9-Hydroxyhexadecanoic acid

Base Information

• Chemical Name: 9-Hydroxyhexadecanoic acid
• CAS No.: 17833-52-2
• Molecular Formula: C₁₆H₃₂O₃
• Molecular Weight: 272.428
• DSSTox Substance ID: DTXSID301311269
• Nikkaji Number: J297.082A
• Mol file: 17833-52-2.mol

Synonyms:9-Hydroxyhexadecanoic acid;9-Hydroxypalmitic acid;17833-52-2;Hexadecanoic acid, 9-hydroxy-;SCHEMBL7081331;DTXSID301311269;G65851

Chemical Property of 9-Hydroxyhexadecanoic acid

Chemical Property:

• Vapor Pressure: 2.56E-08mmHg at 25°C
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 272.23514488
• Heavy Atom Count: 19
• Complexity: 204

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCC(CCCCCCCC(=O)O)O

Technology Process of 9-Hydroxyhexadecanoic acid

There total 10 articles about 9-Hydroxyhexadecanoic 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%

(S)-9-acetoxyhexadecanoic acid → (S)-9-hydroxyhexadecanoic acid (17833-52-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 16h;

DOI:10.1002/ejoc.201801881

Reference yield:

1-hexadecylcarboxylic acid (57-10-3) → 11-hydroxyhexadecanoic acid (502-75-0) + 10-hydroxy-hexadecanoic acid (3422-30-8,23048-75-1,23048-82-0) + 9-hydroxyhexadecanoic acid (17833-52-2)

Guidance literature:

With cytochrome P₄₅₀ BM-3 enzyme mutant 9-10A-F₈₇A; Enzymatic reaction;

Reference yield:

(S)-16-(benzyloxy)hexadecan-8-yl acetate → (S)-9-hydroxyhexadecanoic acid (17833-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 16 h

2: Jones reagent / acetone / 1 h / 0 °C

3: lithium hydroxide / tetrahydrofuran; water / 16 h / 20 °C

With Jones reagent; palladium 10% on activated carbon; hydrogen; lithium hydroxide; In tetrahydrofuran; methanol; water; acetone;

DOI:10.1002/ejoc.201801881

upstream raw materials:

1-hexadecylcarboxylic acid

10-benzyloxy-1-decanal

10-(benzyloxy)decane-1-ol

Refernces

• 1、 -. "ALKANE OXIDATION BY MODIFIED HYDROXYLASES". Paragraph 0342. . Retrieved 2016/02/16.