Methyl abietate

Base Information

• Chemical Name: Methyl abietate
• CAS No.: 127-25-3
• Molecular Formula: C21H32 O2
• Molecular Weight: 316.484
• European Community (EC) Number: 204-832-7
• NSC Number: 2141
• UNII: BY54I7IT3L
• DSSTox Substance ID: DTXSID9048190
• Nikkaji Number: J10.051J
• Wikidata: Q27274956
• Metabolomics Workbench ID: 140783
• ChEMBL ID: CHEMBL509586
• Mol file: 127-25-3.mol

Synonyms:abietic acid methyl ester;methyl abietate

Chemical Property of Methyl abietate

Chemical Property:

• Vapor Pressure: 9.9E-07mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: nD20 1.530
• Boiling Point: 403.8°Cat760mmHg
• Flash Point: 192.8°C
• PSA: 26.30000
• Density: 1.02g/cm³
• LogP: 5.29460
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 17μg/L at 25℃
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 316.240230259
• Heavy Atom Count: 23
• Complexity: 556

Purity/Quality:

99.9% ^*data from raw suppliers

METHYL ABIETATE ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C1=CC2=CCC3C(C2CC1)(CCCC3(C)C(=O)OC)C
• Isomeric SMILES: CC(C)C1=CC2=CC[C@@H]3[C@@]([C@H]2CC1)(CCC[C@@]3(C)C(=O)OC)C
• Uses: Methyl Abietate was used as an antiplasticizer for polycarbonates. As a solvent for ester gums, rosin, many synthetic resins, ethyl cellulose, rubber, etc.; in the manufacture of varnish resins; as ingredient in adhesives.

Technology Process of Methyl abietate

There total 22 articles about Methyl abietate 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: 100.0%

abietic acid (514-10-3) + dimethyl sulfate (77-78-1) → methyl abietate (127-25-3)

Guidance literature:

With lithium hydroxide; In N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2009.01.014

Reference yield: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + abietic acid (514-10-3) → methyl abietate (127-25-3)

Guidance literature:

In diethyl ether; at 0 ℃;

DOI:10.1080/00397919908086178

Reference yield: 99.6%

abietic acid (514-10-3) + carbonic acid dimethyl ester (616-38-6) → methyl abietate (127-25-3)

Guidance literature:

With lithium hydroxide monohydrate; In N,N-dimethyl-formamide; at 93 - 100 ℃; Reagent/catalyst; Concentration; Inert atmosphere;

upstream raw materials:

7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydro-phenanthrene-1-carboxylic acid

methyl iodide

diazomethane

(?)-abietic acid

Downstream raw materials:

methyl dehydroabietate

7-keto dehydroabietic acid methyl ester

(1R,4aS)-6-Formyl-1,4a-dimethyl-5-(4-methyl-3-oxo-pentyl)-1,2,3,4,4a,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

9-α-hydroxy-abietic acid methyl ester

Refernces

• 1、 Zhou, Bing,Li, Xiaomei,Feng, Huijin,Li, Yuanchao. "Efficient syntheis of the key intermediate triptophenolide methyl ether for the synthesis of(-)-triptolide". . p. 5396 - 5401. Retrieved 2010.
• 2、 Masnyk, Marek,Ku?mirek, Damian,Trzybiński, Damian,Frelek, Jadwiga. "Research into the oxidation of abietic acid–derived enone with atmospheric oxygen". . p. 437 - 445. Retrieved 2020.
• 3、 Gonzalez, Miguel A.,Correa-Royero, Julieth,Agudelo, Lee,Mesa, Ana,Betancur-Galvis, Liliana. "Synthesis and biological evaluation of abietic acid derivatives". . p. 2468 - 2472. Retrieved 2009.
• 4、 Karlberg,Bohlinder,Boman,Hacksell,Hermansson,Jacobsson,Nilsson. "Identification of 15-hydroperoxyabietic acid as a contact allergen in Portuguese colophony". . p. 42 - 47. Retrieved 1988.
• 5、 Buchbauer, Gerhard,Heneis, Vera M.,Krejci, Viktoria,Talsky, Claudia,Wunderer, Hanneliese. "A New Synthesis of Desmethylambraoxide". . p. 1345 - 1358. Retrieved 1985.
• 6、 Miyajima, Yui,Saito, Yohei,Takeya, Munehisa,Goto, Masuo,Nakagawa-Goto, Kyoko. "Synthesis of 4- epi-Parviflorons A, C, and E: Structure-Activity Relationship Study of Antiproliferative Abietane Derivatives". . . Retrieved 2019/03/19.