laevo-lactaldehyde
propanal, 2-hydroxy- (9CI)
 
Notes:
L-lactaldehyde is an intermediate metabolite in the pyruvate metabolism pathway. L-lactaldehyde is irreversibly produced from pyruvaldehyde via the enzyme aldehyde reductase (EC:1.1.1.21) which is then irreversibly converted to propylene glycol via aldehyde reductase (EC:1.1.1.21). [HMDB]
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CAS Number: 598-35-6Picture of molecule3D/inchi
Other(deleted CASRN): 3913-65-3
FDA UNII: S468FB0QE4
Nikkaji Web: J2.715D
Beilstein Number: 1719827
MDL: MFCD21662062
XlogP3-AA: -0.50 (est)
Molecular Weight: 74.07922000
Formula: C3 H6 O2
NMR Predictor: Predict (works with chrome or firefox)
Category: information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Appearance: colorless to pale yellow clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 121.00 to  122.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 6.820000 mmHg @ 25.00 °C. (est)
Flash Point: 98.00 °F. TCC ( 36.80 °C. ) (est)
logP (o/w): -1.250 (est)
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Sigma-Aldrich: Sigma
For experimental / research use only.
DL-Lactaldehyde solution ∼1 M in H2O
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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
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Safety in Use Information:
Category: information only not used for fragrances or flavors
Recommendation for laevo-lactaldehyde usage levels up to:
 not for fragrance use.
 
Recommendation for laevo-lactaldehyde flavor usage levels up to:
 not for flavor use.
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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 : 855
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 2-hydroxypropanal
Chemidplus: 0000598356
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References:
 2-hydroxypropanal
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 855
Pubchem (sid): 135107214
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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): C00424
HMDB (The Human Metabolome Database): HMDB03052
FooDB: FDB023101
YMDB (Yeast Metabolome Database): YMDB00167
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
2-hydroxypropanal
2-hydroxypropionaldehyde
a-hydroxypropionaldehyde
L-lactaldehyde
 lactaldehyde (6CI,7CI,8CI)
 propan-3-one, 2-hydroxy-
 propanal, 2-hydroxy
 propanal, 2-hydroxy-
 propanal, 2-hydroxy- (9CI)
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Articles:
PubMed: Comparative genomics and functional analysis of rhamnose catabolic pathways and regulons in bacteria.
PubMed: Structural and functional analysis of fucose-processing enzymes from Streptococcus pneumoniae.
PubMed: Crystal structure analysis of L-fuculose-1-phosphate aldolase from Thermus thermophilus HB8 and its catalytic action: as explained through in silico.
PubMed: Improving Escherichia coli FucO for furfural tolerance by saturation mutagenesis of individual amino acid positions.
PubMed: Macro-to-micro structural proteomics: native source proteins for high-throughput crystallization.
PubMed: Gas-phase oxidation of methyl crotonate and ethyl crotonate. kinetic study of their reactions toward OH radicals and Cl atoms.
PubMed: Differential inhibition/inactivation of mitochondrial complex I implicates its alteration in malignant cells.
PubMed: Increased furfural tolerance due to overexpression of NADH-dependent oxidoreductase FucO in Escherichia coli strains engineered for the production of ethanol and lactate.
PubMed: Broadening deoxysugar glycodiversity: natural and engineered transaldolases unlock a complementary substrate space.
PubMed: Identification of glycolaldehyde as the key inhibitor of bioethanol fermentation by yeast and genome-wide analysis of its toxicity.
PubMed: Stimulation of reductive glycerol metabolism by overexpression of an aldehyde dehydrogenase in a recombinant Klebsiella pneumoniae strain defective in the oxidative pathway.
PubMed: Effect of aeration strategy on the metabolic flux of Klebsiella pneumoniae producing 1,3-propanediol in continuous cultures at different glycerol concentrations.
PubMed: Requirement of purine and pyrimidine synthesis for colonization of the mouse intestine by Escherichia coli.
PubMed: Expression of 1,3-propanediol oxidoreductase and its isoenzyme in Klebsiella pneumoniae for bioconversion of glycerol into 1,3-propanediol.
PubMed: D-fructose-6-phosphate aldolase in organic synthesis: cascade chemical-enzymatic preparation of sugar-related polyhydroxylated compounds.
PubMed: Stereoselective synthesis of (-)-spicigerolide.
PubMed: Novel modified version of nonphosphorylated sugar metabolism--an alternative L-rhamnose pathway of Sphingomonas sp.
PubMed: A comparative study of methylglyoxal metabolism in trypanosomatids.
PubMed: Sugars, alkaloids, and heteroaromatics: exploring heterocyclic chemistry with alkoxyallenes.
PubMed: Rhamnose catabolism in Bacteroides thetaiotaomicron is controlled by the positive transcriptional regulator RhaR.
PubMed: Metabolic fate of L-lactaldehyde derived from an alternative L-rhamnose pathway.
PubMed: Eukaryotic and bacterial gene clusters related to an alternative pathway of nonphosphorylated L-rhamnose metabolism.
PubMed: Formation of furan and methylfuran by maillard-type reactions in model systems and food.
