2420-35-1

Basic information

• Product Name: METHYL 2-HYDROXYOCTADECANOATE
• Synonyms: DL-ALPHA-HYDROXYSTEARIC ACID METHYL ESTER;METHYL 2-HYDROXYOCTADECANOATE;2-HYDROXY C18:0 METHYL ESTER;dl-A-hydroxystearic acid methyl ester;dl-α-hydroxystearic acid methyl ester;methyl (±)-2-hydroxystearate;DL-α-Hydroxystearic acid methyl ester, Methyl 2-hydroxyoctadecanoate;2-Hydroxyoctadecanoic acid methyl ester
• CAS NO: 2420-35-1
• Molecular Formula: C₁₉H₃₈O₃
• Molecular Weight: 314.5
• Mol File: 2420-35-1.mol

Chemical Properties

• Melting Point: 64-66 °C
• Boiling Point: 354.8±10.0 °C(Predicted)
• Appearance: /
• Density: 0.915±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 13.03±0.20(Predicted)
• CAS DataBase Reference: METHYL 2-HYDROXYOCTADECANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-HYDROXYOCTADECANOATE(2420-35-1)
• EPA Substance Registry System: METHYL 2-HYDROXYOCTADECANOATE(2420-35-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2420-35-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2-HYDROXYOCTADECANOATE is used as a key component in the synthesis of lipid-nucleotide conjugate anti-HIV agents. Its application is primarily due to its ability to increase phosphodiester bond cleavage, which in turn enhances the amount of liberated intracellular nucleotides, contributing to the effectiveness of these anti-HIV agents.
Used in Lipid Membrane Research:
In the field of biochemistry and membrane research, METHYL 2-HYDROXYOCTADECANOATE is utilized for its capacity to broaden phase transitions in lipid membranes. This property makes it a valuable tool for studying the behavior and characteristics of lipid membranes, which are crucial components of cell structures and have implications in various biological processes and diseases.

Upstream product

• 67-56-1 methanol 
• 1234851-89-8 C₃₉H₇₇NO₁₀ 
• 1234851-90-1 C₄₀H₇₉NO₁₀ 
• 1588950-14-4 (2S,3S,4R)-2-{[(2R)-2-hydroxyoctdecanoy]amino}hexaeicosane-1,3,4-triol 
• 57-11-4 stearic acid 
• 83517-82-2 Methyl 2-methoxyoctadecanoate 
• 142-94-9 2-bromostearic acid 
• 3196-18-7 Methyl 2-bromostearate 
• 629-22-1 2-hydroxystearic acid 
• 186581-53-3 diazomethane 

Downstream Products

• 120977-29-9 C₂₆H₃₇F₅O₄ 
• 506-12-7 heptadecanoic acid 
• 629-22-1 2-hydroxystearic acid 

Relevant articles and documents

Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents

A series of α- and β-carboxylated phospholipid prodrugs of dideoxy nucleosides have been synthesized and evaluated against HIV. An increase in biological effect with a factor of 500 has only been observed for the adenine nucleoside, which suggests that this prodrug approach is base specific.

New lipoxygenase inhibitory sphingolipids from Chrozophora plicata

Two new sphingolipids plicatin A [(2S,3S,4R)-2-{[(2R)-2-hydroxyoctdecanoyl] amino}hexaeicosane-1,3,4-triol (1)] and plicatin B [(2S,3S,4R,10E)-2-{[(2R)-2- hydroxyoctdecanoyl]amino}tricont-10-ene-1,3,4-triol (2)], together with 4-hydroxybenzaldehyde, scopoletin, uracil, and dl-threonolactone were isolated from the methanolic extract of the whole plant of Chrozophora plicata. The structures of these compounds were established using 1D (1H, 13C) and 2D NMR (HMQC, HMBC, and COSY) spectroscopy and mass spectrometry (EI-MS and HR-EI-MS) and in comparison with the reported data in the literature. Compounds 1 and 2 showed inhibitory potential against enzyme lipoxygenase with IC50 values 195.1 and 102.3 μM, respectively.

