beta-hydroxymyristic acid
tetradecanoic acid, 3-hydroxy-
Identification
| Name | beta-hydroxymyristic acid |
| IUPAC | 3-hydroxytetradecanoic acid |
| CAS Number | 1961-72-4 |
| FDA UNII | Search |
| Molecular Formula | C14 H28 O3 |
| Molecular Weight | 244.37476000 |
| MDL Number | MFCD00059633 |
| Nikkaji Number | J61.335E |
| Beilstein | 1725372 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 376.90 °C. @ 760.00 mm Hg (est) |
| Flash Point | 385.00 °F. TCC ( 195.90 °C. ) (est) |
| logP (o/w) | 4.180 (est) |
| Soluble in | water, 17.82 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for beta-hydroxymyristic acid usage levels up to | not for fragrance use. |
| Recommendation for beta-hydroxymyristic acid flavor usage levels up to | not for flavor use. |
Potential Uses
Natural Occurrence
Synonyms
3-
hydroxymyristic acid
3-
hydroxytetradecanoic acid
beta-
hydroxytetradecanoic acid
tetradecanoic acid, 3-hydroxy-
PubMed:
Mitochondrial bioenergetics deregulation caused by long-chain 3-hydroxy fatty acids accumulating in LCHAD and MTP deficiencies in rat brain: a possible role of mPTP opening as a pathomechanism in these disorders?
PubMed:
Alteration of the phenotypic and pathogenic patterns of Burkholderia pseudomallei that persist in a soil environment.
PubMed:
Production of medium-chain-length 3-hydroxyalkanoic acids by β-oxidation and phaC operon deleted Pseudomonas entomophila harboring thioesterase gene.
PubMed:
[Sulfated polysaccharides of brown seaweeds--ligands of toll-like receptors].
PubMed:
[Biological activity of Budvicia aquatica lipopolysaccharides].
PubMed:
Functional characterization of an NADPH dependent 2-alkyl-3-ketoalkanoic acid reductase involved in olefin biosynthesis in Stenotrophomonas maltophilia.
PubMed:
The effects of hydroxy fatty acids on the hyphal branching of germinated spores of AM fungi.
PubMed:
Structural features of lipid AÂ of Rickettsia typhi.
PubMed:
Functional dissection of surfactin synthetase initiation module reveals insights into the mechanism of lipoinitiation.
PubMed:
Disturbance of mitochondrial energy homeostasis caused by the metabolites accumulating in LCHAD and MTP deficiencies in rat brain.
PubMed:
Long-chain 3-hydroxy fatty acids accumulating in LCHAD and MTP deficiencies induce oxidative stress in rat brain.
PubMed:
[Chemical characterisation of structural components of Rahnella aquatilis lipopolysaccharides].
PubMed:
Crystal structure and acyl chain selectivity of Escherichia coli LpxD, the N-acyltransferase of lipid A biosynthesis.
PubMed:
Identification of light-independent inhibition of human immunodeficiency virus-1 infection through bioguided fractionation of Hypericum perforatum.
PubMed:
Use of Fatty Acid Methyl Ester Profiles to Compare Copper-Tolerant and Copper-Sensitive Strains of Pantoea ananatis.
PubMed:
Structural features of lipid A of Piscirickettsia salmonis, the etiological agent of the salmonid rickettsial septicemia.
PubMed:
Production and characterization of medium-chain-length polyhydroxyalkanoate with high 3-hydroxytetradecanoate monomer content by fadB and fadA knockout mutant of Pseudomonas putida KT2442.
PubMed:
Rhizobium etli CE3 bacteroid lipopolysaccharides are structurally similar but not identical to those produced by cultured CE3 bacteria.
PubMed:
The evaluation of the role of beta-hydroxy fatty acids on chronic inflammation and insulin resistance.
PubMed:
[The structural diversity of lipid A from gram-negative bacteria].
PubMed:
Determination of the profile of fatty acids of 4 species of Shigella spp by chromatography of gases.
PubMed:
Structural characterization of the lipid A region of Aeromonas salmonicida subsp. salmonicida lipopolysaccharide.
PubMed:
Complete lipopolysaccharide of Plesiomonas shigelloides O74:H5 (strain CNCTC 144/92). 2. Lipid A, its structural variability, the linkage to the core oligosaccharide, and the biological activity of the lipopolysaccharide.
PubMed:
[Analysis of the impurity of bacterium source of standard endotoxin by gas chromatography/mass spectrometry].
PubMed:
Biosynthesis of medium-chain-length poly(hydroxyalkanoates) from soy molasses.
PubMed:
Structural characterization of lipid A from nontypeable and type f Haemophilus influenzae: variability of fatty acid substitution.
PubMed:
Tobacco smoking increases dramatically air concentrations of endotoxin.
