Desacetoxymatricarin

Base Information

• Chemical Name: Desacetoxymatricarin
• CAS No.: 17946-87-1
• Deprecated CAS: 68247-35-8
• Molecular Formula: C15H18O3
• Molecular Weight: 246.3016
• UNII: 1G2W00IRUI
• DSSTox Substance ID: DTXSID20170810
• Nikkaji Number: J15.382F
• Wikidata: Q27106383
• Metabolomics Workbench ID: 141499
• ChEMBL ID: CHEMBL517040
• Mol file: 17946-87-1.mol

Synonyms:desacetoxymatricarin;leucodin

Chemical Property of Desacetoxymatricarin

Chemical Property:

• Vapor Pressure: 8.24E-08mmHg at 25°C
• Melting Point: 208℃
• Boiling Point: 436.2°Cat760mmHg
• Flash Point: 195.8°C
• PSA: 43.37000
• Density: 1.18g/cm³
• LogP: 2.41960
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 246.125594432
• Heavy Atom Count: 18
• Complexity: 498

Purity/Quality:

98%Min ^*data from raw suppliers

Leucomisine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CCC(=C3C(C2OC1=O)C(=CC3=O)C)C
• Isomeric SMILES: C[C@H]1[C@@H]2CCC(=C3[C@@H]([C@H]2OC1=O)C(=CC3=O)C)C
• Uses: Leucomisine is an antiinflammatory and angioprotective sesquiterpene.

Technology Process of Desacetoxymatricarin

There total 7 articles about Desacetoxymatricarin 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: 86.0%

(1S,2S,6S)-9,13-dimethyl-5-methylene-3-oxatricyclo[8.3.0.0(2,6)]trideca-9,12-diene-4,11-dione (36150-07-9) → 11,13-dihydrodehydroleucodin (17946-87-1)

Guidance literature:

With sodium tetrahydroborate; cobalt(II) chloride; In methanol; dichloromethane; at -20 ℃; for 6h;

DOI:10.1021/jm00091a013

Reference yield:

C16H20O7S (113394-01-7) → achillin (5181-80-6,5956-04-7,17946-87-1,81024-40-0)

Guidance literature:

With zinc; In 1,2-dimethoxyethane; for 1.5h; Yield given; Heating;

Reference yield:

1,10-epoxy-8α-hydroxyachillin (61866-57-7,80876-77-3,113472-28-9,137695-13-7) → achillin (5181-80-6,5956-04-7,17946-87-1,81024-40-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 24 h / Ambient temperature; 1.) 0 deg C

2: activated zinc / 1,2-dimethoxy-ethane / 1.5 h / Heating

With zinc; In pyridine; 1,2-dimethoxyethane;

upstream raw materials:

C₁₆H₂₀O₇S

1,10-epoxy-8α-hydroxyachillin

(1S,2S,6S)-9,13-dimethyl-5-methylene-3-oxatricyclo[8.3.0.0(2,6)]trideca-9,12-diene-4,11-dione

Downstream raw materials:

1α,10α-epoxydesacetoxymatricarin

Refernces

• 1、 Galvis, Adriana,Marcano, Adriana,Stefancin, Chad,Villaverde, Nicole,Priestap, Horacio A.,Tonn, Carlos E.,Lopez, Luis A.,Barbieri, Manuel A.. "The effect of dehydroleucodine in adipocyte differentiation". body text. p. 18 - 25. Retrieved 2012/06/04.
• 2、 Collado, Isidro G.,Macias, Francisco A.,Massanet, Guillermo M.,Luis, Francisco R.. "Configuration of 1,10-Epoxyguaianolides: Stereochemistry of 1,10-Epoxy-8α-hydroxyachillin". . p. 1641 - 1644. Retrieved 2007/10/02.