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3-hydroxydodecanoic acid
b-hydroxylauric acid

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Name:3-hydroxydodecanoic acid
CAS Number: 1883-13-2Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J111.042J
MDL:MFCD00133279
XlogP3-AA:3.60 (est)
Molecular Weight:216.32088000
Formula:C12 H24 O3
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
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: 348.00 °C. @ 760.00 mm Hg (est)
Flash Point: 353.00 °F. TCC ( 178.40 °C. ) (est)
logP (o/w): 3.110 (est)
Soluble in:
 water, 321.3 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.
3-Hydroxy lauric acid ≥98%
Odor: characteristic
Use: 3-Hydroxy lauric acid is a hydroxylated fatty acid that is found in bacteria as well as Pseudosuberites and D. calyx sea sponge
Sigma-Aldrich: Sigma
For experimental / research use only.
DL-β-Hydroxylauric acid ≥99% (GC)
sds
 
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:
information only not used for fragrances or flavors
Recommendation for 3-hydroxydodecanoic acid usage levels up to:
 not for fragrance use.
 
Recommendation for 3-hydroxydodecanoic 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 :94216
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
3-hydroxydodecanoic acid
Chemidplus:0001883132
 
References:
 3-hydroxydodecanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):94216
Pubchem (sid):135051921
 
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):HMDB00387
FooDB:FDB022005
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 dodecanoic acid, 3-hydroxy-
b-hydroxylauric acid
beta-hydroxylauric acid
 

