Methyl palmitate

Base Information

• Chemical Name: Methyl palmitate
• CAS No.: 112-39-0
• Molecular Formula: C17H34O2
• Molecular Weight: 270.456
• Hs Code.: 29157090
• European Community (EC) Number: 203-966-3
• NSC Number: 4197
• UNII: DPY8VCM98I
• DSSTox Substance ID: DTXSID4029149
• Nikkaji Number: J1.994A
• Wikidata: Q16676086
• Metabolomics Workbench ID: 4115
• ChEMBL ID: CHEMBL335125
• Mol file: 112-39-0.mol

Synonyms:methyl palmitate;palmitic acid methyl ester

Chemical Property of Methyl palmitate

Chemical Property:

• Appearance/Colour: Clear colorless liquid or low melting solid
• Vapor Pressure: 0.000149mmHg at 25°C
• Melting Point: 32-35 °C(lit.)
• Refractive Index: n20/D 1.4512(lit.)
• Boiling Point: 332.1 °C at 760 mmHg
• Flash Point: 152.8 °C
• PSA: 26.30000
• Density: 0.865 g/cm³
• LogP: 5.64070
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility.: INSOLUBLE
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 270.255880323
• Heavy Atom Count: 19
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

Methyl Palmitate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC
• Description: Saturated fatty acids are synthesized by both plants and animals from acetyl coenzyme A as a form of long-term energy storage. Palmitic acid is a common 16-carbon saturated fat that represents 10-20% of the normal human dietary fat intake, and approximately 25% of the total plasma fatty acids in plasma lipoproteins. Saturated free fatty acids induce the expression of cyclooxygenase-2. Palmitic acid methyl ester (MP) is a fatty acid ester whose concentration in cells is modulated by methanol. In studies with isolated Kupffer cells, MP inhibits phagocytosis and decreases cell viability. In cells treated with lipopolysaccharide, it also decreases secretion of interleukin-10, TNF-α, nitric oxide, and prostaglandin E2. This effect is thought to occur by the inhibition of NF-κB.
• Uses: Methyl Palmitate is a fatty acid ester essential oil that naturally occurs in many plant species. Methyl Palmitate concentration in cells are known to be modulated by methanol. In experimental studies with isolated Kupffer cells, Methyl palmitate exhibited inhibitory activity towards phagocytosis and decreases cell viability. Methyl palmitate can be used as an additive in food and cosmetic industries for the stabilization of fats and oil products by slowing down the auto-oxidation of unsaturated fatty acids. Methyl palmitate is used in the preparation of detergents, emulsifiers, wetting agents, stabilizers, resins, lubricants, plasticizers and animal feeds. It exhibits an anti-inflammatory and anti-fibrotic agent and prevents bleomycin-induced lung inflammation and fibrosis in rats. In addition, it also prevents carbon tetrachloride-induced liver fibrosis linked to reduce transforming growth factor beta, which is a secreted protein that controls proliferation, cellular differentiation and other functions in most cells.

Technology Process of Methyl palmitate

There total 138 articles about Methyl palmitate 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: 99.9%

methanol (67-56-1) + glyceroltripalmitate (555-44-2) → hexadecanoic acid methyl ester (112-39-0) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0)

Guidance literature:

With [quaternary CH₃I ammonizated co(divinylbenzene-N-vinylimidazolate)polymer][SO₃CF₃]; at 65 ℃; for 16h;

DOI:10.1021/ja307455w

Reference yield:

methanol (67-56-1) + 4-nitrophenyl palmitate (1492-30-4) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + hexadecanoic acid methyl ester (112-39-0)

Guidance literature:

With Thermomyces lanuginosus lipase; for 7h; Enzymatic reaction;

DOI:10.1002/cctc.202101050

Reference yield:

sitoindoside I (18749-71-8) → hexadecanoic acid methyl ester (112-39-0) + 1-hexadecylcarboxylic acid (57-10-3)

Guidance literature:

With sodium methylate; In methanol; for 3h; Title compound not separated from byproducts; Ambient temperature;

upstream raw materials:

methanol

toluene-4-sulfonic acid

1-hexadecylcarboxylic acid

formaldehyd

Downstream raw materials:

2-methylheptadecan-2-ol

eicosane-4,5-dione

2-O-benzyl-1,3-di-O-palmitoyl-rac-glycerol

7-Hexyl-docosan

Refernces

• 1、 Long, Jia-Tang,Fan, Hong-Xia,Zhou, Zheng-Qun,Sun, Wan-Yang,Li, Qing-Wen,Wang, Ying,Ma, Min,Gao, Hao,Zhi, Hui. "The major zeaxanthin dipalmitate derivatives from wolfberry". . p. 746 - 753. Retrieved 2020.
• 2、 Chang, Binbin,Tian, Yanlong,Shi, Weiwei,Liu, Jiyang,Xi, Fengna,Dong, Xiaoping. "Magnetically separable porous carbon nanospheres as solid acid catalysts". . p. 20999 - 21006. Retrieved 2013.
• 3、 Kastner, James R.,Miller, Joby,Geller, Daniel P.,Locklin, Jason,Keith, Lawrence H.,Johnson, Tyson. "Catalytic esterification of fatty acids using solid acid catalysts generated from biochar and activated carbon". . p. 122 - 132. Retrieved 2012.
• 4、 Shah, Mayank D.,Kharkar, Prashant S.,Sahu, Niteshkumar U.,Peerzada, Zoya,Desai, Krutika B.. "Potassium 2-methoxy-4-vinylphenolate: A novel hit exhibiting quorum-sensing inhibition in: Pseudomonas aeruginosa via LasIR/RhlIR circuitry". . p. 40228 - 40239. Retrieved 2019.
• 5、 Wu, Qin,Liu, Fujian,Yi, Xianfeng,Zou, Yongcun,Jiang, Lilong. "A solvent-free, one-step synthesis of sulfonic acid group-functionalized mesoporous organosilica with ultra-high acid concentrations and excellent catalytic activities". . p. 1020 - 1030. Retrieved 2018.
• 6、 Pirez, Cyril,Lee, Adam F.,Jones, Christopher,Wilson, Karen. "Can surface energy measurements predict the impact of catalyst hydrophobicity upon fatty acid esterification over sulfonic acid functionalised periodic mesoporous organosilicas?". . p. 167 - 173. Retrieved 2014.
• 7、 Wang, Xia,Meng, QianQian,Peng, XingRong,Hu, GuiLin,Qiu, MingHua. "Identification of new diterpene esters from green Arabica coffee beans, and their platelet aggregation accelerating activities". . p. 251 - 257. Retrieved 2018.
• 8、 Gonzales, Antonio G.,Barrera, Jaime Bermejo,Marante, Francisco J. Toledo. "THE STEROIDS AND FATTY ACIDS OF THE BASIDIOMYCETE SCLERODERMA POLYRHIZUM". . p. 1049 - 1050. Retrieved 1983.
• 9、 Dean, Francis M.,Khan, Hafizzullah,Minhaj, Najme,Prakash, Satya,Zaman, Asif. "The Structure of Wightianone, the Pigment of a Clathrate from Calophyllum wightianum". . p. 1755 - 1759. Retrieved 1984.
• 10、 Poonjarernsilp, Chantamanee,Sano, Noriaki,Sawangpanich, Nut,Charinpanitkul, Tawatchai,Tamon, Hajime. "Effect of Fe/Fe2O3 loading on the catalytic activity of sulfonated single-walled carbon nanohorns for the esterification of palmitic acid". . p. 4936 - 4943. Retrieved 2014.