EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

beta-hydroxymyristic acid
tetradecanoic acid, 3-hydroxy-

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Name:3-hydroxytetradecanoic acid
CAS Number: 1961-72-4Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J61.335E
Beilstein Number:1725372
MDL:MFCD00059633
XlogP3-AA:4.70 (est)
Molecular Weight:244.37476000
Formula:C14 H28 O3
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
TCI AMERICA
For experimental / research use only.
3-Hydroxymyristic Acid >98.0%(GC)(T)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :16064
National Institute of Allergy and Infectious Diseases:Data
3-hydroxytetradecanoic acid
Chemidplus:0001961724
 
References:
 3-hydroxytetradecanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):16064
Pubchem (sid):134982019
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
Golm Metabolome Database:Search
HMDB (The Human Metabolome Database):HMDB61656
Export Tariff Code:2918.19.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
3-hydroxymyristic acid
3-hydroxytetradecanoic acid
beta-hydroxytetradecanoic acid
 tetradecanoic acid, 3-hydroxy-
 

Articles:

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.
 
Notes:
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