Abietic acid

Base Information

• Chemical Name: Abietic acid
• CAS No.: 514-10-3
• Deprecated CAS: 72452-62-1,118817-23-5,37271-91-3,39390-87-9,68153-42-4,8050-10-0,8050-14-4,8052-47-9,1481684-92-7,2415627-68-6,2701526-14-7
• Molecular Formula: C20H30O2
• Molecular Weight: 302.457
• Hs Code.: 29162090
• European Community (EC) Number: 232-475-7,233-584-2,208-178-3
• ICSC Number: 0358
• NSC Number: 154789,25149
• UNII: V3DHX33184
• DSSTox Substance ID: DTXSID7022047
• Nikkaji Number: J10.135D
• Wikipedia: Abietic_acid
• Wikidata: Q321068
• Metabolomics Workbench ID: 28507
• ChEMBL ID: CHEMBL71893
• Mol file: 514-10-3.mol

Synonyms:abietic acid;abietic acid, 2-aminoethanol;abietic acid, ammonium salt;abietic acid, barium salt;abietic acid, calcium salt;abietic acid, cobalt salt;abietic acid, copper salt;abietic acid, palladium (+2) salt;abietic acid, potassium salt;abietic acid, sodium salt;abietic acid, strontium salt;abietic acid, zinc salt;sylvic acid

Chemical Property of Abietic acid

Chemical Property:

• Appearance/Colour: yellow resinous powder, crystals or chunks
• Vapor Pressure: 5.96E-09mmHg at 25°C
• Melting Point: 139-142 °C(lit.)
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 439.5 °C at 760 mmHg
• PKA: pK1:7.62 (25°C)
• Flash Point: 208.1 °C
• PSA: 37.30000
• Density: 1.06 g/cm³
• LogP: 5.20620
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Soluble in alcohols, acetone and ethers
• Water Solubility.: Soluble in acetone, petroleum ether, diethyl ether and ethanol. Insoluble in water.
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 302.224580195
• Heavy Atom Count: 22
• Complexity: 542

Purity/Quality:

98% ^*data from raw suppliers

Abietic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36/37/38-50-50/53
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: UVCB,Biological Agents -> Rosin and Derivatives,other linear non-peptide (Diterpenoid)
• Canonical SMILES: CC(C)C1=CC2=CCC3C(C2CC1)(CCCC3(C)C(=O)O)C
• Isomeric SMILES: CC(C)C1=CC2=CC[C@@H]3[C@@]([C@H]2CC1)(CCC[C@@]3(C)C(=O)O)C
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered or as fumes.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma.
• Description: Abietic acid is probably a major allergen of colophony, by way of oxidation products. Its detection in a material indicates that allergenic components of colophony are present.
• Uses: Abietic Acid is the primary component of resin acid found commonly in rosin. Abietic Acid exhibited potent testosterone 5α-reductase inhibitory activity in vitro. manufacture of esters (ester gums), e.g., methyl ester, vinyl and glyceryl esters for use in lacquers and varnishes; manufacture of "metal resinates", soaps, plastics, and paper sizes; assists growth of lactic and butyric acid bacteria; component in tall oil used as deodorizing agent in cooling fluids; major component of rosin used in the production of varnishes, printing inks, paper, soldering fluxes, greases, cutting fluids, glue tackifiers, adhesives, surface coatings, polish, shoes, insulations, waxes, cosmetics (mascara, rouge, eye shadow), topical medicaments, violin bow rosin, day, athletic grip aid, pine oil deansers; component in dental impression materials and periodontal packings Abietic acid is used to make ester gums in lacquers, varnishes and soaps. It is also used in metal resonates and plastics. Further, it is utilized in musical instruments to make them less slippery. It acts as a precursor to natural product synthesis. In addition to this, it is used to depackage integrated circuits from their epoxy coatings.

Technology Process of Abietic acid

There total 35 articles about Abietic 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: 85.0%

methyl abietate (127-25-3) → abietic acid (514-10-3)

Guidance literature:

With Me₂AlTeMe; In toluene; at 23 ℃; for 8h;

DOI:10.1016/j.tetlet.2005.05.003

Reference yield: 3.0%

levopimaric acid (79-54-9) → dehydroabietic acid (1740-19-8) + abietic acid (514-10-3) + <1R-(1α,4aβ,4bα,6α,10aα)>-1,2,3,4,4a,4b,5,6,10,10a-Decahydro-6-hydroxy-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrencarbonsaeure-methylester (3484-53-5) + 15-hydroxydehydroabietic acid methyl ester (29461-23-2)

Guidance literature:

In dichloromethane; for 720h; Product distribution; autoxidation, daylight; partially identification after esterification with diazomethane;

Reference yield:

→ abietic acid (514-10-3)

Guidance literature:

With hydrogenchloride; ethanol;

DOI:10.3758/BF03195283

upstream raw materials:

methanesulfonic acid

ethanol

neoabietic acid

levopimaric acid

Downstream raw materials:

ethyl abietate

abieta-7,13-dien-18-oic acid benzyl ester

6-[2-((1R)-2c,6c-dimethyl-6t-vinyl-2t-carboxy-cyclohexyl-(r))-ethyl]-4-isopropyl-phthalic acid

Retene

Refernces

• 1、 Ritchie,McBurney. "-". . p. 1197,1198. Retrieved 1950.
• 2、 Bardyschew et al.. "". . p. 1147; engl. Ausg. S. 1091. Retrieved 1961.
• 3、 Reddy, B.V. Subba,Reddy, Leleti Rajender,Corey. "Dimethylaluminum methyltellurate, a new reagent for the cleavage of hindered methyl esters under exceptionally mild conditions by a novel mechanism". . p. 4589 - 4593. Retrieved 2007/10/03.
• 4、 Paul, Soumendu,Schmidt, Richard R.. "A new base mediated method for the cleavage of tert-butyl esters". . p. 1107 - 1108. Retrieved 2007/10/03.