Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H34O2 |
| Molecular Weight | 270.4507 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCC(=O)OC
InChI
InChIKey=FLIACVVOZYBSBS-UHFFFAOYSA-N
InChI=1S/C17H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19-2/h3-16H2,1-2H3
| Molecular Formula | C17H34O2 |
| Molecular Weight | 270.4507 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Methyl palmitate is one of endogenous fatty acid methyl esters. It has been demonstrated that methyl palmitate inhibited phagocytic activity and the effect was accompanied by differential expression of cytokines, nitric oxide, and COX-2. In addition, the in vitro and in vivo studies demonstrated that methyl palmitate has the potential to inhibit macrophages in general and also has promising anti-inflammatory and anti-fibrotic effects. The drug was tested in vivo on preclinical models of epidural fibrosis, asthma, pulmonary fibrosis, liver fibrosis and edema.
Approval Year
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/22842335 |
Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Anti-inflammatory and antifibrotic effects of methyl palmitate. | 2011-08-01 |
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| Identification of compounds in the essential oil of nutmeg seeds (Myristica fragrans Houtt.) that inhibit locomotor activity in mice. | 2010-11-23 |
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| Palmitate and insulin synergistically induce IL-6 expression in human monocytes. | 2010-11-05 |
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| Variations in fatty acid compositions of the seed oil of Eruca sativa Mill. caused by different sowing periods and nitrogen forms. | 2010-10 |
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| Methyl palmitate: a potent vasodilator released in the retina. | 2010-09 |
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| Assessment of the contact toxicity of methyl palmitate on Tetranychus viennensis (Acari: Tetranychidae). | 2010-08 |
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| Biosynthesis of unusual moth pheromone components involves two different pathways in the navel orangeworm, Amyelois transitella. | 2010-05 |
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| Marine diatom, Navicula sp. strain JPCC DA0580 and marine green alga, Chlorella sp. strain NKG400014 as potential sources for biodiesel production. | 2010-05 |
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| Marine drugs from sponge-microbe association--a review. | 2010-04-22 |
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| The tropical brown alga Lobophora variegata: a source of antiprotozoal compounds. | 2010-04-16 |
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| Ethnobotanical survey and cytotoxicity testing of plants of South-western Nigeria used to treat cancer, with isolation of cytotoxic constituents from Cajanus cajan Millsp. leaves. | 2010-03-24 |
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| Chlamydomonas as a "new" organism for biodiesel production. | 2010-03 |
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| Antimicrobial activities of essential oil and hexane extract of Florence fennel [Foeniculum vulgare var. azoricum (Mill.) Thell.] against foodborne microorganisms. | 2010-02 |
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| Antioxidant effects of ethyl acetate extract of Desmodium gangeticum root on myocardial ischemia reperfusion injury in rat hearts. | 2010-01-22 |
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| Interleukin-6 and Cyclooxygenase-2 downregulation by fatty-acid fractions of Ranunculus constantinopolitanus. | 2009-11-16 |
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| Lotus (Nelumbo nuficera) flower essential oil increased melanogenesis in normal human melanocytes. | 2009-07-31 |
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| Fibrinolytic compounds isolated from a brown alga, Sargassum fulvellum. | 2009-04-09 |
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| Time- and dose-related effects of di-(2-ethylhexyl) phthalate and its main metabolites on the function of the rat fetal testis in vitro. | 2009-04 |
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| Effect of additives in aqueous formulation on the foliar uptake of dimethomorph by cucumbers. | 2009-04 |
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| Methyl palmitate, an acaricidal compound occurring in green walnut husks. | 2009-02 |
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| Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods. | 2009-02 |
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| Olfactory perception of oviposition-deterring fatty acids and their methyl esters by the Asian corn borer, Ostrinia furnacalis. | 2009 |
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| Glycine and glycine receptor signalling in non-neuronal cells. | 2009 |
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| Methyl palmitate prevents CCl(4)-induced liver fibrosis. | 2008-11 |
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| Antileukemic effects of Didemnum psammatodes (Tunicata: Ascidiacea) constituents. | 2008-11 |
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| Structure-activity relationship of immunostimulatory effects of phthalates. | 2008-10-31 |
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| Prion infected meat-and-bone meal is still infectious after biodiesel production. | 2008-08-13 |
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| [Determination of 11 fatty acids and fatty acids methyl esters in biodiesel using ultra performance liquid chromatography]. | 2008-07 |
