Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, [3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta)]-

Base Information

• Chemical Name: Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, [3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta)]-
• CAS No.: 22489-66-3
• Molecular Formula: C15H18 O4
• Molecular Weight: 262.306
• NSC Number: 295425
• Wikidata: Q105348154
• Metabolomics Workbench ID: 125866
• ChEMBL ID: CHEMBL1968792
• Mol file: 22489-66-3.mol

Synonyms:NSC295425;Grosheimine;SCHEMBL1711493;CHEMBL1968792;YGMIBVIKXJJQQJ-UHFFFAOYSA-N;NCI60_002463;4-Hydroxy-9-methyl-3,6-dimethyleneoctahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione #;4-.beta.-H-Guaia-10(14),11(13)-dien-12-oic acid, 6-.alpha.,8-.alpha.-dihydroxy-3-oxo-,12,6-lactone;4-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno [4,5-b]furan-2,8-dione;Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, [3aR-(3a.alpha.,4.alpha.,6a.alpha.,9.alpha.,9a.alpha.,9b.beta.)]-

Chemical Property of Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, [3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta)]-

Chemical Property:

• Vapor Pressure: 2.93E-11mmHg at 25°C
• Boiling Point: 480.7°C at 760 mmHg
• Flash Point: 183.2°C
• Density: 1.24g/cm³
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 262.12050905
• Heavy Atom Count: 19
• Complexity: 492

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(CC1=O)C(=C)CC(C3C2OC(=O)C3=C)O

Technology Process of Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, [3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta)]-

There total 19 articles about Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, [3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta)]- 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:

crepiside D (100187-62-0,100228-51-1) → grosheimin (22489-66-3)

Guidance literature:

With hesperidinase; In water; at 37 ℃; for 3h;

Reference yield:

grosheiminol (84305-03-3) → grosheimin (22489-66-3)

Guidance literature:

With chromium(VI) oxide; In water; acetic acid; at 0 ℃; for 48h;

Reference yield:

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-(2,3,5,6-tetrafluoro-phenylsulfanylmethyl)-octahydro-azuleno[4,5-b]furan-2,8-dione → grosheimin (22489-66-3) + 2,3,5,6-tetrafluorothiophenol (769-40-4)

Guidance literature:

With phosphate buffer; In methanol; at 37 ℃; pH=7.4; Kinetics;

DOI:10.1016/S0223-5234(99)80100-7

upstream raw materials:

grosheiminol

crepiside D

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-phenylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-m-tolylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione

Downstream raw materials:

11-H-13-Se-phenyl grosheimin

11-H, 13-ethoxy grosheimin

cynarascolide

grosheiminol

Refernces

• 1、 Miyase, Toshio,Ueno, Akira,Noro, Tadataka,Kuroyanagi, Masanori,Fukushima, Seigo. "Studies on Sesquiterpene Glycosides from Crepis japonica BENTH.". . p. 4451 - 4456. Retrieved 2007/10/02.