(R)-3-Hydroxytetradecanoic acid

Base Information

• Chemical Name: (R)-3-Hydroxytetradecanoic acid
• CAS No.: 28715-21-1
• Molecular Formula: C14H28 O3
• Molecular Weight: 244.375
• Hs Code.: 2918199090
• European Community (EC) Number: 631-127-5
• UNII: R7C245Y68X
• DSSTox Substance ID: DTXSID001305047
• Nikkaji Number: J784.832C
• Wikidata: Q27093717
• Metabolomics Workbench ID: 1468
• ChEMBL ID: CHEMBL1232858
• Mol file: 28715-21-1.mol

Synonyms:(R)-3-Hydroxytetradecanoic acid;(R)-3-Hydroxymyristic acid;28715-21-1;(3R)-3-Hydroxytetradecanoic acid;(R)-(-)-3-Hydroxytetradecanoic acid;D-(-)-beta-Hydroxymyristic acid;D-3-Hydroxyte;(r)-3-hydroxy myristic acid;Tetradecanoic acid, 3-hydroxy-, (3R)-;CHEBI:42539;(3R)-hydroxymyristic acid;(-)-3-hydroxymyristic acid;3R-hydroxy-tetradecanoic acid;3-Hydroxymyristic acid, (-)-;CHEMBL1232858;3-Hydroxymyristic acid, (3R)-;(R)-3-Hydroxy-tetradecanoic acid;R7C245Y68X;(3R)-3-hydroxy-tetradecanoic acid;Tetradecanoic acid, 3-hydroxy-, (R)-;Tetradecanoic acid, 3-hydroxy-, D-(-)-;3-HYDROXY-MYRISTIC ACID;R-(3)-HYDROXYMYRISTIC ACID;UNII-R7C245Y68X;3-HTA;(3R)-3-hydroxymyristic acid;SCHEMBL142894;(R)-3-hydroxy tetradecanoic acid;ATRNZOYKSNPPBF-CYBMUJFWSA-N;DTXSID001305047;AMY25629;BDBM50511000;LMFA01050322;MFCD00211333;DB02767;BP-29865;D-(-)-.BETA.-HYDROXYMYRISTIC ACID;CS-0333355;C22001;J-017216;Q27093717

Chemical Property of (R)-3-Hydroxytetradecanoic acid

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 3.16E-07mmHg at 25°C
• Melting Point: 71-72°C
• Boiling Point: 376.9°C at 760 mmHg
• PKA: 4.38±0.10(Predicted)
• Flash Point: 195.9°C
• PSA: 57.53000
• Density: 0.969g/cm³
• LogP: 3.74290
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Diethyl Ether (Slightly), Eth
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 12
• Exact Mass: 244.20384475
• Heavy Atom Count: 17
• Complexity: 180

Purity/Quality:

99%, ^*data from raw suppliers

3-Hydroxytetradecanoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(CC(=O)O)O
• Isomeric SMILES: CCCCCCCCCCC[C@H](CC(=O)O)O
• Uses: One of two major component of bacterial Lipid A .

Technology Process of (R)-3-Hydroxytetradecanoic acid

There total 28 articles about (R)-3-Hydroxytetradecanoic 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: 100.0%

methyl 3-oxotetradecanoate (22348-97-6) → (R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9)

Guidance literature:

methyl 3-oxotetradecanoate; With hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; ruthenium trichloride; In methanol; at 40 - 50 ℃; for 20h; under 3361.46 Torr;

With lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1016/j.tetlet.2006.01.137

Reference yield: 98.0%

methyl (R)-3-hydroxytetradecanoate (76062-97-0) → (R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃; for 2h;

Reference yield: 95.0%

(R)-1-cyanotridecan-2-ol (259799-90-1) → (R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9)

Guidance literature:

With hydrogenchloride; In dichloromethane; at 100 ℃; for 12h;

upstream raw materials:

3-hydroxytetradecanoic acid

Ethyl 3-hydroxytetradecanoate

vinyl acetate

3-oxomyristic acid

Downstream raw materials:

methyl (R)-3-hydroxytetradecanoate

(S)-methyl 3-hydroxymyristate

Benzyl-6-O-<6-O-acetyl-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosyl>-3,4-di-O-<α,α-D2>benzyl-2-desoxy-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosid

C₈₅H₁₁₆⁽²⁾H₆N₂O₂₄

Refernces

• 1、 Bai, Wen-Ju,Chen, Hao,Huang, Mengfei,Wang, Xiqing,Yan, Wenliang. "Enzymatic Regio- And Enantioselective C-H Oxyfunctionalization of Fatty Acids". . p. 10625 - 10630. Retrieved 2021/09/02.
• 2、 Tareq, Fakir Shahidullah,Shin, Hee Jae. "Bacilotetrins A and B, Anti-Staphylococcal Cyclic-Lipotetrapeptides from a Marine-Derived Bacillus subtilis". . p. 2889 - 2892. Retrieved 2017/12/01.