PubMed:
Initiation of surfactin biosynthesis and the role of the SrfD-thioesterase protein.
PubMed:
Interaction of porin from Yersinia pseudotuberculosis with different structural forms of endogenous lipopolysaccharide.
PubMed:
A process in need is a process indeed: scalable enantioselective synthesis of chiral compounds for the pharmaceutical industry.
PubMed:
Glucose/lipid mixed substrates as a means of controlling the properties of medium chain length poly(hydroxyalkanoates).
PubMed:
Structural and biological characterisation of a novel tetra-acyl lipid A from Escherichia coli F515 lipopolysaccharide acting as endotoxin antagonist in human monocytes.
PubMed:
Detoxification of endotoxin by endodontic irrigants and calcium hydroxide.
PubMed:
Accumulation of free 3-hydroxy fatty acids in the culture media of fibroblasts from patients deficient in long-chain l-3-hydroxyacyl-CoA dehydrogenase: a useful diagnostic aid.
PubMed:
Effects of culture method and growth phase on free lipid composition of Yersinia pseudotuberculosis.
PubMed:
Isolation and structural characterization of an R-form lipopolysaccharide from Yersinia enterocolitica serotype O:8.
PubMed:
Characterization of a novel lipid A containing D-galacturonic acid that replaces phosphate residues. The structure of the lipid a of the lipopolysaccharide from the hyperthermophilic bacterium Aquifex pyrophilus.
PubMed:
Structure of the lipid A of Bordetella hinzii ATCC 51730.
PubMed:
Occurrence of the toxin dehydroabietic acid in Salmonella typhimurium.
PubMed:
Characterization of the ybdT gene product of Bacillus subtilis: novel fatty acid beta-hydroxylating cytochrome P450.
PubMed:
Clinical and veterinary isolates of Salmonella enterica serovar enteritidis defective in lipopolysaccharide O-chain polymerization.
PubMed:
[Estimation of mean molecular weight of Enterobacteriaceae lipopolysaccharides using gas chromatography for determination of fatty acids].
PubMed:
Phenotypic and genotypic characterization of clinical strains of CDC group IVc-2.
PubMed:
Identification of a novel heptoglycan of alpha1-->2-linked D-glycero-D-manno-heptopyranose. Chemical and antigenic structure of lipopolysaccharides from Klebsiella pneumoniae ssp. pneumoniae rough strain R20 (O1-:K20-).
PubMed:
Mutation of the htrB gene in a virulent Salmonella typhimurium strain by intergeneric transduction: strain construction and phenotypic characterization.
PubMed:
Chemical and biological properties of lipopolysaccharide from Selenomonas sputigena ATCC 33150.
PubMed:
Biochemical characterization of lipopolysaccharides extracted from a hydrophobic strain of Pasteurella multocida.
PubMed:
Study on surfactin, a cyclic depsipeptide. II. Synthesis of surfactin B2 produced by Bacillus natto KMD 2311.
PubMed:
Lipopolysaccharide determination by reversed-phase high-performance liquid chromatography after fluorescence labeling.
PubMed:
Synthesis and mitogenic activity of nonreducing-sugar subunit analogs of bacterial lipid A composed only of 3-hydroxytetradecanoic acid and its homologs.
PubMed:
Lipopolysaccharides of Actinobacillus pleuropneumoniae bind pig hemoglobin.
PubMed:
O-antigenic lipopolysaccharide of Vibrio cholerae O139 Bengal, a new epidemic strain for recent cholera in the Indian subcontinent.
PubMed:
Specificity of rabbit antisera against the rough lipopolysaccharide of Salmonella minnesota strain R7 (chemotype Rd1P-).
PubMed:
Specificity of rabbit antisera against the rough lipopolysaccharide of Salmonella minnesota R4 (chemotype Rd2P-)
PubMed:
Chemical structure of the lipid A of Escherichia coli J-5.
PubMed:
Defective biosynthesis of the lipid A component of temperature-sensitive firA (omsA) mutant of Escherichia coli.
PubMed:
UDP-N-acetylglucosamine 3-O-acyltransferase from Escherichia coli.
PubMed:
Structural analysis of the lipid A component of Campylobacter jejuni CCUG 10936 (serotype O:2) lipopolysaccharide. Description of a lipid A containing a hybrid backbone of 2-amino-2-deoxy-D-glucose and 2,3-diamino-2,3-dideoxy-D-glucose.
PubMed:
Endotoxin shedding by enterobacteria: free and cell-bound endotoxin differ in Limulus activity.
PubMed:
Bile increases lipopolysaccharide release in experimental E. coli peritonitis.
PubMed:
Biophysical alteration of lung surfactant by extracts of cotton dust.
