(Z)-4-Hydroxy-6-dodecenoic acid lactone

Base Information

• Chemical Name: (Z)-4-Hydroxy-6-dodecenoic acid lactone
• CAS No.: 18679-18-0
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• European Community (EC) Number: 242-497-9
• UNII: O8B631XC2S
• DSSTox Substance ID: DTXSID601016535
• Nikkaji Number: J127.244F
• Wikipedia: (Z)-6-Dodecen-4-olide
• Wikidata: Q27285474
• Metabolomics Workbench ID: 72155
• Mol file: 18679-18-0.mol

Synonyms:cis-4-hydroxydodec-6-enoic acid lactone

Chemical Property of (Z)-4-Hydroxy-6-dodecenoic acid lactone

Chemical Property:

• Vapor Pressure: 0.000573mmHg at 25°C
• Boiling Point: 311.2°Cat760mmHg
• Flash Point: 127.5°C
• PSA: 26.30000
• Density: 0.95g/cm³
• LogP: 3.21860
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 196.146329876
• Heavy Atom Count: 14
• Complexity: 197

Purity/Quality:

99%, ^*data from raw suppliers

(Z)-4-HYDROXY-6-DODECENOIC ACID LACTONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC1CCC(=O)O1
• Isomeric SMILES: CCCCC/C=C\CC1CCC(=O)O1

Technology Process of (Z)-4-Hydroxy-6-dodecenoic acid lactone

There total 5 articles about (Z)-4-Hydroxy-6-dodecenoic acid 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: 88.0%

ethyl 3-(oxiran-2-yl)propanoate (73697-60-6) → 2(3H)-furanone, dihydro-5-(2-octenyl)-, (Z)- (15456-69-6,60551-23-7,63357-98-2,63357-99-3,127127-84-8,18679-18-0)

Guidance literature:

In diethyl ether; 1.) -30 deg C --> -10 deg C, 1 h 2.) -10 deg C, 1h;

DOI:10.1016/0040-4020(80)80209-2

Reference yield:

ethyl 4-pentenoate (1968-40-7) → 2(3H)-furanone, dihydro-5-(2-octenyl)-, (Z)- (15456-69-6,60551-23-7,63357-98-2,63357-99-3,127127-84-8,18679-18-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / MCPBA / CH₂Cl₂

2: 88 percent / diethyl ether / 1.) -30 deg C --> -10 deg C, 1 h 2.) -10 deg C, 1h

With 3-chloro-benzenecarboperoxoic acid; In diethyl ether; dichloromethane;

DOI:10.1016/0040-4020(80)80209-2

Reference yield:

hexyltriphenylphosphonium bromide (4762-26-9) + γ-(prop-2-enyl)-γ-butyrolactone (134359-16-3) → 2(3H)-furanone, dihydro-5-(2-octenyl)-, (Z)- (15456-69-6,60551-23-7,63357-98-2,63357-99-3,127127-84-8,18679-18-0)

Guidance literature:

With n-butyllithium; hydrogen; ozone; palladium on activated charcoal; Yield given. Multistep reaction; 1.) EtOAc, -70 deg C; 2.) EtOAc, -10 deg C, then Rt; 3.) hexane, toluene, -70 deg C to Rt, 1 h;

DOI:10.1002/hlca.19820650204

upstream raw materials:

hexyltriphenylphosphonium bromide

γ-(prop-2-enyl)-γ-butyrolactone

<9,10-2H2>-oleic acid

ethyl 3-(oxiran-2-yl)propanoate

Refernces

• 1、 Maurer, Bruno,Hauser, Arnold. "Identification and Synthesis of New γ-Lactones from Tuberose Absolute (Polianthes tuberosa)". . p. 462 - 476. Retrieved 2007/10/02.