Artemisiifolin

Base Information

• Chemical Name: Artemisiifolin
• CAS No.: 26931-87-3
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• DSSTox Substance ID: DTXSID901104448
• NSC Number: 177852
• Wikidata: Q27105848
• Mol file: 26931-87-3.mol

Synonyms:Artemisiifolin;26931-87-3;Artemisulfolin;(3aS,4R,5Z,9E,11aS)-4-hydroxy-6-(hydroxymethyl)-10-methyl-3-methylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2-one;ARTEMISIIFOLINE;C09304;CHEBI:2851;DTXSID901104448;NSC177852;Q27105848;(3aS,4R,5Z,9E,11aS)-3a,4,7,8,11,11a-Hexahydro-4-hydroxy-6-(hydroxymethyl)-10-methyl-3-methylenecyclodeca[b]furan-2(3H)-one;Cyclodeca[b]furan-2(3H)-one,4,7,8,11,11a-hexahydro-4-hydroxy-6-(hydroxymethyl)-10-methyl-3-methylene-, [3aS-(3aR*,4S*,5Z,9E,11aR*)]-

Chemical Property of Artemisiifolin

Chemical Property:

• Vapor Pressure: 2.72E-12mmHg at 25°C
• Melting Point: 130 - 132 °C
• Boiling Point: 504.5°Cat760mmHg
• Flash Point: 190.3°C
• PSA: 66.76000
• Density: 1.2g/cm³
• LogP: 1.49400
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 264.13615911
• Heavy Atom Count: 19
• Complexity: 447

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(=CC(C2C(C1)OC(=O)C2=C)O)CO
• Isomeric SMILES: C/C/1=C\CC/C(=C/[C@H]([C@H]2[C@H](C1)OC(=O)C2=C)O)/CO

Technology Process of Artemisiifolin

There total 5 articles about Artemisiifolin 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: 77.0%

(6R,7S,8S,1R)-8-[(1,2-dihydroxyethyl)acroyloyl]-15-hydroxygermacra-1(10),4,11(13)-trien-6,12-olide → (6R,7S,8S)-6,15-dihydroxygermacra-1(10),4,11(13)-trien-8,12-olide (26931-87-3)

Guidance literature:

With water; potassium hydroxide; at 20 ℃; for 4h;

DOI:10.1002/ejoc.201000171

Reference yield:

(6R,7R,8S,1″R)-8-[(1″,2″-dihydroxyethyl)acryloyl]-15-hydroxygermacra-1(10),4,11(13)-trien-6,12-olide → (6R,7S,8S)-6,15-dihydroxygermacra-1(10),4,11(13)-trien-8,12-olide (2571-82-6,26931-87-3)

Guidance literature:

With water; sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 1h;

DOI:10.1021/acs.joc.8b00407

Reference yield:

salonitenolide (26931-94-2) → (6R,7S,8S)-6,15-dihydroxygermacra-1(10),4,11(13)-trien-8,12-olide (26931-87-3)

Guidance literature:

With potassium carbonate;

DOI:10.1021/ol034510k

upstream raw materials:

salonitenolide

Downstream raw materials:

isabelin

(+)-β-cyclopyrethrosin

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