2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoic acid

Base Information

• Chemical Name: 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoic acid
• CAS No.: 103904-74-1
• Molecular Formula: C22H32O3
• Molecular Weight: 344.494
• ChEMBL ID: CHEMBL451725
• DSSTox Substance ID: DTXSID10872876
• Wikidata: Q81978532
• Mol file: 103904-74-1.mol

Synonyms:Anacardic acid diene;103904-74-1;2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoic acid;2-Hydroxy-6-8Z,11Z-pentadecadien-1-yl-benzoic acid;ana-cardic acid;SCHEMBL154719;CHEMBL451725;DTXSID10872876;AKOS040735494;2-Hydroxy-6-(8,11-pentadecadienyl)-(Z,Z)-Benzoic acid;2-Hydroxy-6-(8Z,11Z)-8,11-pentadecadien-1-yl-Benzoic acid

Chemical Property of 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoic acid

Chemical Property:

• Vapor Pressure: 7.09E-11mmHg at 25°C
• Boiling Point: 501.5°Cat760mmHg
• Flash Point: 271.2°C
• Density: 1.027g/cm³
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 344.23514488
• Heavy Atom Count: 25
• Complexity: 400

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCC=CCC=CCCCCCCCC1=C(C(=CC=C1)O)C(=O)O
• Isomeric SMILES: CCC/C=C\C/C=C\CCCCCCCC1=C(C(=CC=C1)O)C(=O)O

Technology Process of 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoic acid

There total 45 articles about 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoic 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: 86.5%

ethyl [8(Z),11(Z)-pentadecadienyl]salicylate (332011-49-1) → 2-hydroxy-6-[(8Z,11Z)-8,11-pentadecadienyl]benzoic acid (103904-74-1)

Guidance literature:

With sodium hydroxide; In ethanol; for 6h; Heating;

DOI:10.1248/cpb.49.18

Reference yield: 69.0%

2-Methoxy-6-((8Z,11Z)-pentadeca-8,11-dienyl)-benzoic acid (173473-61-5) → 2-hydroxy-6-[(8Z,11Z)-8,11-pentadecadienyl]benzoic acid (103904-74-1)

Guidance literature:

With aluminium(III) iodide; (+)-limonene; In carbon disulfide; 1.) r.t., 10 min, 2.) reflux, 30 min;

Reference yield:

5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9) → 2-hydroxy-6-[(8Z,11Z)-8,11-pentadecadienyl]benzoic acid (103904-74-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere; Schlenk technique

2.1: tetrabutyl-ammonium chloride; palladium diacetate; lithium chloride; lithium acetate / N,N-dimethyl acetamide / 3 h / 70 °C / Inert atmosphere; Schlenk technique; Sealed tube

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere; Schlenk technique

3.2: 1 h / -78 - 20 °C / Inert atmosphere; Schlenk technique

4.1: potassium hydroxide / water; 1,4-dioxane / 18 h / 55 °C / Inert atmosphere; Schlenk technique

With pyridine; n-butyllithium; lithium acetate; tetrabutyl-ammonium chloride; palladium diacetate; lithium chloride; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; N,N-dimethyl acetamide; water; 2.1: |Heck Reaction / 3.1: |Wittig Olefination / 3.2: |Wittig Olefination;

DOI:10.1021/acs.orglett.8b02705

upstream raw materials:

2-Methoxy-6-((8Z,11Z)-pentadeca-8,11-dienyl)-benzoic acid

ethyl 2-methoxy-6-[8(Z),11(Z)-pentadecadienyl]benzoate

ethyl [8(Z),11(Z)-pentadecadienyl]salicylate

8-bromooctanol

Downstream raw materials:

6-Pentadecylsalicylic Acid

Refernces

• 1、 Satoh,Takeuchi,Nishimura,Ohta,Tobinaga. "Synthesis of anacardic acids, 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid". . p. 18 - 22. Retrieved 2007/10/03.
• 2、 Zehnter, Reinhard,Gerlach, Hans. "Synthesis of Anacardic Acids". . p. 2209 - 2220. Retrieved 2007/10/03.