PubMed:
Structure of syringotoxin, a bioactive metabolite of Pseudomonas syringae pv. syringae.
PubMed:
[Studies on resistant mechanisms in the resistant bacteria to chlorhexidine. II. Chemical components of the cell membrane and the electron microscopical observation of cell surface structure of chlorhexidine-resistant bacteria].
PubMed:
Antiendotoxin activity of lipid A analogues: requirements of the chemical structure.
PubMed:
Development of a new quantitative method for detection of endotoxin by fluorescence labeling of 3-hydroxy fatty acid.
PubMed:
Lipid a component of Salmonella typhimurium carrying the derepressed Col Ib plasmids.
PubMed:
The structure of syringomycins A1, E and G.
PubMed:
Epitope specificities of murine monoclonal and rabbit polyclonal antibodies against enterobacterial lipopolysaccharides of the Re chemotype.
PubMed:
Deacylation of bacterial lipopolysaccharide in rat hepatocytes in vitro.
PubMed:
Studies on the antigenic S-type lipopolysaccharides of Brucella abortus strains 7 and Mustapha.
PubMed:
Studies on the chemical constitution of cell wall lipo-oligosaccharide from Campylobacter coli Labet 227.
PubMed:
Two-dimensional gas chromatography with electron-capture detection used in the determination of specific peptidoglycan and lipopolysaccharide constituents of gram-negative bacteria in infected human urine.
PubMed:
Fatty acid composition of lipopolysaccharides of the strains of different species of Yersinia.
PubMed:
Isolation of a mutant from Salmonella typhimurium producing acyl-deficient lipopolysaccharides.
PubMed:
Chemical structure of the lipopolysaccharide of Haemophilus influenzae strain I-69 Rd-/b+. Description of a novel deep-rough chemotype.
PubMed:
3-Hydroxymyristic acid as a measure of endotoxin in cotton lint and dust.
PubMed:
[Antigenic polysaccharides of bacteria of the genus Shigella. Determination of the structure of polysaccharide chains of Shigella boydii type 9 lipopolysaccharide and detection of unusually high molecular weight glycolipid].
PubMed:
Determination of endotoxins by gas chromatography: evaluation of electron-capture and negative-ion chemical-ionization mass spectrometric detection of halogenated derivatives of beta-hydroxymyristic acid.
PubMed:
[Studies on endotoxins of Leptospira. III. The presence of beta-hydroxy-myristic acid in the LPS of Leptospira interrogans serovar Lai].
PubMed:
Synthesis of the optically active 4-O-phosphono-D-glucosamine derivatives related to the nonreducing-sugar subunit of bacterial lipid A.
PubMed:
Differentiation of Campylobacter and Campylobacter-like organisms by cellular fatty acid composition.
PubMed:
Heterogeneity of lipid A: structural determination by 13C and 31P NMR of lipid A fractions from lipopolysaccharide of Escherichia coli 0111.
PubMed:
Tumor necrosis factor (cachectin) is an endogenous pyrogen and induces production of interleukin 1.
PubMed:
Synthesis of 2-deoxy-4-O-phosphono-3-O-tetradecanoyl-2-[(3R)- and (3S)-3-tetradecanoyloxytetradecanamido]-D-glucose: a diastereoisomeric pair of 4-O-phosphono-D-glucosamine derivatives (GLA-27) related to bacterial lipid A.
PubMed:
Structure-activity relationship of lipid A: comparison of biological activities of natural and synthetic lipid A's with different fatty acid compositions.
PubMed:
Modification of the chemical composition and structure of the U.S. Reference Standard Endotoxin (RSE) by 60Co radiation.
PubMed:
The fatty acid content of the Bordetella pertussis endotoxin.
PubMed:
Method for detecting the 3-hydroxymyristic acid component of the endotoxins of gram-negative bacteria in compost samples.
PubMed:
Isolation and composition of sheathed flagella from Bdellovibrio bacteriovorus 109J.
PubMed:
[Synthesis of lipid A analogs. Obtaining conjugates of 6-phosphate 2-desoxy-2-(3-hydroxymyristoyl)amino-D-glucose with polymer carriers and their immunological properties].
PubMed:
Isolation and structural analysis of two lipid A precursors from a KDO deficient mutant of Salmonella typhimurium differing in their hexadecanoic acid content.
PubMed:
Fatty acid composition and Shwartzman activity of lipopolysaccharides from oral bacteria.
PubMed:
Structural studies on the lipid A component of enterobacterial lipopolysaccharides by laser desorption mass spectrometry. Location of acyl groups at the lipid A backbone.
PubMed:
Chemical and immunological characterization of lipopolysaccharides from phase I and phase II Coxiella burnetii.
PubMed:
Chemical studies of partially hydrolysed lipopolysaccharides from four strains of Campylobacter jejuni and two strains of Campylobacter coli.
