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tuberculostearic acid
octadecanoic acid, 10-methyl-

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CAS Number: 542-47-2Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J108.049K
XlogP3:7.70 (est)
Molecular Weight:298.51026000
Formula:C19 H38 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 415.00 to 416.00 °C. @ 760.00 mm Hg (est)
Flash Point: 454.00 °F. TCC ( 234.50 °C. ) (est)
logP (o/w): 8.184 (est)
Soluble in:
 water, 0.002247 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Tuberculostearic Acid
 
Safety Information:
 
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 tuberculostearic acid usage levels up to:
 not for fragrance use.
 
Recommendation for tuberculostearic 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 :65037
National Institute of Allergy and Infectious Diseases:Data
10-methyloctadecanoic acid
Chemidplus:0000542472
 
References:
 10-methyloctadecanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):65037
Pubchem (sid):135023253
 
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
KEGG (GenomeNet):C16794
HMDB (The Human Metabolome Database):HMDB04085
FooDB:FDB023306
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
10-methyl octadecanoic acid
10-methyloctadecanoic acid
 octadecanoic acid, 10-methyl-
 stearic acid, 10-methyl-
 

Articles:

PubMed:A Scalable, Non-enzymatic Synthesis of Highly Stereopure Difunctional C4 Secondary Methyl Linchpin Synthons.
PubMed:Corynebacterium atrinae sp. nov., isolated from the gastrointestinal tract of a pen shell, Atrina pectinata.
PubMed:Streptomyces bohaiensis sp. nov., a novel actinomycete isolated from Scomberomorus niphonius in the Bohai Sea.
PubMed:Tomitella cavernea sp. nov., an actinomycete isolated from soil.
PubMed:Rapid diagnosis of TB using GC-MS and chemometrics.
PubMed:Lipoproteins of slow-growing Mycobacteria carry three fatty acids and are N-acylated by apolipoprotein N-acyltransferase BCG_2070c.
PubMed:Expression and characterization of Rv0447c product, potentially the methyltransferase involved in tuberculostearic acid biosynthesis in Mycobacterium tuberculosis.
PubMed:Rapid determination of growth inhibition of Mycobacterium tuberculosis by GC-MS/MS quantitation of tuberculostearic acid.
PubMed:Biochemical characterization of an S-adenosyl-l-methionine-dependent methyltransferase (Rv0469) of Mycobacterium tuberculosis.
PubMed:Synthesis, structural elucidation, and biochemical analysis of immunoactive glucuronosyl diacylglycerides of mycobacteria and corynebacteria.
PubMed:Corynebacterium pyruviciproducens, as an immune modulator, can promote the activity of macrophages and up-regulate antibody response to particulate antigen.
PubMed:Micromonospora wenchangensis sp. nov., isolated from mangrove soil.
PubMed:Rudaeicoccus suwonensis gen. nov., sp. nov., an actinobacterium isolated from the epidermal tissue of a root of a Phalaenopsis orchid.
PubMed:Gordonia phosphorivorans sp. nov., isolated from a wastewater bioreactor with phosphorus removal.
PubMed:Gordonia caeni sp. nov., isolated from sludge of a sewage disposal plant.
PubMed:Corynebacterium pyruviciproducens promotes the production of ovalbumin specific antibody via stimulating dendritic cell differentiation and up-regulating Th2 biased immune response.
PubMed:Novel inhibitors of InhA efficiently kill Mycobacterium tuberculosis under aerobic and anaerobic conditions.
PubMed:Motilibacter peucedani gen. nov., sp. nov., isolated from rhizosphere soil.
PubMed:Williamsia phyllosphaerae sp. nov., isolated from the surface of Trifolium repens leaves.
PubMed:Corynebacterium nuruki sp. nov., isolated from an alcohol fermentation starter.
PubMed:Gordonia humi sp. nov., isolated from soil.
PubMed:Nocardiopsis nikkonensis sp. nov., isolated from a compost sample.
PubMed:Tomitella biformata gen. nov., sp. nov., a new member of the suborder Corynebacterineae isolated from a permafrost ice wedge.
PubMed:Nocardiopsis sinuspersici sp. nov., isolated from sandy rhizospheric soil.
PubMed:Nocardia mikamii sp. nov., isolated from human pulmonary infections in the USA.
PubMed:Identification of apolipoprotein N-acyltransferase (Lnt) in mycobacteria.
