3-hydroxyheptadecanoic Acid

Base Information

• Chemical Name: 3-hydroxyheptadecanoic Acid
• CAS No.: 40165-89-7
• Molecular Formula: C17H34 O3
• Molecular Weight: 286.455
• DSSTox Substance ID: DTXSID70960607
• Nikkaji Number: J297.090B
• Mol file: 40165-89-7.mol

Synonyms:3-hydroxyheptadecanoic Acid;40165-89-7;Heptadecanoic acid, 3-hydroxy-;3-hydroxy Heptadecanoic Acid;SCHEMBL311718;rac-3-Hydroxyheptadecanoic Acid;DTXSID70960607;MFCD02259049;AKOS030254243

Chemical Property of 3-hydroxyheptadecanoic Acid

Chemical Property:

• Vapor Pressure: 9.18E-09mmHg at 25°C
• Boiling Point: 418.7°C at 760 mmHg
• Flash Point: 221.2°C
• PSA: 57.53000
• Density: 0.949g/cm³
• LogP: 4.91320
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 286.25079494
• Heavy Atom Count: 20
• Complexity: 216

Purity/Quality:

99% ^*data from raw suppliers

rac-3-HydroxyheptadecanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCC(CC(=O)O)O
• Description: 3-hydroxy Heptadecanoic acid is a hydroxylated fatty acid. It is a component of LPS in several species of Gram-negative bacteria. Levels of 3-hydroxy heptadecanoic acid are decreased in the feces of patients with Crohn’s disease. [Matreya, LLC. Catalog No. 1741]
• Uses: 3-Hydroxyheptadecanoic acid is a fatty acid that is found in periodontally diseased human teeth, especially smokers. 3-Hydroxyheptadecanoic acid is also found in the polar lipods of the edible alga Grateloupia turuturu.

Technology Process of 3-hydroxyheptadecanoic Acid

There total 3 articles about 3-hydroxyheptadecanoic 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:

lipopolysaccharide from Sinorhizobium fredii HH103, rkpA → 3-hydroxytetradecanoic acid (1961-72-4,3422-31-9) + 3-hydroxydodecanoic acid (1883-13-2,53941-38-1) + 3-hydroxytridecanoic acid (32602-69-0) + 3-hydroxypentadecanoic acid (32602-70-3) + β-hydroxypalmitic acid (928-17-6,2398-34-7,20595-04-4,83780-74-9) + 3-hydroxy-heptadecanoic acid (40165-89-7) + 3-hydroxyoctadecanoic acid (17773-30-7) + 3-hydroxy-nonadecanoic acid (40165-90-0) + 27-hydroxy-octacosanoic acid (121822-56-8) + 29-hydroxytriacontanoic acid

Guidance literature:

lipopolysaccharide from Sinorhizobium fredii HH₁₀₃, rkpA; With hydrogenchloride; water; at 100 ℃; for 4h;

With water; sodium hydroxide; at 100 ℃; for 0.5h;

DOI:10.1074/jbc.ra120.013393

Reference yield:

lipopolysaccharide from Sinorhizobium fredii HH103, rkpM → 3-hydroxytetradecanoic acid (1961-72-4,3422-31-9) + 3-hydroxydodecanoic acid (1883-13-2,53941-38-1) + 3-hydroxytridecanoic acid (32602-69-0) + 3-hydroxypentadecanoic acid (32602-70-3) + β-hydroxypalmitic acid (928-17-6,2398-34-7,20595-04-4,83780-74-9) + 3-hydroxy-heptadecanoic acid (40165-89-7) + 3-hydroxyoctadecanoic acid (17773-30-7) + 3-hydroxy-nonadecanoic acid (40165-90-0) + 27-hydroxy-octacosanoic acid (121822-56-8) + 29-hydroxytriacontanoic acid

Guidance literature:

lipopolysaccharide from Sinorhizobium fredii HH₁₀₃, rkpM; With hydrogenchloride; water; at 100 ℃; for 4h;

With water; sodium hydroxide; at 100 ℃; for 0.5h;

DOI:10.1074/jbc.ra120.013393

Reference yield:

heptadecanoic acid (506-12-7) → 1-Hexadecene (629-73-2) + 3-hydroxy-heptadecanoic acid (40165-89-7)

Guidance literature:

With ethylenediaminetetraacetic acid; recombinant Jeotgalicoccussp_. ATCC 8456 P₄₅₀ fatty acid decarboxylase; Flavin mononucleotide; In aq. buffer; at 25 ℃; for 2h; pH=7.5; Irradiation; Enzymatic reaction;

DOI:10.1039/c4cc07276f

upstream raw materials:

heptadecanoic acid

Downstream raw materials:

benzyl N-(3-hydroxy-heptadecanoyl)glycine

benzyl N-[3-(14-methyl-11-pentadecenoyloxy)heptadecenoyl]glycinee

benzyl N-[3-(21-methyl-11-tridecenoyloxy)heptadecanoyl]chloride

benzyl N-[3-(13-methyl-11-tetradecenoyloxy)heptadecanoyl]glycine

Refernces

• 1、 Zachos, Ioannis,Ga?meyer, Sarah Katharina,Bauer, Daniel,Sieber, Volker,Hollmann, Frank,Kourist, Robert. "Photobiocatalytic decarboxylation for olefin synthesis". supporting information. p. 1918 - 1921. Retrieved 2015/02/05.