PubMed:
Concepts of the chemical structure of lipid A.
PubMed:
Composition of O-antigenic lipopolysaccharides from Enterobacter cloacae.
PubMed:
Structural studies on the phosphate-free lipid A of Rhodomicrobium vannielii ATCC 17100.
PubMed:
Chemical structure of the lipid A component of the lipopolysaccharide from a Proteus mirabilis Re-mutant.
PubMed:
Enzymatic deacylation of the lipid A moiety of Salmonella typhimurium lipopolysaccharides by human neutrophils.
PubMed:
Nontoxic lipopolysaccharide from Rhodopseudomonas sphaeroides ATCC 17023.
PubMed:
Acylpeptides, the inhibitors of cyclic adenosine 3',5'-monophosphate phosphodiesterase. I. Purification, physicochemical properties and structures of fatty acid residues.
PubMed:
Immunochemical studies on Brucella abortus lipopolysaccharides.
PubMed:
Fatty acid in lipopolysaccharides of Salmonella species grown at low temperature. Identification and position.
PubMed:
Proteins from Salmonella R-mutants mediating protection against Salmonella typhimurium infection in mice I. Preparation of proteins free from lipopolysaccharide using various chromatographic methods.
PubMed:
A surface polysaccharide of Escherichia coli O111 contains O-antigen and inhibits agglutination of cells by O-antiserum.
PubMed:
The chemical structure of lipid A. Demonstration of amide-linked 3-acyloxyacyl residues in Salmonella minnesota Re lipopolysaccharide.
PubMed:
Isolation and chemical composition of lipopolysaccharide from Campylobacter jejuni.
PubMed:
The hepatocellular uptake and biliary excretion of endotoxin in the rat.
PubMed:
The chemical structure of the lipid A component of lipopolysaccharides from Vibrio cholerae.
PubMed:
Comparison of human urine gastric inhibitor (HUGI) and bacterial endotoxin as inhibitors of acid secretion.
PubMed:
Cellular fatty acid composition of Campylobacter fetus.
PubMed:
Extraction, distribution and biodegradation of bacterial lipopolysaccharides in estuarine sediments.
PubMed:
Structural studies on the immunodominant group of lipid A from lipopolysaccharide of Yersinia pseudotuberculosis.
PubMed:
Isolation, characterization, and biological properties of an endotoxin-like material from the gram-positive organism Listeria monocytogenes.
PubMed:
Chemical characterization and biological properties of lipopolysaccharides isolated from smooth and rough strains of Brucella abortus.
PubMed:
Immunochemical characterization of surface antigens of Bacteroides melaninogenicus.
PubMed:
Degradation of bacterial lipopolysaccharide by the slime mould Physarum polycephalum.
PubMed:
Characterization of endotoxin from the rumen bacterium Megasphaera elsdenii.
PubMed:
Determination of lipid A and endotoxin in serum by mass spectroscopy.
PubMed:
L-2-hydroxytetradecanoic acid as a constituent of Salmonella lipopolysaccharides (lipid A).
PubMed:
Radiation induced alterations in the endotoxin of S. typhimurium.
PubMed:
Composition of the lipopolysaccharide of Neisseria gonorrhoeae.
PubMed:
Chemical structure of the lipid A component of lipopolysaccharides from Fusobacterium nucleatum.
PubMed:
[Investigations on the fatty acid composition of lipids from Salmonella minnesota S and R forms (author's transl)].
PubMed:
Isolation and characterization of the lipopolysaccharide of Chromatium vinosum.
PubMed:
Phospholipid and lipopolysaccharide in Proteus mirabilis and its stable protoplast L-form. Difference in content and fatty acid composition.
PubMed:
Modification of resistance of mice to Naegleria fowleri infections.
PubMed:
Endotoxic activity of complexes of myristic acid and proteins.
PubMed:
Lipophilic O-antigens containing D-glycero-D-mannoheptose as the sole neutral sugar in Rhodopseudomonas gelatinosa.
PubMed:
Physical and chemical studies of Thiobacillus ferroxidans lipopolysaccharides.
PubMed:
Chemical studies on damages of Escherichia coli by the immune bactericidal reaction. I. Release and degradation of phospholipids from damaged bacteria.
PubMed:
Isolation and characterization of 2-keto-3-deoxyoctonate-lipid A from a heptose-deficient mutant of Escherichia coli.
PubMed:
The chemical composition of the lipopolyacarideof Pseudomonas aeruginosa.
PubMed:
Indentification and localization of the fatty acids in Haemophilus parainfluenzae.
PubMed:
Chemical and biological properties of an extracellular lipopolysaccharide from Escherichia coli grown under lysine-limiting conditions.