5989-02-6

Basic information

• Product Name: loliolide
• Synonyms: loliolide;5,6,7,7a-Tetrahydro-4,4,7aα-trimethyl-6α-hydroxybenzofuran-2(4H)-one;5,6,7,7a-Tetrahydro-6α-hydroxy-4,4,7aα-trimethylbenzofuran-2(4H)-one;Digiprolactone;Caulilide;Loliolid;NSC 289632;2(4H)-Benzofuranone,5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-, (6S,7aR)-
• CAS NO: 5989-02-6
• Molecular Formula: C11H16O3
• Molecular Weight: 196.24294
• Mol File: 5989-02-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 151-153℃
• Boiling Point: 352.7°C at 760 mmHg
• Flash Point: 153.7°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 2.19E-06mmHg at 25°C
• Refractive Index: 1.529
• PKA: 14.39±0.60(Predicted)
• CAS DataBase Reference: loliolide(CAS DataBase Reference)
• NIST Chemistry Reference: loliolide(5989-02-6)
• EPA Substance Registry System: loliolide(5989-02-6)

Safety Data

• Hazardous Substances Data: 5989-02-6(Hazardous Substances Data)

Usage

Definition

ChEBI: A natural product found in Brachystemma calycinum.

InChI:InChI=1/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11+/m0/s1

Upstream product

• 147730-47-0 (S)-actinidiolide 
• 1133-01-3 hexahydro-3aα,4,5,6,7,7aα (3H) hydroxy-6 trimethyl-4,4,7α benzofurannone-2 
• 87164-34-9 (3R,3aS,6R,7aS)-4,4,7a-Trimethyl-3-phenylselanyl-6-(tetrahydro-pyran-2-yloxy)-hexahydro-benzofuran-2-one 
• 79499-04-0 (3aS,5S,7aS)-4,4,7a-Trimethyl-5-phenylselanyl-hexahydro-benzofuran-2-one 
• 87164-37-2 (3aR,5S,7aR)-5-Iodo-4,4,7a-trimethyl-hexahydro-benzofuran-2-one 
• 66901-56-2 (3aR,5S,7aR)-5-Bromo-4,4,7a-trimethyl-hexahydro-benzofuran-2-one 
• 87164-41-8 (3aR,6S,7aR)-4,4,7a-Trimethyl-6-(tetrahydro-pyran-2-yloxy)-hexahydro-benzofuran-2-one 
• 87164-36-1 C₁₁H₁₇HgIO₂ 
• 71041-56-0 C₁₁H₁₇BrHgO₂ 
• 87164-39-4 (3aR,5R,6R,7aR)-5-Bromo-6-hydroxy-4,4,7a-trimethyl-hexahydro-benzofuran-2-one 
• 1133-01-3 (3aR,6S,7aR)-6-Hydroxy-4,4,7a-trimethyl-hexahydro-benzofuran-2-one 
• 79693-70-2 (3aR,7aR)-4,4,7a-Trimethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one 
• 87164-37-2 hexahydro-3aα,4,5,6,7,7aα (3H) iodo-5β trimethyl-4,4,7a benzofurannone-2 
• 79693-70-2 tetrahydro-3aα,4,7,7aα (3H) trimethyl-4,4,7a benzofurannone-2 

Relevant articles and documents

Synthesis of loliolide, actinidiolide, dihydroactinidiolide, and aeginetolide via cerium enolate chemistry

(Chemical Equation Presented) Loliolide, aeginetolide, actinidiolide, and dihydroactinidiolide were synthesized in racemic form from a single common intermediate, prepared through the 1,2 addition of the cerium enolate of ethyl acetate to 2,6,6-trimethylcylohexenone.

Carotenoids and Degraded Carotenoids, VIII. Synthesis of (+)-Dihydroactinidiolide, (+)- and (-)-Actinidiolide, (+)- and (-)-Loliolide as well as (+)- and (-)-Epiloliolide

Enantiomerically pure (S)-2,4,4-trimethyl-2-cyclohexen-1-ol (1) was efficiently converted into four degraded lactonic carotenoids: (S)-dihydroactinidiolide (5), (S)-actinidiolide (9), (6S,7aR)-loliolide (11) and (6S,7aS)-epiloliolide (12). (R)-Actinidioli

SYNTHESE DU (+/-) LOLIOLIDE PAR POLYCYCLISATION DE L'ACIDE HOMOGERANIQUE.

A new synthesis of (+/-) loliolide was achieved from pure homogeranic acid in a stereospecific fashion.The intermediate ethylenic lactone 6 was converted to the racemate of lol