2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid

Base Information

• Chemical Name: 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid
• CAS No.: 103904-73-0
• Molecular Formula: C22H30 O3
• Molecular Weight: 342.478
• DSSTox Substance ID: DTXSID70872877
• Wikidata: Q527648
• ChEMBL ID: CHEMBL455368
• Mol file: 103904-73-0.mol

Synonyms:CHEMBL455368;2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid;103904-73-0;2-hydroxy-6-(8Z,11Z)-8,11,14-pentadecatrien-1-yl-benzoicacid;2-Hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trien-1-yl]benzoic acid;(15:3)-Anacardic acid;2-hydroxy-6-((8Z,11Z)-pentadeca-8,11,14-trienyl)benzoic acid;MEGxp0_000812;SCHEMBL4142096;ACon1_001118;DTXSID70872877;CHEBI:183726;2-Pentadecyl-6-hydroxybenzoic acid;BDBM50292429;LMPK15040001;AKOS040736422;NCGC00169660-01;NCGC00169660-02;Q527648;(15:3)-Anacardic acid, >=85% (LC/MS-ELSD);BRD-K93380348-001-01-8;6[8''(Z ),11''(Z ),14''-pentadecatrienyl]salicylicacid

Chemical Property of 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid

Chemical Property:

• Vapor Pressure: 1.32E-11mmHg at 25°C
• Boiling Point: 519.2°C at 760 mmHg
• Flash Point: 281.9°C
• Density: 1.041g/cm³
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 342.21949481
• Heavy Atom Count: 25
• Complexity: 425

Purity/Quality:

≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid

There total 12 articles about 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]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: 88.5%

ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate (173446-84-9) → 6-(8(Z),11(Z),14-pentadecatrienyl)salicylic acid (103904-73-0)

Guidance literature:

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

DOI:10.1248/cpb.49.18

Reference yield:

8-bromooctanol (50816-19-8) → 6-(8(Z),11(Z),14-pentadecatrienyl)salicylic acid (103904-73-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 90.2 percent / SOCl₂; pyridine / benzene / 7 h / 75 °C

2.1: BuLi; HMPA / hexane; tetrahydrofuran / 0.5 h / 0 °C

2.2: 89.4 percent / hexane; tetrahydrofuran / 1 h / 0 °C

3.1: 77.3 percent / hydroquinone; aq. H₃PO₄ / dioxane / 4.5 h / 100 °C

4.1: 60.8 percent / methanol / 1.5 h / 20 °C

5.1: 79.5 percent / Ag₂O / CH₂Cl₂ / 24 h / 20 °C

6.1: 95.4 percent / NaI / acetone / 24 h / Heating

7.1: 82.4 percent / NaHCO₃; DMSO / 11 h / 90 °C

8.1: BuLi / hexane; tetrahydrofuran / 1 h / 20 °C

8.2: 69.3 percent / tetrahydrofuran / 0.5 h / 20 °C

9.1: 75 percent / BBr₃ / CH₂Cl₂ / 1 h / 20 °C

10.1: 88.5 percent / 10 percent NaOH / ethanol / 6 h / Heating

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; n-butyllithium; thionyl chloride; phosphoric acid; boron tribromide; sodium hydrogencarbonate; dimethyl sulfoxide; hydroquinone; sodium iodide; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; acetone; benzene; 9.2: Wittig reaction;

DOI:10.1248/cpb.49.18

Reference yield:

1-bromo-8-chloro-octane (28598-82-5) → 6-(8(Z),11(Z),14-pentadecatrienyl)salicylic acid (103904-73-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: BuLi; HMPA / hexane; tetrahydrofuran / 0.5 h / 0 °C

1.2: 89.4 percent / hexane; tetrahydrofuran / 1 h / 0 °C

2.1: 77.3 percent / hydroquinone; aq. H₃PO₄ / dioxane / 4.5 h / 100 °C

3.1: 60.8 percent / methanol / 1.5 h / 20 °C

4.1: 79.5 percent / Ag₂O / CH₂Cl₂ / 24 h / 20 °C

5.1: 95.4 percent / NaI / acetone / 24 h / Heating

6.1: 82.4 percent / NaHCO₃; DMSO / 11 h / 90 °C

7.1: BuLi / hexane; tetrahydrofuran / 1 h / 20 °C

7.2: 69.3 percent / tetrahydrofuran / 0.5 h / 20 °C

8.1: 75 percent / BBr₃ / CH₂Cl₂ / 1 h / 20 °C

9.1: 88.5 percent / 10 percent NaOH / ethanol / 6 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; n-butyllithium; phosphoric acid; boron tribromide; sodium hydrogencarbonate; dimethyl sulfoxide; hydroquinone; sodium iodide; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; acetone; 8.2: Wittig reaction;

DOI:10.1248/cpb.49.18

upstream raw materials:

ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate

8-bromooctanol

1-bromo-8-chloro-octane

ethyl 6-(7-formylheptyl)-2-methoxybenzoate

Downstream raw materials:

2-(azidomethyl)-1-methoxy-3-pentadecylbenzene

Refernces