(S)-Methyl 3-hydroxytetradecanoate

Base Information

• Chemical Name: (S)-Methyl 3-hydroxytetradecanoate
• CAS No.: 76835-67-1
• Molecular Formula: C15H30 O3
• Molecular Weight: 258.401
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID10452253
• Nikkaji Number: J1.180.095E
• Wikidata: Q82272759
• Mol file: 76835-67-1.mol

Synonyms:76835-67-1;(S)-Methyl 3-hydroxytetradecanoate;Methyl (S)-3-Hydroxytetradecanoate;(S)-3-Hydroxy Myristic Acid Methyl Ester;METHYL (3S)-3-HYDROXYTETRADECANOATE;S-(3)-Hydroxymyristic Acid, Methyl Ester;(S)-Methyl3-hydroxytetradecanoate;METHYL-(S)-3-HYDROXYTETRADECANOATE;(3S)-3-Hydroxytetradeconoic Acid Methyl Ester;SCHEMBL8463481;DTXSID10452253;UOZZAMWODZQSOA-AWEZNQCLSA-N;AKOS016012185;HY-W127584;BP-29868;(R)-METHYL-3-HYDROXYTETRADECANOATE;CS-0185805;(S)-3-Hydroxytetradecanoic acid methyl ester

Chemical Property of (S)-Methyl 3-hydroxytetradecanoate

Chemical Property:

• Melting Point: 43-45°C
• Boiling Point: 359.1±15.0 °C(Predicted)
• PKA: 13.91±0.20(Predicted)
• PSA: 46.53000
• Density: 0.931±0.06 g/cm3(Predicted)
• LogP: 3.83130
• Storage Temp.: -20?C Freezer
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 258.21949481
• Heavy Atom Count: 18
• Complexity: 192

Purity/Quality:

99% ^*data from raw suppliers

(S)-3-HydroxyMyristicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(CC(=O)OC)O
• Isomeric SMILES: CCCCCCCCCCC[C@@H](CC(=O)OC)O
• Uses: (S)-3-Hydroxy Myristic Acid Methyl Ester is used in the syntheses of glucose-containing lipid A analogs with LPS-antagonistic activities.

Technology Process of (S)-Methyl 3-hydroxytetradecanoate

There total 23 articles about (S)-Methyl 3-hydroxytetradecanoate 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: 91.0%

methyl 3-oxotetradecanoate (22348-97-6) → (S)-methyl 3-hydroxymyristate (76835-67-1)

Guidance literature:

With hydrogenchloride; (R)-bis(acetato)(2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl)ruthenium; hydrogen; In ethanol; for 68h; under 76005.1 Torr; Inert atmosphere;

DOI:10.1016/j.tetasy.2008.11.012

Reference yield: 87.0%

methyl 3-oxotetradecanoate (22348-97-6) → methyl (R)-3-hydroxytetradecanoate (76062-97-0) + (S)-methyl 3-hydroxymyristate (76835-67-1)

Guidance literature:

methyl 3-oxotetradecanoate; With hydrogen; (S)-RuBINAP; In hydrogenchloride; methanol; under 1034.3 Torr;

for 15h; under 2585.74 Torr; Title compound not separated from byproducts; Heating;

DOI:10.1021/jo0162437

Reference yield:

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9) + (S)-methyl 3-hydroxymyristate (76835-67-1)

Guidance literature:

With Porcine Pancreas Lipase; water; In aq. phosphate buffer; at 36 ℃; for 7h; pH=7.6; enantioselective reaction;

DOI:10.1007/s00706-012-0917-z

upstream raw materials:

diazomethane

3-hydroxytetradecanoic acid

(3S)-3-hydroxytetradecanoic acid

methanol

Downstream raw materials:

methyl (S)-3-benzyloxytetradecanoate

(3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one

benzyl (S)-3-O-triethylsilyl-hydroxymyristate

(3S)-3-hydroxytetradecanoic acid

Refernces

• 1、 Wakimoto, Takayuki,Nakagishi, Shiori,Matsukawa, Nao,Tani, Shuji,Kai, Kenji. "A Unique Combination of Two Different Quorum Sensing Systems in the β-Rhizobium Cupriavidus taiwanensis". supporting information. p. 1876 - 1884. Retrieved 2020/07/06.
• 2、 Kuecuek, Hatice Baspinar,Yusufoglu, Ayse. "Enantioselective synthesis of 3-hydroxytetradecanoic acid and its methyl ester enantiomers as new antioxidants and enzyme inhibitors". . p. 1087 - 1091. Retrieved 2013/07/26.