PubMed:A fast method for the identification of Mycobacterium tuberculosis in sputum and cultures based on thermally assisted hydrolysis and methylation followed by gas chromatography-mass spectrometry.
PubMed:Corynebacterium maris sp. nov., a marine bacterium isolated from the mucus of the coral Fungia granulosa.
PubMed:Corynebacterium lubricantis sp. nov., isolated from a coolant lubricant.
PubMed:Labedella gwakjiensis gen. nov., sp. nov., a novel actinomycete of the family Microbacteriaceae.
PubMed:Aeromicrobium panaciterrae sp. nov., isolated from soil of a ginseng field in South Korea.
PubMed:Synthesis and structure of phosphatidylinositol dimannoside.
PubMed:Smaragdicoccus niigatensis gen. nov., sp. nov., a novel member of the suborder Corynebacterineae.
PubMed:A new short synthesis of 10R-tuberculostearic acid and its enantiomer.
PubMed:Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis.
PubMed:Identification of a lipoarabinomannan-like lipoglycan in the actinomycete Gordonia bronchialis.
PubMed:Novel mycolic acid-containing bacteria in the family Segniliparaceae fam. nov., including the genus Segniliparus gen. nov., with descriptions of Segniliparus rotundus sp. nov. and Segniliparus rugosus sp. nov.
PubMed:A rapid method of diagnosing pulmonary tuberculosis using stir bar sorptive extraction-thermal desorption-gas chromatography-mass spectrometry.
PubMed:Nocardiopsis salina sp. nov., a novel halophilic actinomycete isolated from saline soil in China.
PubMed:Detection of tuberculostearic acid in serum and other biological fluids from patients with tuberculosis by electron capture-gas chromatography and chemical ionisation-mass spectrometry.
PubMed:Nocardioides ganghwensis sp. nov., isolated from tidal flat sediment.
PubMed:Nocardiopsis aegyptia sp. nov., isolated from marine sediment.
PubMed:Circulating tuberculostearic acid in tuberculosis patients.
PubMed:Aeromicrobium marinum sp. nov., an abundant pelagic bacterium isolated from the German Wadden Sea.
PubMed:Unique mechanism of action of the thiourea drug isoxyl on Mycobacterium tuberculosis.
PubMed:Gordonia paraffinivorans sp. nov., a hydrocarbon-degrading actinomycete isolated from an oil-producing well.
PubMed:Gordonia sihwensis sp. nov., a novel nitrate-reducing bacterium isolated from a wastewater-treatment bioreactor.
PubMed:Diagnosis of tuberculosis: available technologies, limitations, and possibilities.
PubMed:Phospholipid composition of several clinically relevant Corynebacterium species as determined by mass spectrometry: an unusual fatty acyl moiety is present in inositol-containing phospholipids of Corynebacterium urealyticum.
PubMed:Identification of three strains of Mycobacterium species isolated from clinical samples using fatty acid methyl ester profiling.
PubMed:Analysis of aminofluorescein-fatty acid derivatives by capillary electrophoresis with laser-induced fluorescence detection at the attomole level: application to mycobacterial fatty acids.
PubMed:Gordonia westfalica sp. nov., a novel rubber-degrading actinomycete.
PubMed:Apoptosis modulation by mycolic acid, tuberculostearic acid and trehalose 6,6'-dimycolate.
PubMed:Nocardiopsis compostus sp. nov., from the atmosphere of a composting facility.
PubMed:Nocardiopsis halotolerans sp. nov., isolated from salt marsh soil in Kuwait.
PubMed:Mycobacterium frederiksbergense sp. nov., a novel polycyclic aromatic hydrocarbon-degrading Mycobacterium species.
PubMed:Pseudonocardia kongjuensis sp. nov., isolated from a gold mine cave.
PubMed:Nocardia veterana sp. nov., isolated from human bronchial lavage.
PubMed:Revival of the genus Lentzea and proposal for Lechevalieria gen. nov.
PubMed:Electron-capture gas chromatographic-chemical ionization mass spectrometric study of sera from people vaccinated with bacille Calmette-Guerin for characteristic metabolites.
PubMed:Mycobacterium heckeshornense sp. nov., A new pathogenic slowly growing Mycobacterium sp. Causing cavitary lung disease in an immunocompetent patient.
PubMed:Marmoricola aurantiacus gen. nov., sp. nov., a coccoid member of the family Nocardioidaceae isolated from a marble statue.
