10550-58-0

Usage

Uses

Used in Pharmaceutical Industry:
3-O-HEXADECYL-SN-GLYCEROL is used as a key component in the synthesis of phosphatidylcholine analogs, which serve as phospholipase A2 inhibitors. These inhibitors play a crucial role in modulating the activity of phospholipase A2, an enzyme involved in the degradation of cell membranes and the production of inflammatory mediators. By inhibiting this enzyme, phosphatidylcholine analogs can help in the management of inflammation and related conditions.
Used in Cardiovascular Health:
3-O-HEXADECYL-SN-GLYCEROL is also utilized in the preparation of oxidized phospholipids, which have been shown to have potential benefits in the prevention and treatment of atherosclerosis and other cardiovascular disorders. Atherosclerosis is a condition characterized by the buildup of plaque in the arteries, which can lead to heart disease, stroke, and other complications. Oxidized phospholipids, derived from 3-O-HEXADECYL-SN-GLYCEROL, may help in reducing the formation of plaque and improving overall cardiovascular health.

InChI:InChI=1/C19H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-22-18-19(21)17-20/h19-21H,2-18H2,1H3/t19-/m1/s1

Upstream product

• 57959-37-2 3-O-hexadecyl-1,2-O-isopropylidene-sn-glycerol 
• 119879-84-4 3-O-hexadecyl-1-O-(tert-butyldiphenylsilyl)-sn-glycerol 
• 20779-14-0 methanesulfonic acid hexadecyl ester 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 36653-82-4 1-Hexadecanol 
• 57044-25-4 (R)-oxiranemethanol 
• 112-82-3 hexadecanyl bromide 
• 121403-67-6 hexacedanyl (S)-2-oxiranylmethyl ether 
• 107209-89-2 rac-1-brom-3-hexadecyloxy-propanol-2 
• 1187886-96-9 (2S)-3-(hexadecyloxy)-2-hydroxypropyl β-D-lyxofuranoside 
• 89496-73-1 4-(n-hexadecyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 174289-76-0 1-hexadecyl-2,3-dibenzylglycerol 

Downstream Products

• 96093-53-7 (S)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-ol 
• 90130-75-9 3-O-hexadecyl-2-lyso-sn-glycero-1-phosphocholine 
• 96998-53-7 3-O-hexadecyl-2-O-benzyl-sn-glycero-1-phosphocholine 
• 82535-83-9 (-)-1-O-hexadecyl-2-O-acetyl-sn-glycerol 
• 96022-71-8 2-O-Benzyl-3-O-hexadecyl-1-O-<2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl>-sn-glycerin 
• 112014-15-0 1-hexadecyl-2-thioacetyl-2-deoxyglycerol 
• 96801-55-7 1-O-hexadecyl-2-deoxy-2-thio-S-acetyl-sn-glyceryl-3-phosphorylcholine 
• 112014-14-9 1-Hexadecyl-2-(4-nitrobenzenesulfonyl)-D-glycerol 
• 121358-36-9 4-Nitro-benzenesulfonic acid (S)-1-hexadecyloxymethyl-2-trityloxy-ethyl ester 
• 122822-37-1 C₃₉H₅₄F₆O₇ 
• 120964-49-0 (-)-1-O-hexadecyl-2-O-methyl-sn-glycerol 
• 92471-46-0 (R)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-ol 
• 119944-30-8 3‐hexadecyloxy‐2R‐hydroxyl propyl‐1‐p‐toluene sulphonate 

Relevant academic research and scientific papers

Activation of n-3 polyunsaturated fatty acids as oxime esters: A novel approach for their exclusive incorporation into the primary alcoholic positions of the glycerol moiety by lipase

A novel approach has been developed for activating the highly bioactive long-chain n-3 polyunsaturated fatty acids EPA and DHA as oxime esters and incorporating them exclusively to the end-positions of glycerol and enantiopure 1-O-alkylglycerols. The Candida antarctica lipase B was observed to display a superb regioselectivity when using the acetoxime esters of EPA and DHA as acyldonors under mild condition to keep acyl-migration side-reaction under complete control. Regiopure 1,3-diacylglycerols, 1-O-alkyl-3-acyl-sn-glycerols and their antipodes possessing EPA and DHA were afforded in very high purity and yields.

