Methyl 3-hydroxyoctanoate

Base Information

• Chemical Name: Methyl 3-hydroxyoctanoate
• CAS No.: 7367-87-5
• Molecular Formula: C9H18O3
• Molecular Weight: 174.24
• European Community (EC) Number: 230-917-3
• UNII: UQU7C4XEV7
• DSSTox Substance ID: DTXSID70276098
• Nikkaji Number: J140.295A
• Mol file: 7367-87-5.mol

Synonyms:Methyl 3-hydroxyoctanoate;7367-87-5;85549-54-8;3-hydroxyoctanoic acid methyl ester;UQU7C4XEV7;Octanoic acid, 3-hydroxy-, methyl ester;EINECS 230-917-3;3-Hydroxy octanoic acid methyl ester;DL-B-HYDROXYCAPRYLIC ACID METHYL ESTER;Methyl3-hydroxyoctanoate;UNII-UQU7C4XEV7;Methyl 3-hydroxyoctanoate #;3-Hydroxy C8:0 methyl ester;SCHEMBL1427581;METHYL 3-HYDROXYCAPRYLATE;DTXSID70276098;3-hydroxycaprylic acid methyl ester;AKOS006271868;SB85093;SS-4994;Octanoic acid,3-hydroxy-, methyl ester;E89406;.BETA.-HYDROXYOCTANOIC ACID METHYL ESTER

Chemical Property of Methyl 3-hydroxyoctanoate

Chemical Property:

• Vapor Pressure: 0.00184mmHg at 25°C
• Refractive Index: 1.439
• Boiling Point: 259.9 °C at 760 mmHg
• PKA: 14.09±0.20(Predicted)
• Flash Point: 102.2 °C
• PSA: 46.53000
• Density: 0.976 g/cm³
• 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:

99% ^*data from raw suppliers

3-HydroxyoctanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(CC(=O)OC)O
• Uses: 3-Hydroxyoctanoic Acid Methyl Ester is a volatile ester found in fruit juices used as a flavoring compound.

Technology Process of Methyl 3-hydroxyoctanoate

There total 28 articles about Methyl 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: 88.0%

(2R*,3R*)-methyl 2-bromo-3-hydroxyoctanoate (132377-77-6) → 3-hydroxyoctanoic acid methyl ester (7367-87-5,85549-54-8)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In ethanol; for 2h; under 760 Torr;

DOI:10.1021/jo00008a051

Reference yield: 85.0%

hexanal (66-25-1) + bromoacetic acid methyl ester (96-32-2) → 3-hydroxyoctanoic acid methyl ester (7367-87-5,85549-54-8)

Guidance literature:

With zinc; In tetrahydrofuran; at 66 ℃; for 0.0166667h;

DOI:10.1055/s-0034-1379479

Reference yield:

polyhydroxyalkanoate → C14H20O4 + 3-hydroxybutyric acid methyl ester (1487-49-6) + 3-hydroxyoctanoic acid methyl ester (7367-87-5,85549-54-8) + methyl 3-hydroxydecanoate (62675-82-5) + β-hydroxydodecanoic acid methyl ester (72864-23-4,85464-97-7) + (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) + 3-hydroxy-5-phenyl-pentanoic acid methyl ester (129880-16-6)

Guidance literature:

Product distribution / selectivity;

upstream raw materials:

diazomethane

3-hydroxyoctanoic acid

carbon dioxide

1-Bromomercuri-2-heptanol

Downstream raw materials:

methyl 3-oxooctanoate

methyl (E)-oct-2-enoate

3-hydroxyoctanoic acid

(S)-methyl 3-hydroxyoctanoate

Refernces

• 1、 Ensari, Yunus,Dhoke, Gaurao V.,Davari, Mehdi D.,Bocola, Marco,Ruff, Anna Jo?lle,Schwaneberg, Ulrich. "Inversion of cpADH5 Enantiopreference and Altered Chain Length Specificity for Methyl 3-Hydroxyalkanoates". . p. 12636 - 12645. Retrieved 2017/09/18.
• 2、 Sailer, Miloslav,Dubicki, Krystyn I.,Sorensen, John L.. "The synthesis of medium-chain-length β-hydroxy esters via the reformatsky reaction". . p. 79 - 82. Retrieved 2015/02/02.