Arucadiol

Base Information

• Chemical Name: Arucadiol
• CAS No.: 105037-85-2
• Molecular Formula: C19H22 O3
• Molecular Weight: 298.382
• DSSTox Substance ID: DTXSID901318625
• Nikkaji Number: J323.578E
• Wikidata: Q104396498
• Metabolomics Workbench ID: 124973
• ChEMBL ID: CHEMBL1813350
• Mol file: 105037-85-2.mol

Synonyms:Arucadiol;105037-85-2;5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3-dihydrophenanthren-4-one;5,6-Dihydroxy-7-isopropyl-1,1-dimethyl-2,3-dihydrophenanthren-4(1H)-one;MILTIODIOL;CHEMBL1813350;DTXSID901318625;AKOS040736402;FS-7557;5,6-dihydroxy-7-isopropyl-1,1-dimethyl-2,3-dihydrophenanthren-4-one

Chemical Property of Arucadiol

Chemical Property:

• PSA: 57.53000
• LogP: 4.62850
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 298.15689456
• Heavy Atom Count: 22
• Complexity: 442

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C(=C2C(=C1)C=CC3=C2C(=O)CCC3(C)C)O)O

Technology Process of Arucadiol

There total 4 articles about Arucadiol 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: 95.0%

7‐isopropyl‐5,6‐dimethoxy‐1,1‐dimethyl‐2,3‐dihydrophenanthren‐4 (1H)‐one (195001-37-7) → 5,6‐dihydroxy‐7‐isopropyl‐1,1‐dimethyl‐2,3‐dihydrophenanthren‐4(1H)‐one (105037-85-2)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 0 ℃; for 2h;

DOI:10.1021/jo970570q

Reference yield:

miltirone (27210-57-7) → 5,6‐dihydroxy‐7‐isopropyl‐1,1‐dimethyl‐2,3‐dihydrophenanthren‐4(1H)‐one (105037-85-2)

Guidance literature:

With Methyl oleate; rose bengal; at 60 ℃; for 1560h; Mechanism; Irradiation; identification of potential mechanism in light-induced oxidation and autoxidation systems containing either stripped bulk soybean oils (SBO) or purified methyl oleate;

DOI:10.1007/s11746-998-0127-3

Reference yield:

7-Isopropyl-5,6-dimethoxy-1,1-dimethyl-2,3,9,10-tetrahydro-1H-phenanthren-4-one (153661-62-2) → 5,6‐dihydroxy‐7‐isopropyl‐1,1‐dimethyl‐2,3‐dihydrophenanthren‐4(1H)‐one (105037-85-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / DDQ / benzene / 12 h / Heating

2: 95 percent / BBr₃ / CH₂Cl₂ / 2 h / -78 - 0 °C

With boron tribromide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; benzene;

DOI:10.1021/jo970570q

upstream raw materials:

7‐isopropyl‐5,6‐dimethoxy‐1,1‐dimethyl‐2,3‐dihydrophenanthren‐4 (1H)‐one

miltirone

7-Isopropyl-5,6-dimethoxy-1,1-dimethyl-2,3,9,10-tetrahydro-1H-phenanthren-4-one

Refernces

• 1、 Hall III, Clifford A.,Cuppett, Susan L.,Dussault, Pat. "Hydrogen-donating mechanism of rosmariquinone, an antioxidant found in rosemary". . p. 1147 - 1154. Retrieved 1998.