3-Hydroxydecanoic acid

Base Information

• Chemical Name: 3-Hydroxydecanoic acid
• CAS No.: 14292-26-3
• Molecular Formula: C₁₀H₂₀O₃
• Molecular Weight: 188.267
• Hs Code.: 2918199090
• UNII: IGH24U4AMF
• DSSTox Substance ID: DTXSID40864486
• Nikkaji Number: J19.953B
• Wikipedia: Myrmicacin
• Wikidata: Q15425812
• Pharos Ligand ID: PSZMMM5N12FX
• Metabolomics Workbench ID: 1359
• ChEMBL ID: CHEMBL4448230
• Mol file: 14292-26-3.mol

Synonyms:3-HDA;3-hydroxy-decanoic acid;3-hydroxydecanoic acid;3-hydroxydecanoic acid, (3R)-;beta-hydroxydecanoic acid;myrmicacin;myrmicacin monosodium (+-)-isomer;myrmicacin, (+-)-isomer;myrmicacin, (R)-isomer

Chemical Property of 3-Hydroxydecanoic acid

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 3.03E-05mmHg at 25°C
• Melting Point: 47-48 °C
• Refractive Index: 1.464
• Boiling Point: 318.2 °C at 760 mmHg
• PKA: 4.39±0.10(Predicted)
• Flash Point: 160.5 °C
• PSA: 57.53000
• Density: 1.011 g/cm³
• LogP: 2.18250
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 188.14124450
• Heavy Atom Count: 13
• Complexity: 134

Purity/Quality:

99% ^*data from raw suppliers

3-HydroxydecanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCC(CC(=O)O)O
• Description: 3-hydroxy Decanoic acid is a hydroxy fatty acid and the predominant monomer in methyl-branched poly(3-hydroxyalkanoate) (PHA) polymers produced by P. putida CA-3. It is present in LPS from the H. pylori strain SS1 and in the lipid A component of clinical isolates of P. aeruginosa isolated from patients with cystic fibrosis but not the environment or patients with other conditions. 3-hydroxy Decanoic acid inhibits mitotic progression of O. virens pollens via impairment of plasma membrane function. It also induces a reversible shape change of the membrane crenation in human erythrocytes. [Matreya, LLC. Catalog No. 1727]

Technology Process of 3-Hydroxydecanoic acid

There total 21 articles about 3-Hydroxydecanoic 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: 93.0%

methyl 3-hydroxydecanoate (62675-82-5) → 3-hydroxydecanoic acid (5561-87-5,19525-80-5,19526-23-9,33044-91-6,14292-26-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 12h;

DOI:10.1016/j.bioorg.2019.03.023

Reference yield: 90.0%

ethyl (R/S)-3-hydroxy-decanoate (6071-25-6) → 3-hydroxydecanoic acid (5561-87-5,19525-80-5,19526-23-9,33044-91-6,14292-26-3)

Guidance literature:

ethyl (R/S)-3-hydroxy-decanoate; With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 12h;

With hydrogenchloride; In tetrahydrofuran; water;

Reference yield: 85.0%

Iodoacetic acid (64-69-7) + Octanal (124-13-0) → 3-hydroxydecanoic acid (5561-87-5,19525-80-5,19526-23-9,33044-91-6,14292-26-3)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 25 ℃; for 3.5h;

DOI:10.1021/jo060118j

upstream raw materials:

methyl 3-oxodecanoate

Octanal

ethyl bromoacetate

acetic acid

Downstream raw materials:

decanoic acid, 3-trimethylsilyloxy, trimethylsilyl ester

benzyl (±)-3-hydroxydecanoate

nonan-2-ol

1-decanoic acid

Refernces

• 1、 Concellon, Jose M.,Concellon, Carmen. "Aldol-type reactions of unmasked iodoacetic acid with carbonyl compounds promoted by samarium diiodide: Efficient synthesis of carboxylic 3-hydroxyacids and their derivatives". . p. 4428 - 4432. Retrieved 2006.
• 2、 Hammerer, Lucas,Friess, Michael,Cerne, Jeyson,Fuchs, Michael,Steinkellner, Georg,Gruber, Karl,Vanhessche, Koenraad,Plocek, Thomas,Winkler, Christoph K.,Kroutil, Wolfgang. "Controlling the Regioselectivity of Fatty Acid Hydroxylation (C10) at α- and β-Position by CYP152A1 (P450Bsβ) Variants". . p. 5642 - 5649. Retrieved 2019.
• 3、 Komatsu, Hidekazu,Shirakawa, Takashi,Uchiyama, Takeo,Hoshino, Tsutomu. "Chemical structure of cichorinotoxin, a cyclic lipodepsipeptide that is produced by Pseudomonas cichorii and causes varnish spots on lettuce". . p. 299 - 309. Retrieved 2019/02/20.