PubMed:Gordonia polyisoprenivorans sp. nov., a rubber-degrading actinomycete isolated from an automobile tyre.
PubMed:Gordonia alkanivorans sp. nov., isolated from tar-contaminated soil.
PubMed:Williamsia muralis gen. nov., sp. nov., isolated from the indoor environment of a children's day care centre.
PubMed:Corynebacterium terpenotabidum sp. nov., a bacterium capable of degrading squalene.
PubMed:A new rapidly growing mycobacterial species, Mycobacterium murale sp. nov., isolated from the indoor walls of a children's day care centre.
PubMed:Corynebacterium confusum sp. nov., isolated from human clinical specimens.
PubMed:Gordonia rhizosphera sp. nov. isolated from the mangrove rhizosphere.
PubMed:Staphylococcus succinus sp. nov., isolated from Dominican amber.
PubMed:Development of a quantitative chemical ionization gas chromatography-mass spectrometry method to detect tuberculostearic acid in body fluids.
PubMed:Two new Mycobacterium strains and their role in toluene degradation in a contaminated stream.
PubMed:[Characterization of fatty acids and mycolic acid degradation products in mycobacterial species of major incidence in Argentina].
PubMed:The phosphatidyl-myo-inositol anchor of the lipoarabinomannans from Mycobacterium bovis bacillus Calmette Guérin. Heterogeneity, structure, and role in the regulation of cytokine secretion.
PubMed:Constitutive fatty acid and enzyme profiles of Mycobacterium species.
PubMed:Rapid chemotaxonomic diagnosis of human tuberculosis.
PubMed:Diagnostic performance of amplified Mycobacterium tuberculosis direct test with cerebrospinal fluid, other nonrespiratory, and respiratory specimens.
PubMed:The diagnostic value of tuberculostearic acid in tuberculous pleural effusions.
PubMed:Differentiation of sarcoidosis from tuberculosis by use of electron capture gas-liquid chromatography.
PubMed:Rhodococcus percolatus sp. nov., a bacterium degrading 2,4,6-trichlorophenol.
PubMed:[Determination of tuberculostearic acid for diagnosis of tuberculous meningitis with negative culture of tubercle bacillus].
PubMed:Gas chromatographic-mass spectrometric study of lipids and rapid diagnosis of Mycobacterium tuberculosis.
PubMed:Tests for detection and identification of mycobacteria. How should they be used?
PubMed:Lentzea gen. nov., a new genus of the order Actinomycetales.
PubMed:Transfer of polychlorophenol-degrading Rhodococcus chlorophenolicus (Apajalahti et al. 1986) to the genus Mycobacterium as Mycobacterium chlorophenolicum comb. nov.
PubMed:Synthesis of (R,S)-10-methyloctadecanoic acid (tuberculostearic acid) and key chiral 2-methyl branched intermediates.
PubMed:The diagnosis of pulmonary tuberculosis by gaschromatographic detection of tuberculostearic acid using flame ionisation detectors.
PubMed:[Detection of tuberculostearic acid (TBSA) in CSF using gas chromatography in patients with tuberculous meningitis].
PubMed:[Microbiological diagnosis of tuberculosis].
PubMed:Isolation and characterization of a novel glucuronosyl diacylglycerol from Mycobacterium smegmatis.
PubMed:Cellular fatty acid methyl ester profiles as a tool in the differentiation of members of the genus Mycobacterium.
PubMed:[Suprasellar space-occupying lesion as initial manifestation of tuberculosis in childhood].
PubMed:The laboratory diagnosis of mycobacterial diseases.
PubMed:Detection of 2-eicosanol by gas chromatography-mass spectrometry in sputa from patients with pulmonary mycobacterial infections.
PubMed:Low-energy tandem mass spectrometry of the molecular ion derived from fatty acid methyl esters: A novel method for analysis of branched-chain fatty acids.
PubMed:[Current methods in rapid diagnosis of tuberculosis].
PubMed:[Tuberculosis 1992: current clinical aspects, epidemiology and diagnosis].
PubMed:Effect of growth temperature on the fatty acid composition of Mycobacterium phlei.
PubMed:Lipid composition of leprosy-derived corynebacteria, a distinct group of corynebacteria, and of a reference Corynebacterium.
PubMed:An integrated procedure for the direct detection of characteristic lipids in tuberculosis patients.
PubMed:Application of gas chromatography-mass spectrometry for rapid detection of Mycobacterium xenopi in drinking water.
