beta-hydroxymyristic acid

tetradecanoic acid, 3-hydroxy-

CAS: 1961-72-4 C14 H28 O3 MW: 244.37476000

Identification

Namebeta-hydroxymyristic acid
IUPAC3-hydroxytetradecanoic acid
CAS Number1961-72-4
FDA UNIISearch
Molecular FormulaC14 H28 O3
Molecular Weight244.37476000
MDL NumberMFCD00059633
Nikkaji NumberJ61.335E
Beilstein1725372

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 SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for beta-hydroxymyristic acid usage levels up tonot for fragrance use.
Recommendation for beta-hydroxymyristic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

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 A 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.