Methyl 12-hydroxyoctadecanoate

Base Information

• Chemical Name: Methyl 12-hydroxyoctadecanoate
• CAS No.: 141-23-1
• Deprecated CAS: 82008-61-5,1037310-42-1,1037310-42-1
• Molecular Formula: C₁₉H₃₈O₃
• Molecular Weight: 314.509
• Hs Code.: 2918195000
• European Community (EC) Number: 205-471-8
• NSC Number: 2392
• UNII: P7UC7KGL82
• DSSTox Substance ID: DTXSID8027086
• Nikkaji Number: J141.036I
• Wikidata: Q27286334
• Metabolomics Workbench ID: 126916
• ChEMBL ID: CHEMBL2139695
• Mol file: 141-23-1.mol

Synonyms:methyl-12-hydroxystearate

Chemical Property of Methyl 12-hydroxyoctadecanoate

Chemical Property:

• Vapor Pressure: 4.63E-08mmHg at 25°C
• Melting Point: 48ºC
• Refractive Index: 1.455
• Boiling Point: 400 °C at 760 mmHg
• PKA: 15.40±0.20(Predicted)
• Flash Point: 147.6 °C
• PSA: 46.53000
• Density: 0.915 g/cm³
• LogP: 5.39170
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 89.94μg/L at 25℃
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 17
• Exact Mass: 314.28209507
• Heavy Atom Count: 22
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

Methyl 12-hydroxystearate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Stearates
• Canonical SMILES: CCCCCCC(CCCCCCCCCCC(=O)OC)O
• Description: Methyl 12-hydroxy stearate is won by direct esterfication of 12-Hydroxy stearic acid with methanol. Methyl 12-hydroxy stearate is sold in solid and liquid form. It is used in the continuous grease process. Greases made with Methyl 12-hydroxy stearate can be formulated to higher drop points. Greases experience less bleeding and improved oxidative stability. Methyl 12-hydroxy stearate is also used in textile ancillary, cosmetics and paper industry. appearance white to solid flakes or liquid melting point °C 45 - 53 AOCS Cc 1-25 colour (on 1” Lovibond) max. 3 yellow / max. 1,5 red AOCS 13e-92 acid value mg KOH/g max. 10 AOCS Cd 3d-63 iodine value 9 I2 /100g max. 5 AOCS Cd 1-25 hydroxyl value 160 - 178 AOCS Cd 13-60 saponification value mg KOH/g 170 - 180 AOCS Cd 3-25 water wt % max. 0,5 IS 548 unsaponifiable wt % max. 0,5 IS 548 titre of fatty acids °C 73 - 75 IS 548 Nickel + Iron ppm max. 10 ICP Sodium + Potassium ppm max. 20 ICP Magnesium + Calcium ppm max. 50 ICP
• Uses: Adhesives, inks, cosmetics greases. Methyl 12-Hydroxystearate is a fatty acid reagent used in the study of sphingomyelin through site specific deuterium labelling. Also used in the preparation of ricinoleate-based lipoconjugates of phenolic acids for antioxidant and antifubgal properties.

Technology Process of Methyl 12-hydroxyoctadecanoate

There total 40 articles about Methyl 12-hydroxyoctadecanoate 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: 99.0%

methanol (67-56-1) + 12-Hydroxystearic acid (106-14-9,78642-86-1,8039-23-4,27924-99-8,860114-96-1) → methyl 12-hydroxyoctadecanoate (6114-39-2,7309-59-3,82008-61-5,141-23-1)

Guidance literature:

With hydroxy-substituted sulfonic acid-functionalized silica (HO-SAS); In tetrahydrofuran; at 110 ℃; Flow reactor;

DOI:10.1246/bcsj.20170025

Reference yield: 85.0%

methyl 12-oxooctadecanoate (2380-27-0) → methyl 12-hydroxyoctadecanoate (6114-39-2,7309-59-3,82008-61-5,141-23-1)

Guidance literature:

With methanol; sodium tetrahydroborate; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2021.116254

Reference yield: 13.0%

methyl 12-hydroxyoctadec-trans-10-enoate (95080-12-9) → methyl 12-hydroxyoctadecanoate (6114-39-2,7309-59-3,82008-61-5,141-23-1) + Methyl stearate (112-61-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

upstream raw materials:

methyl ricinoleate

methyl 12-oxooctadecanoate

methyl ricinoleate

n-heptan1ol

Downstream raw materials:

12-Hydroxystearic acid

undecanedioic acid

12-(4'-nitro-4-dimethylaminoazobenzene-3'-carboxyloxy)stearic acid

12-(4'-nitro-4-dimethylaminostilbene-3'-carbonyloxy)stearic acid

Refernces

• 1、 Nelson,Applewhite. "". . p. 542. Retrieved 1966.
• 2、 Gensler,Abrahams. "-". . p. 4593,4595. Retrieved 1958.
• 3、 MASRI,GOLDBLATT,DE EDS,KOHLER. "Relation of cathartic activity to structural modifications of ricinoleic acid of castor oil.". . p. 999 - 1002. Retrieved 1962.
• 4、 Guin, Joyram,Paul, Subhasis. "A General Approach to Intermolecular Olefin Hydroacylation through Light-Induced HAT Initiation: An Efficient Synthesis of Long-Chain Aliphatic Ketones and Functionalized Fatty Acids". supporting information. p. 4412 - 4419. Retrieved 2021/02/05.
• 5、 Furuta, Akihiro,Fukuyama, Takahide,Ryu, Ilhyong. "Efficient flow fischer esterification of carboxylic acids with alcohols using sulfonic acid-functionalized silica as supported catalyst". . p. 607 - 612. Retrieved 2017/06/19.