PubMed:Diagnosis of tuberculous pleural effusion by the detection of tuberculostearic acid in pleural aspirates.
PubMed:Evaluation of polymerase chain reaction, tuberculostearic acid analysis, and direct microscopy for the detection of Mycobacterium tuberculosis in sputum.
PubMed:Mycobacterium alvei sp. nov.
PubMed:Leprosy-derived chemoautotrophic nocardioform (CAN) bacteria closely resemble, or are identical with, Mycobacterium leprae on mycolate and other lipid profiles.
PubMed:Chemotaxonomic differentiation of coryneform bacteria isolated from biofilters.
PubMed:Simultaneous measurements of adenosine deaminase activity and tuberculostearic acid in pleural effusions for the diagnosis of tuberculous pleuritis.
PubMed:Bacteriological diagnosis of tuberculosis in children.
PubMed:Diagnosis of tuberculous meningitis by detection of tuberculostearic acid in cerebrospinal fluid.
PubMed:Bronchoscopy and tuberculostearic acid assay in the diagnosis of sputum smear-negative pulmonary tuberculosis: a prospective study with the addition of transbronchial biopsy.
PubMed:[The tuberculostearic acid study].
PubMed:Diagnosis of tuberculous pleural effusion by the detection of tuberculostearic acid in pleural aspirates.
PubMed:Mass spectrometry as a tool for identifying group D2 corynebacteria by their fatty acid profiles.
PubMed:False-positive tuberculostearic acid tests in cysticercosis.
PubMed:[Determination of tuberculostearic acid--progress in early diagnosis of tuberculous meningitis].
PubMed:Spatial distribution of microbial biomass, activity, community structure, and the biodegradation of linear alkylbenzene sulfonate (LAS) and linear alcohol ethoxylate (LAE) in the subsurface.
PubMed:Analysis of cellular fatty acids and proteins by capillary gas chromatography and sodium dodecyl sulphate polyacrylamide gel electrophoresis to differentiate Mycobacterium avium, Mycobacterium intracellulare and Mycobacterium scrofulaceum (MAIS) complex species.
PubMed:Taxonomic implications of the chemical analysis of the D2 group of corynebacteria.
PubMed:The rapid diagnosis of tuberculosis: a selective review.
PubMed:Measurement of tuberculostearic acid in sputa, pleural effusions, and bronchial washings. A clinical evaluation for diagnosis of pulmonary tuberculosis.
PubMed:Rapid diagnosis of tuberculous meningitis by frequency-pulsed electron-capture gas-liquid chromatography detection of carboxylic acids in cerebrospinal fluid.
PubMed:Ornithine lipid of Mycobacterium tuberculosis: its distribution in some slow- and fast-growing mycobacteria.
PubMed:[Basic and clinical evaluation of rapid diagnosis of tuberculosis by detecting tuberculostearic acid].
PubMed:The rapid and sensitive diagnosis of tuberculous meningitis by the detection of tuberculostearic acid in cerebrospinal fluid using gas chromatography-mass spectrometry with selective ion monitoring.
PubMed:Gas chromatography of mycobacterial fatty acids and alcohols: diagnostic applications.
PubMed:A tuberculostearic acid assay in the diagnosis of sputum smear-negative pulmonary tuberculosis. A prospective study of bronchoscopic aspirate and lavage specimens.
PubMed:Two-dimensional gas chromatography with electron capture detection for the sensitive determination of specific mycobacterial lipid constituents.
PubMed:[Gas chromatography-mass spectroscopy detection of tuberculostearic acid in the cerebrospinal fluid as a diagnostic aid in the differential diagnosis of tuberculoid meningitis].
PubMed:Isolation and structural characterization of a new non-phosphorylated lipoamino acid from Mycobacterium phlei.
PubMed:Diagnosis of nasopharyngeal tuberculosis by detection of tuberculostearic acid in formalin fixed, paraffin wax embedded tissue biopsy specimens.
PubMed:Characterization of distinct layers of the Mycobacterium avium envelope in respect of their composition by fatty acids, proteins, oligosaccharides and antigens.
PubMed:[Rapid diagnosis of pulmonary tuberculosis by detection of tuberculostearic acid with gas chromatography/mass spectrometry].
PubMed:Tuberculostearic acid in lymph nodes from patients with sarcoidosis.
