Methyl (3R)-3-hydroxyoctanoate

Base Information

• Chemical Name: Methyl (3R)-3-hydroxyoctanoate
• CAS No.: 78672-90-9
• Molecular Formula: C9H18O3
• Molecular Weight: 174.24
• UNII: 2EAE8PD8QC
• DSSTox Substance ID: DTXSID80502214
• Nikkaji Number: J67.200I
• Wikidata: Q82355063
• Mol file: 78672-90-9.mol

Synonyms:78672-90-9;methyl (R)-3-hydroxyoctanoate;Methyl (3R)-3-hydroxyoctanoate;2EAE8PD8QC;Octanoic acid, 3-hydroxy-, methyl ester, (3R)-;methyl (3r)-hydroxyoctanoate;Methyl 3-hydroxyoctanoate, (R)-;UNII-2EAE8PD8QC;R-3-hydroxyoctanoic acid methyl ester;Octanoic acid, 3-hydroxy-, methyl ester, (-)-;Octanoic acid, 3-hydroxy-, methyl ester, (R)-;DTXSID80502214;FHWBTAQRRDZDIY-MRVPVSSYSA-N;(r)-3-hydroxyoctanoate methyl ester

Chemical Property of Methyl (3R)-3-hydroxyoctanoate

Chemical Property:

• Boiling Point: 259.9±13.0 °C(Predicted)
• PKA: 14.09±0.20(Predicted)
• PSA: 46.53000
• Density: 0.976±0.06 g/cm3(Predicted)
• LogP: 1.49070
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 174.125594432
• Heavy Atom Count: 12
• Complexity: 123

Purity/Quality:

95+% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(CC(=O)OC)O
• Isomeric SMILES: CCCCC[C@H](CC(=O)OC)O

Technology Process of Methyl (3R)-3-hydroxyoctanoate

There total 18 articles about Methyl (3R)-3-hydroxyoctanoate 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: 96.0%

methyl 3-oxooctanoate (22348-95-4) → methyl (R)-(-)-3-hydroxydecanoate (78672-90-9,85549-54-8)

Guidance literature:

With hydrogen; [Ru(R)-SYNPHOSBr₂]; at 50 ℃; for 0.5h; under 7500.6 Torr;

DOI:10.1016/j.tetasy.2006.11.048

Reference yield: 95.0%

Ru2 Cl4 ((+)-(T)BINAP)2 Et3 N + methyl 3-oxooctanoate (22348-95-4) → methyl (R)-(-)-3-hydroxydecanoate (78672-90-9,85549-54-8)

Guidance literature:

In methanol; dichloromethane; nitrogen;

Reference yield: 92.0%

(E)-methyl 3-oxo-6-octenoate (62344-14-3) → methyl (R)-(-)-3-hydroxydecanoate (78672-90-9,85549-54-8)

Guidance literature:

With hydrogen; <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3; In methanol; for 48h; under 76000 Torr; Ambient temperature;

DOI:10.1021/ja00226a041

upstream raw materials:

diazomethane

(R)-3-hydroxy-octanoic acid

vinyl acetate

3-hydroxyoctanoic acid methyl ester

Downstream raw materials:

(R)-3-hydroxy-octanoic acid

(S)-3-hydroxyoctanoic acid benzyl ester

(R)-massoialactone

(R)-3-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-octanoic acid methyl ester

Refernces

• 1、 Chen, Haotong,Olson, Andrew S.,Su, Wei,Dussault, Patrick H.,Du, Liangcheng. "Fatty acyl incorporation in the biosynthesis of WAP-8294A, a group of potent anti-MRSA cyclic lipodepsipeptides". . p. 105753 - 105759. Retrieved 2015/12/26.
• 2、 Touati, Ridha,Ratovelomanana-Vidal, Virginie,Hassine, Bechir Ben,Genet, Jean-Pierre. "Synthesis of enantiopure (R)-(-)-massoialactone through ruthenium-SYNPHOS asymmetric hydrogenation". . p. 3400 - 3405. Retrieved 2007/10/03.