542-44-9

Basic information

• Product Name: MONOPALMITIN
• Synonyms: (±)-hexadecanoicacid2,3-dihydroxypropylester;1,2,3-Propanetriol 1-hexandecanoyl ester;1-Monopalmitoylglycerol;1-Palmitoylglycerol;2,3-Dihydroxypropyl palmitate;Glycerinfattyacidester;Glycerol 1-monopalmitate;Glycerol 1-palmitate
• CAS NO: 542-44-9
• Molecular Formula: C₁₉H₃₈O₄
• Molecular Weight: 330.50262
• EINECS: 208-812-9
• Product Categories: Ester Type (Surfactants);Functional Materials;Nonionic Surfactants;Surfactants;Fatty Acid Derivatives & Lipids;Glycerols;Glycerols, Fatty Acid Derivatives & Lipids
• Mol File: 542-44-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 75 °C
• Boiling Point: 451.3°Cat760mmHg
• Flash Point: 146.7°C
• Appearance: /
• Density: 0.969g/cm³
• Storage Temp.: −20°C
• Solubility: soluble in Methanol
• PKA: 13.16±0.20(Predicted)
• BRN: 1728235
• CAS DataBase Reference: MONOPALMITIN(CAS DataBase Reference)
• NIST Chemistry Reference: MONOPALMITIN(542-44-9)
• EPA Substance Registry System: MONOPALMITIN(542-44-9)

Safety Data

• WGK Germany: 1
• RTECS: MO1852000
• Hazardous Substances Data: 542-44-9(Hazardous Substances Data)

Usage

Description

1-Palmitoyl-rac-glycerol is a monoacylglycerol that contains palmitic acid at the sn-1 position. It is an emulsifying agent and has been used to increase the viscoelasticity of processed cheese.

Chemical Properties

White Solid

Biochem/physiol Actions

α-Monopalmitin is a glycerol esterified fatty acid, monoacylglycerol, found in lipid structures such as ceramides. 1-Palmitoylglycerol may be used as a substrate for the identification and differentiation of enzymes that hydrolyze or transfer monoacylglycerols such as neuropathy target esterase(s) and monoacylglycerol acyltransferase(s) (MAG).

InChI:InChI=1/C19H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-17-18(21)16-20/h18,20-21H,2-17H2,1H3

Upstream product

• 57416-03-2 (R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-hexadecanoate 
• 32899-40-4 2,2'-O-Methylen-bis-(1-O-palmitoyl-sn-glycerin) 
• 30563-15-6 1-O-trityl-3-O-palmitoyl-sn-glycerol 
• 1487-50-9 1-O-hexadecanoyl-3-O-benzyl-sn-glycerol 
• 112-67-4 n-hexadecanoyl chloride 
• 119617-61-7 (S)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-hexadecanoate 
• 57-10-3 1-hexadecylcarboxylic acid 
• 36653-82-4 1-Hexadecanol 
• 43211-62-7 allyl hexadecanoate 
• 143003-65-0 (2R)-3-(benzyloxy)-2-hydroxypropyl hexadecanoate 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 

Downstream Products

• 2190-30-9 1,2-dioleoyl-3-palmitoylglycerol 
• 33625-90-0 1,2-dipalmitoyl-3-triphenylmethyl-sn-glycerol 
• 1396745-74-6 (S)-2,3-di[(E)-2-methyl-2-butenoyloxy]propyl n-hexadecanoate 
• 1396772-04-5 (R)-2,3-di[(E)-2-methyl-2-butenoyloxy]propyl n-hexadecanoate 
• 1396745-86-0 C₃₉H₅₂F₆O₈ 
• 65390-75-2 sn-1,2-dioleoyl-3-palmitoylglycerol 
• 907216-71-1 3-hexadecanoyl-1,2-di(cis-hexadec-9-enoyl)-sn-glycerol 
• 134907-95-2 1-hexadecanoyl-2-[(9Z)-octadeca-9-enoyl]-3-tetradecanoyl-sn-glycerol 
• 30563-16-7 2,3-dipalmitoyl-1-triphenylmethyl-sn-glycerol 
• 2190-15-0 1-palmitin-2,3-dilinolein 
• 30563-15-6 1-O-trityl-3-O-palmitoyl-sn-glycerol 
• 13190-01-7 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine 

Relevant articles and documents

Synthesis of enantiopure ABC-type triacylglycerols

The synthesis of twelve enantiopure structured triacylglycerols (TAGs) of the ABC type possessing three different fatty acids is described by a six-step chemoenzymatic approach starting from (S)-solketal. Eight of the TAGs possess two different saturated fatty acyl groups located in the sn-1 and sn-2 positions with an unsaturated fatty acyl group in the remaining sn-3 position of the glycerol skeleton, whereas the remaining four possess two different saturated acyl groups in the terminal sn-1 and sn-3 positions with an unsaturated acyl group in the sn-2 position. The former group was synthesised by a six-step chemoenzymatic route involving a highly regioselective immobilised Candida antarctica lipase. The second group was prepared by a similar six-step approach, that required two separate lipase steps. Such enantiopure TAGs are strongly demanded as standards for enantiospecific analysis of intact TAGs in fats and oils.

Synthesis of enantiopure structured triacylglycerols

The synthesis of nine enantiopure structured triacylglycerols (TAGs) of the AAB type is described, all possessing the (S)-absolute configuration. Six of them possess one saturated and two identical unsaturated fatty acyl chains, whereas the remaining three possess two identical saturated fatty acids along with one unsaturated fatty acid. The former group was synthesized by a five-step chemoenzymatic route involving a highly regioselective immobilized Candida antarctica lipase, starting from enantiopure (R)-solketal. The second group was prepared by a fully chemical five-step approach based on the same chiral precursor. Such enantiopure TAGs are strongly required as standards for the enantiospecific analysis of intact TAGs in fats and oils.

Pheromone synthesis. Part 253: Synthesis of the racemates and enantiomers of triglycerides of male Drosophila fruit flies with special emphasis on the preparation of enantiomerically pure 1-monoglycerides

The racemates and enantiomers of triglycerides 1aee (2,3-ditigloyloxypropyl esters of palmitic, palmitoleic, stearic, oleic, and linoleic acids) of male Drosophila fruit flies were synthesized in three steps from the racemate and enantiomers of 2,3-acetoneglycerol (2) via 1-monoglycerides 4aee derived from the above fatty acids. Appropriate conditions were established for the preparation of enantiomerically pure 1-monoglycerides 4aee, and their enantiomeric purities were determined by NMR analysis of the corresponding bis-(R)-MTPA esters.