Dehydroabietic acid

Base Information

• Chemical Name: Dehydroabietic acid
• CAS No.: 1740-19-8
• Deprecated CAS: 135577-73-0,2501-27-1,35949-24-7,2501-27-1,35949-24-7
• Molecular Formula: C20H28O2
• Molecular Weight: 300.441
• Hs Code.: 29161900
• European Community (EC) Number: 217-102-8
• NSC Number: 2952
• UNII: 0S5XP6S3AU
• DSSTox Substance ID: DTXSID8022163
• Nikkaji Number: J12.735C
• Wikidata: Q27110153
• Pharos Ligand ID: 6696Q4UVMLH7
• Metabolomics Workbench ID: 28511
• ChEMBL ID: CHEMBL12850
• Mol file: 1740-19-8.mol

Synonyms:dehydroabietic acid

Chemical Property of Dehydroabietic acid

Chemical Property:

• Vapor Pressure: 5.53E-08mmHg at 25°C
• Melting Point: 174-176 °C
• Refractive Index: 1.54
• Boiling Point: 425.085 °C at 760 mmHg
• PKA: 4.66±0.40(Predicted)
• Flash Point: 202.504 °C
• PSA: 37.30000
• Density: 1.059 g/cm³
• LogP: 4.90490
• Storage Temp.: ?20°C
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 300.208930132
• Heavy Atom Count: 22
• Complexity: 443

Purity/Quality:

98%min ^*data from raw suppliers

Dehydroabietic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 25-50
• Safety Statements: 45-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: other linear non-peptide (Diterpenoid)
• Canonical SMILES: CC(C)C1=CC2=C(C=C1)C3(CCCC(C3CC2)(C)C(=O)O)C
• Isomeric SMILES: CC(C)C1=CC2=C(C=C1)[C@]3(CCC[C@@]([C@@H]3CC2)(C)C(=O)O)C
• Uses: Dehydroabietic Acid is a resin acid found commonly in rosin. Dehydroabietic Acid is used in rosin-type nucleating agent for polypropylene (PP). Dehydroabietic Acid is used commonly in the synthesis of surfactants, antioxidants and chiral catalysts.

Technology Process of Dehydroabietic acid

There total 34 articles about Dehydroabietic acid 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%

(?)-abietic acid (514-10-3,4711-77-7,5618-76-8,17817-95-7,24563-90-4) → dehydroabietic acid (1740-19-8)

Guidance literature:

With palladium 10% on activated carbon; In para-xylene; at 148 ℃; for 48h;

DOI:10.1021/ol4003652

Reference yield: 88.0%

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) → dehydroabietic acid (1740-19-8)

Guidance literature:

With Me₂AlTeMe; In toluene; at 23 ℃; for 10h;

DOI:10.1016/j.tetlet.2005.05.003

Reference yield: 62.0%

(1S,4aS,10aS)-7-isopropyl-1,4a-dimethyl-1-(2-methylprop-1-enyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene (1527482-56-9) → dehydroabietic acid (1740-19-8)

Guidance literature:

With potassium permanganate; sodium periodate; water; sodium carbonate; In tert-butyl alcohol; at 23 ℃; for 12h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja4125093

upstream raw materials:

abietic acid

methyl abietate

maleopimaric acid

dodecaethylene glycol

Downstream raw materials:

N-((1R,4aS,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-yl)-benzamide

Retene

(2-Methyl-6-methylene-3-oxo-cyclohexyl)-acetic acid methyl ester

dehydroabietinol

Refernces

• 1、 Persson, Margareta,Stenius, Per,Stroem, Goeran,Oedberg, Lars,Bolmgren, Ingmari,et al.. "Solubilization, Micellization, and Phase Equilibria of Polyoxyethylene Derivatives of Dehydroabietic Acid". . p. 1557 - 1560. Retrieved 1980.
• 2、 Jeger,Duerst,Buechi. "-". . p. 1853,1857. Retrieved 1947.
• 3、 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.
• 4、 Surendra, Karavadhi,Rajendar, Goreti,Corey. "Useful catalytic enantioselective cationic double annulation reactions initiated at an internal π-bond: Method and applications". . p. 642 - 645. Retrieved 2014/02/14.