12-Hydroxy-5,8,10,14-heptadectetraenoic acid

Base Information

• Chemical Name: 12-Hydroxy-5,8,10,14-heptadectetraenoic acid
• CAS No.: 74004-31-2
• Molecular Formula: C₁₇H₂₆O₃
• Molecular Weight: 278.392
• Mol file: 74004-31-2.mol

Synonyms:12-HHTE;12-hydroxy-5,8,10,14-heptadectetraenoic acid;12-hydroxy-5,8,10,14-heptadectetraenoic acid, (E,Z,Z,Z)-isomer

Chemical Property of 12-Hydroxy-5,8,10,14-heptadectetraenoic acid

Chemical Property:

• Vapor Pressure: 4.35E-10mmHg at 25°C
• Boiling Point: 452.4°C at 760 mmHg
• Flash Point: 241.5°C
• Density: 1.008g/cm³
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 278.18819469
• Heavy Atom Count: 20
• Complexity: 351

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC=CCC(C=CC=CCC=CCCCC(=O)O)O
• Isomeric SMILES: CC/C=C/CC(/C=C/C=C/C/C=C/CCCC(=O)O)O

Technology Process of 12-Hydroxy-5,8,10,14-heptadectetraenoic acid

There total 15 articles about 12-Hydroxy-5,8,10,14-heptadectetraenoic 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: 63.0%

methyl (S,5Z,8E,10E,14Z)-12-hydroxyheptadeca-5,8,10,14-tetraenoate → (S,5Z,8E,10E,14Z)-12-hydroxyheptadeca-5,8,10,14-tetraenoic acid (74004-31-2)

Guidance literature:

methyl (S,5Z,8E,10E,14Z)-12-hydroxyheptadeca-5,8,10,14-tetraenoate; With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 10h;

In tetrahydrofuran; methanol; water; pH=5;

DOI:10.1039/c6ob02141g

Reference yield:

C12H24O3Si → (S,5Z,8E,10E,14Z)-12-hydroxyheptadeca-5,8,10,14-tetraenoic acid (74004-31-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

2.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C

3.2: 0.5 h / -90 - 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C

5.1: titanium(IV) isopropylate / dichloromethane / 0.5 h / -10 °C

5.2: 6 h / -40 - -18 °C

5.3: 0.5 h / 20 °C

6.1: titanium(IV) isopropylate / dichloromethane / 0.25 h / -30 °C

6.2: 6 h / -30 - -18 °C

6.3: 0.5 h / 20 °C

7.1: triphenylphosphine; 4-nitro-benzoic acid / tetrahydrofuran / 0.25 h / 0 °C

7.2: 1 h / 0 °C

7.3: 0.25 h / 20 °C

8.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.25 h / 0 °C

8.2: 0.5 h / 0 °C

9.1: iodine / diethyl ether / 1 h / 20 °C

10.1: bis-(1,2-dimethylpropyl)borane / tetrahydrofuran / 0.5 h / 0 °C

10.2: 4 h / 20 °C / Inert atmosphere

11.1: lithium hydroxide / methanol; tetrahydrofuran; water / 10 h / 20 °C

11.2: McIlvaine buffer / pH 5

With 1H-imidazole; titanium(IV) isopropylate; n-butyllithium; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; diisopropylamine; triphenylphosphine; lithium hydroxide; 4-nitro-benzoic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; 3.2: |Wittig Olefination / 5.2: |Sharpless Asymmetric Epoxidation / 6.2: |Sharpless Asymmetric Epoxidation / 10.2: |Suzuki-Miyaura Coupling;

DOI:10.1039/c6ob02141g

Reference yield:

(1E,5Z)-1-(trimethylsilyl)octa-1,5-dien-3-ol (127268-91-1) → (S,5Z,8E,10E,14Z)-12-hydroxyheptadeca-5,8,10,14-tetraenoic acid (74004-31-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: titanium(IV) isopropylate / dichloromethane / 0.5 h / -10 °C

1.2: 6 h / -40 - -18 °C

1.3: 0.5 h / 20 °C

2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h

2.2: 1 h / 0 °C

3.1: iodine / diethyl ether / 1 h / 20 °C

4.1: bis-(1,2-dimethylpropyl)borane / tetrahydrofuran / 0.5 h / 0 °C

4.2: 4 h / 20 °C / Inert atmosphere

5.1: lithium hydroxide / methanol; tetrahydrofuran; water / 10 h / 20 °C

5.2: McIlvaine buffer / pH 5

With titanium(IV) isopropylate; n-butyllithium; iodine; bis-(1,2-dimethylpropyl)borane; diisopropylamine; lithium hydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1.2: |Sharpless Asymmetric Epoxidation / 4.2: |Suzuki-Miyaura Coupling;

DOI:10.1039/c6ob02141g

upstream raw materials:

(1E,5Z)-1-(trimethylsilyl)octa-1,5-dien-3-ol

methyl 4-formylbutanoate

(S,Z)-1-((2S,3S)-3-(trimethylsilyl)oxiran-2-yl)hex-3-en-1-ol

(R,1E,5Z)-1-(trimethylsilyl)octa-1,5-dien-3-ol

Refernces