Homologues and isomers of noladin ether, a putative novel endocannabinoid: Interaction with rat cannabinoid CB1 receptors

Two regioisomers and 13 analogues of the putative endocannabinoid noladin ether (2-arachidonyl glyceryl ether, 2-AGE, 1) were synthesized and tested for their interaction with CB1 receptors in rat brain membranes. The results showed that a C-20 tetra-unsaturated moiety is necessary for high affinity, and that a series of alkyl glyceryl ethers of potential occurrence in brain tissues have less affinity than 2-AGE for CB1 receptors.

Stereospecific and regioselective opening of an oxirane system. A new efficient entry to 1- or 3-monoacyl- and 1- or 3-monoalkyl-sn-glycerols

Acyl or alkyl glycidols in the presence of trifluoroacetic anhydride (TFAA) and trifluoroacetate anions, undergo a regioselective and stereospecific opening of the oxirane system to produce the bis(trifluoroacetylated) derivatives, from which the corresponding 1(3)-monoacyl-sn-glycerols or 1(3)-monoalkyl-sn-glycerols can be obtained directly in high purity (>99%) and in quantitative yields.

ENANTIOMERE DER 2,2'-DINITROBIPHENYL-6,6'-DICARBONSAEURE ALS STEREOSELEKTIV WIRKSAME, REVERSIBLE SCHUTZGRUPPEN-II. STEREOSELEKTIVE SYNTHESEN VON LIPIDGRUNDKOERPERN ODER -BAUSTEINEN

S-(-)-1,1'-diphenyl-2,2'-dinitro-6,6'-dicarboxylic acid (1) is used as an axial-chiral protecting group for the primary hydroxy group of glycerol and glycerol derivatives.Diesters of 1 were formed which have the largest distance between the nitro groups and the nucleophilic substituents on glycerol.After hydrogenolytical removal of the protecting group asymmetric glycerol derivatives were obtained with approximately 10percent enantiomeric excess.Hydroxybromination of 12 resulted mainly in he anti-Markovnikov 13a instead of the Markovnikov product 13b expected, which was present only in traces.This deviation is discussed.

Method for preventing cancer metastasis

The present invention relates to the use of a specific family of glycerolipid compounds of formula (I) described in the detailed description or the manufacture of a medicament for the prevention or for the treatment of cancer metastasis.

Autotaxin structure-activity relationships revealed through lysophosphatidylcholine analogs

Autotaxin (ATX) catalyzes the hydrolysis of lysophosphatidylcholine (LPC) to form the bioactive lipid lysophosphatidic acid (LPA). LPA stimulates cell proliferation, cell survival, and cell migration and is involved in obesity, rheumatoid arthritis, neuropathic pain, atherosclerosis and various cancers, suggesting that ATX inhibitors have broad therapeutic potential. Product feedback inhibition of ATX by LPA has stimulated structure-activity studies focused on LPA analogs. However, LPA displays mixed mode inhibition, indicating that it can bind to both the enzyme and the enzyme-substrate complex. This suggests that LPA may not interact solely with the catalytic site. In this report we have prepared LPC analogs to help map out substrate structure-activity relationships. The structural variances include length and unsaturation of the fatty tail, choline and polar linker presence, acyl versus ether linkage of the hydrocarbon chain, and methylene and nitrogen replacement of the choline oxygen. All LPC analogs were assayed in competition with the synthetic substrate, FS-3, to show the preference ATX has for each alteration. Choline presence and methylene replacement of the choline oxygen were detrimental to ATX recognition. These findings provide insights into the structure of the enzyme in the vicinity of the catalytic site as well as suggesting that ATX produces rate enhancement, at least in part, by substrate destabilization.

