(3R)-3-Hydroxydodecanoic acid

Base Information

• Chemical Name: (3R)-3-Hydroxydodecanoic acid
• CAS No.: 28254-78-6
• Molecular Formula: C12H24O3
• Molecular Weight: 216.321
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID30415603
• Nikkaji Number: J1.159.652E
• Wikidata: Q27097164
• Metabolomics Workbench ID: 1435
• ChEMBL ID: CHEMBL1233457
• Mol file: 28254-78-6.mol

Synonyms:(3R)-3-Hydroxydodecanoic acid;(R)-3-hydroxydodecanoic acid;28254-78-6;D-3-Hydroxydodecanoic acid;D-(-)-3-Hydroxydodecanoic acid;3R-hydroxy-dodecanoic acid;CHEBI:43197;Dodecanoic acid, 3-hydroxy-, (R)-;Dodecanoic acid, 3-hydroxy-, D-(-)- (8CI);HXD;3-OH-DODECANOATE;(R)-3-OH lauric acid;(R)-beta-OH lauric acid;(R)-3-hydroxylauric acid;(3R)-3-hydroxylauric acid;(R)-3-hydroxydodecanoicacid;(R)-3-OH dodecanoic acid;(R)-beta-hydroxylauric acid;(R)-beta-OH dodecanoic acid;SCHEMBL1268124;(R)-beta-hydroxydodecanoic acid;CHEMBL1233457;DTXSID30415603;LMFA01050251;DB07930;Q27097164

Chemical Property of (3R)-3-Hydroxydodecanoic acid

Chemical Property:

• PSA: 57.53000
• LogP: 2.96270
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 216.17254462
• Heavy Atom Count: 15
• Complexity: 157

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCCC(CC(=O)O)O
• Isomeric SMILES: CCCCCCCCC[C@H](CC(=O)O)O

Technology Process of (3R)-3-Hydroxydodecanoic acid

There total 45 articles about (3R)-3-Hydroxydodecanoic 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: 97.0%

ethyl (R)-3-hydroxy-dodecanoate (893842-45-0) → (3R)-(-)-3-Hydroxydodecanoic acid (28254-78-6,53941-38-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 3h;

DOI:10.1016/j.bmcl.2006.04.029

Reference yield: 81.0%

(R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxydodecan-1-one → (3R)-(-)-3-Hydroxydodecanoic acid (28254-78-6,53941-38-1)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 0 - 20 ℃; for 10h; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.04.037

Reference yield: 77.0%

(R)-3-hydroxydodecanenitrile (922527-71-7) → (3R)-(-)-3-Hydroxydodecanoic acid (28254-78-6,53941-38-1)

Guidance literature:

With dihydrogen peroxide; sodium hydroxide; In methanol; water; for 20h; Reflux;

DOI:10.1039/c6ob01233g

upstream raw materials:

caprinaldehyde

bromoacetic acid tert-butyl ester

(3R)-acetoxy-pentanedioic acid monomethyl ester

nonanoic acid

Downstream raw materials:

(R)-β-hydroxydodecanoic acid methyl ester

fellutamide B

(S)-methyl 3-hydroxydodecanoate

Refernces

• 1、 Vining,L.C.,Taber,W.A.. "-". . p. 1579 - 1584. Retrieved 1962.
• 2、 Bourboula, Asimina,Limnios, Dimitris,Kokotou, Maroula G.,Mountanea, Olga G.,Kokotos, George. "Enantioselective organocatalysis-based synthesis of 3-hydroxy fatty acids and fatty γ-lactones". . . Retrieved 2019/06/10.
• 3、 -. "Correction: Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation (Organic and Biomolecular Chemistry (2016) 14 (8367-8375)". . p. 9159 - 9159. Retrieved 2016/10/11.