Methyl 3-hydroxyhexadecanoate

Base Information

• Chemical Name: Methyl 3-hydroxyhexadecanoate
• CAS No.: 51883-36-4
• Molecular Formula: C17H34 O3
• Molecular Weight: 286.455
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID20966210
• Nikkaji Number: J109.455F
• Wikidata: Q27110093
• Metabolomics Workbench ID: 75574
• ChEMBL ID: CHEMBL2269935
• Mol file: 51883-36-4.mol

Synonyms:Methyl 3-hydroxyhexadecanoate;51883-36-4;3-HYDROXYHEXADECANOIC ACID METHYL ESTER;methyl 3-hydroxypalmitate;Hexadecanoic acid, 3-hydroxy-, methyl ester;3-hydroxypalmitic acid methyl ester;3-Hydroxy-palmitic acid methyl ester;CHEBI:29479;SCHEMBL1901941;Methyl 3-hydroxyhexadecanoate #;3-Hydroxy C16:0 methyl ester;CHEMBL2269935;DTXSID20966210;LMFA01050427;AKOS027321158;BP-29856;HY-132237;METHYL D(-)-3-HYDROXYHEXADECANOATE;CS-0181597;E80517;A929894;Q27110093;Hexadecanoic acid,3-hydroxy-, methyl ester;3-Hydroxyhexadecanoic Acid Methyl Ester

Chemical Property of Methyl 3-hydroxyhexadecanoate

Chemical Property:

• Vapor Pressure: 1.17E-07mmHg at 25°C
• Melting Point: 48-49 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 388.9°Cat760mmHg
• PKA: 13.91±0.20(Predicted)
• Flash Point: 147.4°C
• PSA: 46.53000
• Density: 0.922g/cm³
• LogP: 4.61150
• Storage Temp.: 2-8°C
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 286.25079494
• Heavy Atom Count: 20
• Complexity: 216

Purity/Quality:

NLT 98% ^*data from raw suppliers

3-HydroxyhexadecanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC(CC(=O)OC)O
• Description: 3-hydroxy Palmitic acid methyl ester (3-hydroxy PAME) is an esterized long-chain fatty acid involved in quorum sensing in R. solanacearum, a bacteria that causes lethal wilting in plants. 3-hydroxy-PAME (175 nM) increases levels of PhcA-regulated virulence factors, greater than 20-, 30-, and 25-fold for EPS I, EGL, and PME, respectively, in the AW1-83 strain of R. solanacearum. [Matreya, LLC. Catalog No. 1740]

Technology Process of Methyl 3-hydroxyhexadecanoate

There total 22 articles about Methyl 3-hydroxyhexadecanoate 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-oxohexadecanoate (14427-53-3) → (R)-β-hydroxyhexadecanoic acid methyl ester (51883-36-4,76898-45-8,127593-22-0,20404-35-7)

Guidance literature:

With hydrogen; [(R)-BINAP]RuBr₂; In methanol; at 50 ℃; for 24h; under 760.051 Torr;

DOI:10.1002/adsc.200390021

Reference yield: 97.0%

β-hydroxyhexadecanoic acid methyl ester (51883-36-4) + trimethyl orthoformate (149-73-5) → (R)-β-hydroxyhexadecanoic acid methyl ester (51883-36-4,76898-45-8,127593-22-0,20404-35-7)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 0.75h; Heating;

DOI:10.1016/0957-4166(96)00426-0

Reference yield: 10.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (R)-β-hydroxypalmitic acid (928-17-6,2398-34-7,83780-74-9,20595-04-4) → pentadecan-2-one (2345-28-0) + (R)-β-hydroxyhexadecanoic acid methyl ester (51883-36-4,76898-45-8,127593-22-0,20404-35-7)

Guidance literature:

In diethyl ether; Yield given;

DOI:10.1021/jo00299a041

upstream raw materials:

methyl 3-oxohexadecanoate

methanol

β-hydroxypalmitic acid

diazomethane

Downstream raw materials:

(R)-β-hydroxypalmitic acid

(R)-β-hydroxyhexadecanoic acid methyl ester

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[(R)-1-(benzotriazol-1-yloxycarbonylmethyl)-tetradecyl] ester 5-tert-butyl ester

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-[(R)-1-(2,2,2-trichloro-ethoxycarbonylmethyl)-tetradecyl] ester

Refernces

• 1、 Hollaus, Ralph,Ittig, Simon,Hofinger, Andreas,Haegman, Mira,Beyaert, Rudi,Kosma, Paul,Zamyatina, Alla. "Chemical synthesis of burkholderia lipid a modified with glycosyl phosphodiester-linked 4-amino-4-deoxy-β-L-arabinose and its immunomodulatory potential". supporting information. p. 4102 - 4114. Retrieved 2015/10/19.
• 2、 Hasdemir, Belma,Onar, Huelya Elik,Yusufolu, Aye. "Asymmetric synthesis of long chain β-hydroxy fatty acid methyl esters as new elastase inhibitors". . p. 1100 - 1105. Retrieved 2012/11/07.