-3)

Guidance literature:

With NaCO₃; In ethanol; water; for 12h; Heating;

DOI:10.1016/S0040-4020(01)91246-3

Reference yield: 90.0%

(R)-5-Benzyloxy-hexadecanoic acid (86838-53-1) → (R)-5-hexadecanolide (59812-96-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/S0040-4039(00)81833-X

upstream raw materials:

hydroxyhexadecanoic acid

5-oxohexadecanoic acid

Methyl 5-hydroxyhexadecanoate

(R)-5-hydroxyhexadecanoic acid

Refernces

• 1、 Coutrot Ph.,Grison,Bomont. "5-Formyl-δ-valerolactone: A useful synthon for the chiral synthesis of the vespa Orientalis pheromone and the mosquito oviposition attractant pheromone". . p. 8381 - 8384. Retrieved 1994.
• 2、 Harbindu, Anand,Sharma, Brijesh M.,Kumar, Pradeep. "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". . p. 305 - 314. Retrieved 2013/04/24.
• 3、 Marion,Le Fol,Courillon,Malacria. "One-pot diastereoselective preparation of α,β-unsaturated-γ-silylated-δ-lactones: Application towards natural compounds". . p. 138 - 140. Retrieved 2007/10/03.