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:Analysis of polyhydroxyalkanoate (PHA) synthase gene and PHA-producing bacteria in activated sludge that produces PHA containing 3-hydroxydodecanoate.
PubMed:Production of medium-chain-length 3-hydroxyalkanoic acids by β-oxidation and phaC operon deleted Pseudomonas entomophila harboring thioesterase gene.
PubMed:The Burkholderia cenocepacia BDSF quorum sensing fatty acid is synthesized by a bifunctional crotonase homologue having both dehydratase and thioesterase activities.
PubMed:Functional characterization of an NADPH dependent 2-alkyl-3-ketoalkanoic acid reductase involved in olefin biosynthesis in Stenotrophomonas maltophilia.
PubMed:Role of pagL and lpxO in Bordetella bronchiseptica lipid A biosynthesis.
PubMed:Disturbance of mitochondrial energy homeostasis caused by the metabolites accumulating in LCHAD and MTP deficiencies in rat brain.
PubMed:Structural basis for the sugar nucleotide and acyl-chain selectivity of Leptospira interrogans LpxA.
PubMed:Microbial production of 3-hydroxydodecanoic acid by pha operon and fadBA knockout mutant of Pseudomonas putida KT2442 harboring tesB gene.
PubMed:Up-cycling of PET (polyethylene terephthalate) to the biodegradable plastic PHA (polyhydroxyalkanoate).
PubMed:Pseudomonas japonica sp. nov., a novel species that assimilates straight chain alkylphenols.
PubMed:Production of polyhydroxyalkanoates with high 3-hydroxydodecanoate monomer content by fadB and fadA knockout mutant of Pseudomonas putida KT2442.
PubMed:The evaluation of the role of beta-hydroxy fatty acids on chronic inflammation and insulin resistance.
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:Pseudomonas lutea sp. nov., a novel phosphate-solubilizing bacterium isolated from the rhizosphere of grasses.
PubMed:Pseudomonas rhizosphaerae sp. nov., a novel species that actively solubilizes phosphate in vitro.
PubMed:Structural determination of lipid A of the lipopolysaccharide from Pseudomonas reactans. A pathogen of cultivated mushrooms.
PubMed:Analysis of 3-hydroxydodecanedioic acid for studies of fatty acid metabolic disorders: preparation of stable isotope standards.
PubMed:Production of chiral R-3-hydroxyalkanoic acids and R-3-hydroxyalkanoic acid methylesters via hydrolytic degradation of polyhydroxyalkanoate synthesized by pseudomonads.
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:A new extraction method for Acinetobacter species ODB-L2 rough form lipopolysaccharide from culture broth.
PubMed:Absolute configuration of aflastatin A, a specific inhibitor of aflatoxin production by Aspergillus parasiticus.
PubMed:Production of polyhydroxyalkanoic acids by Ralstonia eutropha and Pseudomonas oleovorans from an oil remaining from biotechnological rhamnose production.
PubMed:Outer membrane changes in a toluene-sensitive mutant of toluene-tolerant Pseudomonas putida IH-2000.
PubMed:A taxonomic study of bacteria isolated from grasses: a proposed new species Pseudomonas graminis sp. nov.
PubMed:Incorporation of 2-hydroxyl fatty acids by Acinetobacter calcoaceticus RAG-1 to tailor emulsan structure.
PubMed:Arthrichitin. A New Cell Wall Active Metabolite from Arthrinium phaeospermum.
PubMed:General strategy for structural analysis of the oligosaccharide region of lipooligosaccharides. Structure of the oligosaccharide component of Pseudomonas aeruginosa IATS serotype 06 mutant R5 rough-type lipopolysaccharide.
PubMed:Characterization of the lipopolysaccharide of Moraxella catarrhalis. Structural analysis of the lipid A from M. catarrhalis serotype A lipopolysaccharide.
PubMed:Identification, isolation, and structural studies of the outer membrane lipopolysaccharide of Caulobacter crescentus.
PubMed:Characterization of lipid A from Pseudomonas aeruginosa O-antigenic B band lipopolysaccharide by 1D and 2D NMR and mass spectral analysis.
PubMed:Structural characterization of the lipid A component of pathogenic Neisseria meningitidis.
PubMed:Structural characterization of the lipid A component of Pseudomonas aeruginosa wild-type and rough mutant lipopolysaccharides.
PubMed:Structural studies of lipid A from Pseudomonas aeruginosa PAO1: occurrence of 4-amino-4-deoxyarabinose.
PubMed:The structure of syringomycins A1, E and G.
PubMed:Studies on the antigenic S-type lipopolysaccharides of Brucella abortus strains 7 and Mustapha.
PubMed:Differentiation of Campylobacter and Campylobacter-like organisms by cellular fatty acid composition.
PubMed:Biosynthesis of 3-hydroxy fatty acids, the pheromone components of female mallard ducks, by cell-free preparations from the uropygial gland.
PubMed:Structural studies on the core oligosaccharide of Phenylobacterium immobile strain K2 lipopolysaccharide. Chemical synthesis of 3-hydroxy-5c-dodecenoic acid.
PubMed:The lipopolysaccharide of a chloridazon-degrading bacterium.
PubMed:Lipopolysaccharides from Pseudomonas maltophilia. Structural studies of the side-chain, core, and lipid-A regions of the lipopolysaccharide from strain NCTC 10257.
PubMed:Characteristic lipids of Bordetella pertussis: simple fatty acid composition, hydroxy fatty acids, and an ornithine-containing lipid.
PubMed:Isolation of a relatively pure outer membrane fraction of Moraxella nonliquefaciens and a comparison of its characteristics with the cytoplasmic membrane-containing material.
PubMed:Lipids and fatty acids of a moderately halophilic bacterium, No. 101.
PubMed:The purification and chemical composition of the lipopolysaccharide of Pseudomonas alcaligenes.
PubMed:The chemical composition of the lipopolyacarideof Pseudomonas aeruginosa.
 
Notes:
3-Hydroxydodecanoic acid is a medium-chain fatty acid associated with fatty acid metabolic disorders (PMID 11948802). Deficiency of medium-chain acyl-CoA dehydrogenase is characterized by intolerance to prolonged fasting, recurrent episodes of hypoglycemic coma with medium-chain dicarboxylic aciduria, impaired ketogenesis, and low plasma and tissue carnitine levels. (OMIM 201450) [HMDB]
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