Structural determination of cerebrosides isolated from Asterias amurensis starfish eggs using high-energy collision-induced dissociation of sodium-adducted molecules

Six cerebrosides were isolated from the eggs of the starfish Asterias amurensis using solvent extraction, silica gel column chromatography, and reversed-phase high-performance liquid chromatography. This study demonstrated that the structures of cerebrosides could be completely characterized, based on their sodium-adducted molecules, using fast atom bombardment (FAB) tandem mass spectrometry. The high-energy collision-induced dissociation of the sodium-adducted molecule, [M+Na]+, of each cerebroside molecular species generated abundant ions, providing information on the compositions of the 2-hydroxy fatty acids and long-chain sphingoid bases, as well as the sugar moiety polar head group. Each homologous ion series along the fatty acid and aliphatic chain of the sphingoid base was useful for locating the double-bond positions of both chains and the methyl branching position of the long-chain base. The N-fatty acyl portions were primarily long-chain saturated or monoenoic acids (C16 to C24) with an α-hydroxy group. The sphingoid long-chain base portions were aliphatic chains (C18 or C22) with two or three degrees of unsaturation and with or without methyl branching.

Structural determination of glucosylceramides isolated from marine sponge by fast atom bombardment collision-induced dissociation linked scan at constant B/E

Five glucosylceramides (GlcCers) were isolated by reversed phase high-performance liquid chromatography from the MeOH extracts of amarine sponge, Haliclona (Reniera) sp., collected from the coast of Ulleung Island, Korea, and analyzed by fast atom bombard

Gas chromatography/electron-capture negative ion mass spectrometry for the quantitative determination of 2- and 3-hydroxy fatty acids in bovine milk fat

2- and 3-hydroxy fatty acids (2- and 3-OH-FAs) are bioactive substances reported in sphingolipids and bacteria. Little is known of their occurrence in food. For this reason, a method suitable for the determination of OH-FAs at trace levels in bovine milk fat was developed. OH-FAs (and conventional fatty acids in samples) were converted into methyl esters and the hydroxyl group was derivatized with pentafluorobenzoyl (PFBO) chloride to give PFBO-O-FA methyl esters. These derivatives with strong electron affinity were determined by gas chromatography interfaced to mass spectrometry using electron-capture negative ion in the selected ion monitoring mode (GC/ECNI-MS-SIM). This method proved to be highly sensitive and selective for PFBO-O-FA methyl esters. For the analysis of samples, two internal standards were used. For this purpose, 9,10-dideutero-2-OH-18:0 methyl ester (ISTD-1) from 2-OH-18:1(9c) methyl ester as well as the ethyl ester of 3-PFBO-O-12:0 (ISTD-2) was synthesized. ISTD-1 served as a recovery standard whereas ISTD-2 was used for GC/MS measurements. The whole-sample cleanup consisted of accelerated solvent extraction of dry bovine milk, addition of ISTD 1, saponification, conversion of fatty acids into methyl esters by use of boron trifluoride, separation of the methyl esters of OH-FAs from nonsubstituted FAs on activated silica, conversion of OH-FAs methyl esters into PFBO-O-FA methyl esters, addition of ISTD-2, and measurement by GC/ECNI-MS-SIM. By this method, ten OH-FAs were quantified in bovine milk fat with high precision in the range from 0.02 ± 0.00 to 4.49 ± 0.29 mg/100 g of milk fat.

Short Syntheses of Furan and Catechol Derivatives. A Synthesis of Hydrourushiol

The copper-catalyzed decomposition of ethyl diazopyruvate in enol ethers is shown to yield alkoxydihydrofuroates, whose exposure to acid leads to ethyl α-furoates.The latter are also the products of the copper-induced interaction of ethyl diazopyruvate with acetylenes.The conversion of one furoate into a furan and another into a furanoid terpene system is described.The Fetizon oxidation of primary β-alkoxycyclopropylcarbinols is shown to give alkoxydihydrofurans.The formation of a masked, 1,2,5-triketo system by the copper-assisted decomposition of 1-diazo-3,3-dimethoxy-2-butanone in n-butyl vinyl ether and subsequent acid-catalyzed unraveling of the resultant β-alkoxycyclopropyl ketone are portrayed.Ring scission of the intermediate in methanolic acid at elevated temperature yields veratrole.Utilization of this method of synthesis of aromatic compounds of the catehol type in the synthesis of hydrourushiol is illustrated.