Massoia lactone

Base Information

• Chemical Name: Massoia lactone
• CAS No.: 54814-64-1
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.236
• European Community (EC) Number: 259-359-9
• NSC Number: 720841
• UNII: KUC3Q7KGG6
• DSSTox Substance ID: DTXSID80866186
• Nikkaji Number: J39.627C
• Wikipedia: Massoia_lactone
• Wikidata: Q106653706
• Metabolomics Workbench ID: 46555
• ChEMBL ID: CHEMBL1991946
• Mol file: 54814-64-1.mol

Synonyms:Massoia lactone;54814-64-1;Massoilactone;5-hydroxy-2-decenoic acid lactone;2-pentyl-2,3-dihydropyran-6-one;2H-Pyran-2-one, 5,6-dihydro-6-pentyl-;Cocolactone;(+/-)-Massoilactone;5,6-Dihydro-6-pentyl-2H-pyran-2-one;6-Pentyl-5,6-dihydro-2H-pyran-2-one;2-decen-5-olide;KUC3Q7KGG6;Massoilactone, (+/-)-;5-Hydroxy-2-decenoic acid delta-lactone;5-Hydroxy-2-decenoic acid, delta-lactone;FEMA No. 3744;6-pentyl-5,6-dihydropyran-2-one;5-Hydroxy-2-decenoic acid, lactone;EINECS 259-359-9;5-Hydroxy-2-decenoic acid, delta-lactone (natural);BRN 4177048;(R)-(-)-Massoilactone;C-10 massoia lactone;5,6-Dihydro-6-pentyl-2H-pyran-2-one, (R)-;5-HYDROXY-2-DECENOICACIDLACTONE;Massoialactone;Massoy lactone;(+/-)-MASSOIA LACTONE;5-Hydroxy-2-decenoic acid .delta.-lactone;(R)-massoia lactone;C-10-Massoia lactone;2-Deceno-delta-lactone;UNII-KUC3Q7KGG6;2H-Pyran-2-one, 5,6-dihydro-6-pentyl-, (theta)-;(.+/-.)-Massoilactone;SCHEMBL1686964;CHEMBL1991946;FEMA 3744;DTXSID80866186;DEC-2-ENO-1,5-LACTONE;(+/-)-MASSOJA DECALACTONE;HY-N7435;6-pentyl-5,6-dihydro-pyran-2-one;NSC720841;5-Hydroxy-2-decenoic acid D-lactone;NSC-720841;Massoia Lactone, natural, >=95%, FG;(6R)-6-pentyl-5,6-dihydropyran-2-one;NCI60_041415;6-Pentyl-5,6-dihydro-2H-pyran-2-one #;LS-127437;CS-0128864;FT-0605071;FT-0620464;(R)-5,6-Dihydro-6-pentyl-2H-pyran-2-one;5,6-Dihydro-6-pentyl-(R)-2H-Pyran-2-one;5,6-Dihydro-6-pentyl-(6R)-2H-Pyran-2-one;5,6-Dihydro-6-pentyl-(theta)-2H-Pyran-2-one;5-Hydroxy-2-decenoic acid laquo deltaRaquo -lactone;Q6784821;2-DECENOIC ACID, 5-HYDROXY-, .DELTA.-LACTONE;5,6 - dihydro - 6 - pentyl - 2H - pyran - 2 - one;501-23-5

Chemical Property of Massoia lactone

Chemical Property:

• Boiling Point: 287 °C at 760 mmHg
• Flash Point: 115.8 °C
• PSA: 26.30000
• Density: 0.964 g/cm³
• LogP: 2.43840
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

99%, ^*data from raw suppliers

(±)-Massoilactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC1CC=CC(=O)O1
• Uses: (±)-Massoilactone is a main chemical component found in many types of volatile oils and has antibacterial activity in vitro.

Technology Process of Massoia lactone

There total 225 articles about Massoia lactone 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: 86.0%

(R)-non-1-en-4-yl acrylate (263238-28-4) → (R)-massoialactone (51154-96-2,54814-64-1)

Guidance literature:

With Grubbs catalyst first generation; titanium(IV) isopropylate; In dichloromethane; Reflux; Inert atmosphere;

DOI:10.1055/s-0030-1260051

Reference yield: 82.0%

(2Z,5R)-dec-2-ene-1,5-diol (1298100-56-7) → (R)-massoialactone (51154-96-2,54814-64-1)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1055/s-0032-1318440

Reference yield: 78.0%

C28H35NO4 → (6S)-6-pentyl-5,6-dihydro-2H-pyran-2-one (61248-45-1,54814-64-1)

Guidance literature:

With trimethylphosphane; In dichloromethane; toluene; at 20 ℃; for 0.25h;

DOI:10.1055/s-0036-1589162

upstream raw materials:

(+/-)-5-hydroxy-dec-2c-enoic acid methyl ester

(Z)-1-bromo-1-nonen-4-ol

trans-2-methoxy-6-pentyl-5,6-dihydro-2H-pyran

tert-butyl (Z)-5-hydroxy-2-decenoate

Downstream raw materials:

(R)-massoialactone

(6S)-6-pentyl-5,6-dihydro-2H-pyran-2-one

Refernces

• 1、 Bodnar, Alexandra K.,Butcher, Will,Huang, David,Lew, Joanna K.,Newhouse, Timothy R.,Turlik, Aneta. "Preparation of hindered aniline cyanh and application in the allyl-ni-catalyzed α,β-dehydrogenation of carbonyls". . p. 263 - 288. Retrieved 2021/10/19.
• 2、 Huang, David,Szewczyk, Suzanne M.,Zhang, Pengpeng,Newhouse, Timothy R.. "Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones". supporting information. p. 5669 - 5674. Retrieved 2019/04/26.