Dehydroabietinol

Base Information

• Chemical Name: Dehydroabietinol
• CAS No.: 3772-55-2
• Deprecated CAS: 19426-88-1
• Molecular Formula: C20H30O
• Molecular Weight: 286.458
• European Community (EC) Number: 223-217-4
• UNII: VAD5Q9VDSM
• ChEMBL ID: CHEMBL12799
• DSSTox Substance ID: DTXSID80858748
• Metabolomics Workbench ID: 28516
• Nikkaji Number: J146.752B
• Pharos Ligand ID: ZXG2X48RFUUS
• Wikidata: Q27123468
• Mol file: 3772-55-2.mol

Synonyms:dehydroabietinol

Chemical Property of Dehydroabietinol

Chemical Property:

• Boiling Point: 177 °C
• PKA: 14.94±0.10(Predicted)
• Flash Point: 136.2oC
• PSA: 20.23000
• Density: 0.987±0.06 g/cm3(Predicted)
• LogP: 4.81260
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 286.229665576
• Heavy Atom Count: 21
• Complexity: 376

Purity/Quality:

98%min ^*data from raw suppliers

Dehydroabietinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=CC2=C(C=C1)C3(CCCC(C3CC2)(C)CO)C
• Isomeric SMILES: CC(C)C1=CC2=C(C=C1)[C@]3(CCC[C@@]([C@@H]3CC2)(C)CO)C
• Uses: Dehydroabietinol is the hydroxy derivative of Dehydroabietic Acid (D229085) with antimicrobial activity. Dehydroabietinol also shows fungicidal activity againts wood contaminany fungi.

Technology Process of Dehydroabietinol

There total 14 articles about Dehydroabietinol 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: 99.0%

dehydroabietic acid (1740-19-8) → dehydroabietinol (3772-55-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1039/c9ob00272c

Reference yield: 98.0%

Methyl dehydroabietate (1235-74-1,1757-97-7,2756-34-5,7151-00-0,10178-27-5,10178-29-7,21699-55-8,24035-60-7) → dehydroabietinol (3772-55-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1055/s-2002-33788

Reference yield: 38.0%

abietinol (666-84-2) → dehydroabietinal (13601-88-2) + abieta-7,13-dien-18-al (6704-50-3) + dehydroabietinol (3772-55-2)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 24h; Ambient temperature;

upstream raw materials:

dehydroabietic acid

Methyl dehydroabietate

dehydroabietic acid

abietinol

Downstream raw materials:

Dehydroabietinal

ferruginol

Refernces

• 1、 Fraga, Braulio M.,Hernandez, Melchor G.,Artega, Jose M.,Suarez, Sergio. "The microbiological transformation of the diterpenes dehydroabietanol and teideadiol by Mucor plumbeus". . p. 663 - 668. Retrieved 2003.
• 2、 González-Cardenete, Miguel A.,Zaragozá, Ramón J.. "Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction". . p. 15015 - 15022. Retrieved 2020/04/27.
• 3、 Wang, Dinghai,Mück-Lichtenfeld, Christian,Studer, Armido. "Hydrogen Atom Transfer Induced Boron Retaining Coupling of Organoboronic Esters and Organolithium Reagents". supporting information. p. 14126 - 14130. Retrieved 2019/10/11.