2-HYDROXYHEXADECANOIC ACID

Base Information

• Chemical Name: 2-HYDROXYHEXADECANOIC ACID
• CAS No.: 10067-06-8
• Molecular Formula: C₁₆H₃₂O₃
• Molecular Weight: 272.428
• Mol file: 10067-06-8.mol

Synonyms:2-HYDROXY C16:0 ACID;(+/-)-2-HYDROXYHEXADECANOIC ACID;2-HYDROXYHEXADECANOIC ACID;2-HYDROXYPALMITIC ACID;DL-ALPHA-HYDROXYPALMITIC ACID;HYDROXYPALMITIC ACID, 2-

Chemical Property of 2-HYDROXYHEXADECANOIC ACID

Chemical Property:

• Vapor Pressure: 2.89E-08mmHg at 25°C
• Boiling Point: 405.5°C at 760 mmHg
• Flash Point: 213.2°C
• PSA: 57.53000
• Density: 0.955g/cm³
• LogP: 4.52310
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Hydroxyhexadecanoic acid ≥98% (capillary GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Hydroxyhexadecanoic Acid is used in the investigation of role of hypoxia in mechanism of action of elisidepsin which reduces drug efficiency by inhibiting hydroxylation and altering structure of lipid rafts in human SKBR-3, MCF-7, MDA-MB-453 cell lines. Also used in the studies on the antiviral activity of hydroxy fatty acids.

Technology Process of 2-HYDROXYHEXADECANOIC ACID

There total 47 articles about 2-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: 89.0%

methyl (R)-2-hydroxyhexadecanoate (16742-51-1,78330-57-1,89301-98-4,36451-47-5) → (R)-(-)-2-hydroxyhexadecanoic acid (16452-51-0,10067-06-8)

Guidance literature:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 20 ℃; for 5h;

DOI:10.1039/b920285d

Reference yield:

1-hexadecylcarboxylic acid (57-10-3) → (R)-(-)-2-hydroxyhexadecanoic acid (16452-51-0,10067-06-8) + palmitic acid (1002-84-2) + 2-oxo-hexadecanoic acid (2570-24-3) + (R)-2-hydroperoxyhexadecanoic acid

Guidance literature:

With oxygen; In dimethyl sulfoxide; at 5 ℃; for 0.5h; Title compound not separated from byproducts; Triton X-100, phosphate buffer (pH 6.0), crude enzyme from Ulva pertusa;

DOI:10.1016/S0040-4039(98)02547-7

Reference yield:

2-acetoxy-hexadecanoic acid ethyl ester (260055-66-1) → 2-hydroxypalmitic acid (764-67-0,10067-06-8)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1016/S0960-894X(99)00580-6

upstream raw materials:

methyl (R)-2-hydroxyhexadecanoate

vinyl acetate

2-hydroxypalmitic acid

(R)-2-aminohexadecanoic acid

Downstream raw materials:

methyl (R)-2-hydroxyhexadecanoate

(R)-(-)-2-hydroxyhexadecanoic acid

(S)-(+)-2-acetoxyhexadecanoic acid

D(R)-α-acetoxypalmitic acid

Refernces

• 1、 Armbruster, Julia,Steinmassl, Mathilde,Müller Bogotá, Christina A.,Berg, Gabriele,Nidetzky, Bernd,Dennig, Alexander. "P450Jα: A New, Robust and α-Selective Fatty Acid Hydroxylase Displaying Unexpected 1-Alkene Formation". . p. 15910 - 15921. Retrieved 2020/10/29.
• 2、 Dennig, Alexander,Blaschke, Fabio,Gandomkar, Somayyeh,Tassano, Erika,Nidetzky, Bernd. "Preparative Asymmetric Synthesis of Canonical and Non-canonical a-amino Acids through Formal Enantioselective Biocatalytic Amination of Carboxylic Acids". supporting information. p. 1348 - 1358. Retrieved 2019/10/28.