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| 16-Cyclopentadienyl tricarbonyl 99mTc 16-oxo-hexadecanoic acid: synthesis and evaluation of fatty acid metabolism in mouse myocardium. | 2008-06-26 |
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| Characterization of chemical components in extracts from Si-wu decoction with proliferation-promoting effects on rat mesenchymal stem cells. | 2008-05-01 |
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| Cyclooxygenase-2 inhibitory effects and composition of the volatile oil from the dried roots of Lithospermum erythrorhizon. | 2008-04 |
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| Temperature- and pH-induced structural changes in the membrane of the hyperthermophilic archaeon Aeropyrum pernix K1. | 2007-10 |
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| Lipase-catalyzed regioselective synthesis of steryl (6'-O-acyl)glucosides. | 2007-09 |
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| Exudation of allelopathic substances in buckwheat (Fagopyrum esculentum Moench). | 2007-08-08 |
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| Growing hot pepper for cabbage looper, Trichopulsia ni (Hübner) and spider mite, Tetranychus urticae (Koch) control. | 2007-06-15 |
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| The structure of OMCI, a novel lipocalin inhibitor of the complement system. | 2007-06-08 |
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| Gas chromatographic/mass spectrometric analysis of the essential oil of Houttuynia cordata Thunb by using on-column methylation with tetramethylammonium acetate. | 2007-03-22 |
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| Fluxome analysis using GC-MS. | 2007-02-07 |
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| Does lipophilicity per se induce adjuvant effects? Methyl palmitate as model substance does not affect ovalbumin sensitization. | 2007-01-15 |
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| Fatty acid composition of Abies pindrow (West Himalayan fir). | 2007-01 |
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| New amphiphilic diblock copolymers: surfactant properties and solubilization in their micelles. | 2006-04-25 |
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| Study on the antiinflammatory activity of methanol extract from seagrass Zostera japonica. | 2006-01-25 |
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| Methyl palmitate inhibits lipopolysaccharide-stimulated phagocytic activity of rat peritoneal macrophages. | 2006 |
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| An infrared spectroscopic method for quantitative analysis of fatty alcohols and fatty acid esters in machinery oils. | 2005-09 |
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| Benefit of Kupffer cell modulation with glycine versus Kupffer cell depletion after liver transplantation in the rat: effects on postischemic reperfusion injury, apoptotic cell death graft regeneration and survival. | 2005-09 |
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| Methyl palmitate: inhibitor of phagocytosis in primary rat Kupffer cells. | 2005-06-01 |
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| Presence and titer of methyl palmitate in the Medfly (Ceratitis capitata) during reproductive maturation. | 2005-04 |
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| Regioselective acylation of flavonoids catalyzed by immobilized Candida antarctica lipase under reduced pressure. | 2004-07 |
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| Influence of DnaK and DnaJ chaperones on Escherichia coli membrane lipid composition. | 2004 |
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| Action of 1-isonicotinyl-2-palmitoyl hydrazine against the Mycobacterium avium complex and enhancement of its activity by m-fluorophenylalanine. | 1990-11 |
Patents
Sample Use Guides
In a preclinical model of epidural fibrosis, methyl palmitate (300 mg/kg) was given orally three times per week on different days for a total period of 4 weeks. In a preclinical model of asthma and pulmonary fibrosis, methyl palmitate (300mg/kg) was given intraperitoneally three times per week in the last four weeks of the study period. In a model of liver fibrosis, methyl palmitate (300 mg/kg)was given intraperitoneally, daily.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15840433
In MTT cytotoxicity assay, Primary rat Kupffer cells were treated with 0.5, 1, and 2 mM methyl palmitate for 24 h followed by with 20 uL MTT (0.5% in PBS) for 4.5 h. In phagocytosis activity assay, cells were treated with 0.5 mM methyl palmitate for 0.5, 1, 2, 4, and 6 h (time-dependent assay) or with methyl palmitate (0.25, 0.5, and 1 mM) for 24 h followed by LPS (500 ng/ml) stimulation for 6 h (dose-dependent assay). Cell viability, as determined by MTT assay, decreased significantly at 2 mM methyl palmitate while changes at 0.5 and 0.1 mM were insignificant. The phagocytic activity of Kupffer cells decreased significantly at all the MP concentration tested when cells were incubated with methyl palmitate for 24 h followed by LPS treatment for 6 h
| Substance Class |
Chemical
Created
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admin
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Edited
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| Record UNII |
DPY8VCM98I
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| Record Status |
Validated (UNII)
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| Record Version |
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