Loliolide

Base Information

• Chemical Name: Loliolide
• CAS No.: 5989-02-6
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.246
• UNII: U3BB4IM281
• DSSTox Substance ID: DTXSID501019112
• Nikkaji Number: J16.007E
• Wikidata: Q27138116
• Metabolomics Workbench ID: 127715
• ChEMBL ID: CHEMBL227113
• Mol file: 5989-02-6.mol

Synonyms:1,3-dihydroxy-3,5,5-trimethylcyclohexylidene-4-acetic acid lactone;loliolide

Chemical Property of Loliolide

Chemical Property:

• Vapor Pressure: 2.19E-06mmHg at 25°C
• Melting Point: 151-153℃
• Boiling Point: 352.7°C at 760 mmHg
• PKA: 14.39±0.60(Predicted)
• Flash Point: 153.7°C
• PSA: 46.53000
• Density: 1.16g/cm³
• LogP: 1.40920
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 196.109944368
• Heavy Atom Count: 14
• Complexity: 317

Purity/Quality:

98%,99%, ^*data from raw suppliers

Loliolide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC(CC2(C1=CC(=O)O2)C)O)C
• Isomeric SMILES: C[C@@]12C[C@H](CC(C1=CC(=O)O2)(C)C)O

Technology Process of Loliolide

There total 54 articles about Loliolide 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: 94.0%

(6S,7R,7aS)-7-bromo-6-hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one (147804-31-7) → Loliolide (1133-03-5,5989-02-6,10309-35-0,10481-90-0,33824-59-8,38274-00-9,61927-07-9,81444-64-6,147730-52-7)

Guidance literature:

With tri-n-butyl-tin hydride; In tetrahydrofuran; for 4h; Ambient temperature;

Reference yield: 86.0%

(+/-)-7-bromo-6-hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydro-1-benzofuran-2(4H)-one → (+/-)-loliolide (1133-03-5,5989-02-6,10309-35-0,10481-90-0,33824-59-8,38274-00-9,61927-07-9,81444-64-6,147730-52-7)

Guidance literature:

With tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile); In hexane; for 4h; Heating;

DOI:10.1021/jo0611566

Reference yield: 85.0%

(6R,7S,7aR)-7-bromo-6-hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one (147641-88-1) → loliolide (1133-03-5,5989-02-6,10309-35-0,10481-90-0,33824-59-8,38274-00-9,61927-07-9,147730-52-7,81444-64-6)

Guidance literature:

With tri-n-butyl-tin hydride; In tetrahydrofuran; for 4h; Ambient temperature;

upstream raw materials:

(6S,7R,7aS)-7-bromo-6-hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one

6-(tert-butyl-dimethyl-silanyloxy)-4,4,7a-trimethyl-5,6,7,7a-tetrahydro-4H-benzofuran-2-one

(-)-[(S)-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-enyl]methanol

(-)-(1S,4S,6R)-4-(tert-butyldimethylsilyloxy)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane-1-carbaldehyde

Refernces

• 1、 Kuba, Masako,Furuichi, Noriyuki,Katsumura, Shigeo. "Stereocontrolled syntheses of carotenoid oxidative metabolites, (-)-loliolide, (-)-xanthoxin, and their stereoisomers". . p. 1248 - 1249. Retrieved 2007/10/03.
• 2、 Zamarlik, Henri,Gnonlonfoun, Noukpo,Rouessac, Francis. "Syntheese du (+/-)-loliolide ou hydroxy-6 teetrahydro-5,6,7,7a trimeethyl-4,4,7a(4H) benzofurannone-2 (6S,7aR) par cyclisation de l'acide homogeeranique". . p. 2326 - 2329. Retrieved 2007/10/02.