PubMed:Diagnosis of pulmonary tuberculosis by detection of tuberculostearic acid in sputum by using gas chromatography-mass spectrometry with selected ion monitoring.
PubMed:Diagnosis of tuberculous meningitis by detection of tuberculostearic acid in cerebrospinal fluid.
PubMed:[Role of Tween-80 used in the culture of cutaneous corynebacteria (JK group) on the composition of cellular fatty acids].
PubMed:Disposable reversed-phase chromatography columns for improved detection of carboxylic acids in body fluids by electron-capture gas-liquid chromatography.
PubMed:Selective procedures for detecting femtomole quantities of tuberculostearic acid in serum and cerebrospinal fluid by frequency-pulsed electron capture gas-liquid chromatography.
PubMed:Diagnosis of pulmonary tuberculosis by selected-ion monitoring: improved analysis of tuberculostearate in sputum using negative-ion mass spectrometry.
PubMed:Biochemical characteristics and fatty acid compositions of some armadillo-derived mycobacteria and their relation to Mycobacterium gordonae.
PubMed:Detection of metabolites by frequency-pulsed electron capture gas-liquid chromatography in serum and cerebrospinal fluid of a patient with Nocardia infection.
PubMed:Fatty acid composition and mycolic acid pattern of some chromogenic mycobacteria.
PubMed:Analysis of cellular fatty acids by gas chromatography as a tool in the identification of medically important coryneform bacteria.
PubMed:[Pulmonary tuberculosis with negative sputum smear. Approaches and perspectives].
PubMed:Description of Corynebacterium tuberculostearicum sp. nov., a leprosy-derived Corynebacterium.
PubMed:Nocardia in soils of southeastern Spain: abundance, distribution, and chemical characterisation.
PubMed:A gas-liquid and thin-layer chromatographic study of Mycobacterium fortuitum.
PubMed:Advances in the diagnosis of tuberculosis.
PubMed:Tuberculostearic acid as a diagnostic marker in tuberculous meningitis.
PubMed:Determination of fatty acids and carbohydrate monomers in micro-organisms by means of glass capillary gas chromatography: analysis of Mycobacterium gordonae and Mycobacterium scrofulaceum.
PubMed:Gaschromatography of constitutive fatty acids in Mycobacterium leprae.
PubMed:Lipids in the classification of Nocardioides: reclassification of Arthrobacter simplex (Jensen) lochhead in the genus Nocardioides (Prauser) emend. O'Donnell et al. as Nocardioides simplex comb. nov.
PubMed:Use of selected ion monitoring for detection of tuberculostearic and C32 mycocerosic acid in mycobacteria and in five-day-old cultures of sputum specimens from patients with pulmonary tuberculosis.
PubMed:[Studies on the lipids of "Mycobacterium gordonae" in comparison with those of "M. leprae" and of some other scotochromogenic mycobacteria (author's transl)].
PubMed:Detection of tuberculostearic acid in biological specimens by means of glass capillary gas chromatography-electron and chemical ionization mass spectrometry, utilizing selected ion monitoring.
PubMed:Detection of tuberculostearic acid in mycobacteria and nocardiae by gas chromatography and mass spectrometry using selected ion monitoring.
PubMed:Demonstration of tuberculostearic acid in sputum from patients with pulmonary tuberculosis by selected ion monitoring.
PubMed:Alterations in lipid constituents during growth of Mycobacterium smegmatis CDC 46 and Mycobacterium phlei ATCC 354.
PubMed:Chemical composition of the cell wall of the H37Ra strain of Mycobacterium tuberculosis.
PubMed:Enzymatic synthesis of 10-methylene stearic acid and tuberculostearic acid.
PubMed:The synthesis of tuberculostearic acid.
 
Notes:
characteristic constituent of microorganisms of actinomycetales. Tuberculostearic acid is the characteristic fatty acid of acid-fast bacteria of the order Actinomycetales. (PMID 3329256) Tuberculostearic acid (TBSA) is a mycobacterial cell wall constituent that is possible to measure in plasma samples of patients with active tuberculosis. (PMID 14723350) Detection of tuberculostearic acid in cerebrospinal fluid by use of gas chromatography-mass spectrometry has proven to be a very rapid, sensitive, and specific test for tuberculous meningitis. (PMID 8438134) [HMDB]
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