Sarcoglycosides A-C, new O-glycosylglycerol derivatives from the South China sea soft coral Sarcophyton infundibuliforme

Chemical examination of the soft coral Sarcophyton infundibuliforme collected from the South China Sea resulted in the isolation of the three new O-glycosylglycerol derivatives sarcoglycosides A-C (1 - 3), together with two known compounds, chimyl alcohol

Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides

A trifluoroacetate-catalyzed opening of the oxirane ring of glycidyl derivatives bearing allylic acyl or alkyl functionalities with trifluoroacetic anhydride (TFAA), provides an efficient entry to configurationally homogeneous 1(3)-acyl- or 1(3)-O-alkyl-sn-glycerols. Selective introduction of tert-butyldimethylsilyl- (TBDMS), or triisopropylsilyl- (TIPS) transient protections at the terminal sites within these key intermediates secures 1(3)-acyl- or 1(3)-O-alkyl-3(1)-O-TBDMS (or TIPS)-sn-glycerols as general bifunctional precursors to 1,2(2,3)-diacyl-, 1(3)-O-alkyl-2-acyl- and 1,3-diacyl-sn-glycerols and hence triester isosters. Incorporation of a requisite acyl residue at the central carbon of the silylated synthons with a subsequent Et3N·3HF-promoted, direct trichloroacetylation across the siloxy system by trichloroacetic anhydride (TCAA), followed by cleavage of the trichloroacetyl group, affords the respective 1,2(2,3)-diacyl- or 1(3)-O-alkyl-2-acyl-sn-glycerols. Alternatively, a reaction sequence involving: (i) attachment of a trichloroacetyl fragment at the stereogenic C2-centre of the monosilylated glycerides; (ii) replacement of the silyl moiety by a short- or long-chain carboxylic acid residue by means of the acylating agent: tetra-n-butylammonium bromide (TBABr)-carboxylic acid anhydride (CAA)-trimethylsilyl bromide (TMSBr); and (iii) removal of the trichloroacetyl replacement, provides pure 1,3-diacyl-sn-glycerols. The TBABr-CAA-TMSBr reagent system allows also a one-step conversion of 1,2-diacylglycerol silyl ethers into homochiral triglycerides with predefined asymmetry and degree of unsaturation. These compounds can also be accessed via a two-step one-pot approach where the trichloroacetyl derivatives of 1,2(2,3)- or 1,3-diacyl-sn-glycerols serve as triester building blocks for establishing the third ester bond at preselected C3(1)- or C2-positions within the glycerol skeleton at the very last synthetic stage. In all instances, the target compounds were produced under mild conditions, in high enantiomeric purity, and in practically quantitative yields. The Royal Society of Chemistry 2007.

Methods employing and compositions containing defined oxidized phospholipids for prevention and treatment of atherosclerosis

Novel synthetic forms of etherified oxidized phospholipids and methods of utilizing same for preventing and treating atherosclerosis and other related disorders, as well as inflammatory disorders, immune mediated diseases, autoimmune diseases and proliferative disorders, are provided. In addition, methods of synthesizing etherified and esterified oxidized phospholipids and of using same for preventing and treating atherosclerosis and other related disorders are also provided.

Self-organizing properties of natural and related synthetic glycolipids

In this article we report on the syntheses, self-organizing properties, and structures of a variety of cerebrosides and related synthetic glycolipids. The thermotropic and lyotropic liquid crystalline properties of the materials were evaluated in detail. All of the families of materials studied exhibited columnar mesophases. In the dry state the aliphatic chains were found to be located on the exterior of the columns, whereas in the wet state the reverse was the case with the polar headgroups on the exterior. Thus, the aliphatic chains act almost like hydrocarbon solvents in the dry state.