PubMed: Biochemical origins of lactaldehyde and hydroxyacetone in Methanocaldococcus jannaschii.
PubMed: Enhancement of coenzyme binding by a single point mutation at the coenzyme binding domain of E. coli lactaldehyde dehydrogenase.
PubMed: Role of GldA in dihydroxyacetone and methylglyoxal metabolism of Escherichia coli K12.
PubMed: Total syntheses of carbohydrates: organocatalyzed aldol additions of dihydroxyacetone.
PubMed: Structure of an amide bond forming F(420):gamma-glutamyl ligase from Archaeoglobus fulgidus -- a member of a new family of non-ribosomal peptide synthases.
PubMed: Crystal structure of lactaldehyde dehydrogenase from Escherichia coli and inferences regarding substrate and cofactor specificity.
PubMed: Characterization of E. coli tetrameric aldehyde dehydrogenases with atypical properties compared to other aldehyde dehydrogenases.
PubMed: Identification of lactaldehyde dehydrogenase in Methanocaldococcus jannaschii and its involvement in production of lactate for F420 biosynthesis.
PubMed: Purification, crystallization and preliminary X-ray crystallographic study of the L-fuculose-1-phosphate aldolase (FucA) from Thermus thermophilus HB8.
PubMed: Characterizing NAD-dependent alcohol dehydrogenase enzymes of Methylobacterium extorquens and strawberry (Fragaria x ananassa cv. Elsanta).
PubMed: Krebs cycle anions in metabolic acidosis.
PubMed: NTP-CERHR Monograph on the Potential Human Reproductive and Developmental Effects of Propylene Glycol (PG).
PubMed: Crystal structure of an iron-dependent group III dehydrogenase that interconverts L-lactaldehyde and L-1,2-propanediol in Escherichia coli.
PubMed: Lack of influence of the anaerobic [NiFe] hydrogenase and L-1,2 propanediol oxidoreductase on the outcome of Actinobacillus pleuropneumoniae serotype 7 infection.
PubMed: A synthesis of L-vancosamine derivatives from non-carbohydrate precursors by a short sequence based on the Marshall, McDonald, and Du Bois reactions.
PubMed: Structure and catalytic mechanism of L-rhamnulose-1-phosphate aldolase.
PubMed: Glycolaldehyde induces apoptosis in a human breast cancer cell line.
PubMed: Associating protein activities with their genes: rapid identification of a gene encoding a methylglyoxal reductase in the yeast Saccharomyces cerevisiae.
PubMed: The screening of extracts from Goniothalamus scortechinii, Aralidium pinnatifidum and Andrographis paniculata for anti-malarial activity using the lactate dehydrogenase assay.
PubMed: Catalyst-controlled diastereoselective hetero-Diels-Alder reactions.
PubMed: The structure of L-rhamnulose-1-phosphate aldolase (class II) solved by low-resolution SIR phasing and 20-fold NCS averaging.
PubMed: Total Synthesis of the Cytotoxic Threo, Trans, Erythro, Cis, Threo Annonaceous Acetogenin Trilobin.
PubMed: Studies on the synthesis of landomycin A: synthesis and glycosidation reactions of L-rhodinosyl acetate derivatives.
PubMed: Microbial formation, biotechnological production and applications of 1,2-propanediol.
PubMed: Kinetic, dynamic, and pathway studies of glycerol metabolism by Klebsiella pneumoniae in anaerobic continuous culture: III. Enzymes and fluxes of glycerol dissimilation and 1,3-propanediol formation.
PubMed: Metabolic engineering of a 1,2-propanediol pathway in Escherichia coli.
PubMed: N2,7-bis(1-hydroxy-2-oxopropyl)-2'-deoxyguanosine: identical noncyclic adducts with 1,3-dichloropropene epoxides and methylglyoxal.
PubMed: Site-directed mutagenesis studies of the metal-binding center of the iron-dependent propanediol oxidoreductase from Escherichia coli.
PubMed: 1,3-Dichloropropene epoxides: intermediates in bioactivation of the promutagen 1,3-dichloropropene.
PubMed: Evolution of an Escherichia coli protein with increased resistance to oxidative stress.
PubMed: Construction and characterization of a 1,3-propanediol operon.
PubMed: Similar nature of inhibition of mitochondrial respiration of heart tissue and malignant cells by methylglyoxal. A vital clue to understand the biochemical basis of malignancy.
PubMed: Selective inhibition of mitochondrial respiration and glycolysis in human leukaemic leucocytes by methylglyoxal.
PubMed: Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to convert hydroxy-amino acids into glycolaldehyde, 2-hydroxypropanal, and acrolein. A mechanism for the generation of highly reactive alpha-hydroxy and alpha,beta-unsaturated aldehydes by phagocytes at sites of inflammation.
PubMed: Interaction of aldehydes with glyoxalase I and the status of several aldehyde metabolizing enzymes of Ehrlich ascites carcinoma cells.
PubMed: Catalytic mechanism of the metal-dependent fuculose aldolase from Escherichia coli as derived from the structure.
PubMed: Strain-dependent variation in the NADH-dependent diacetyl reductase activities of larger- and alebrewing yeasts.
PubMed: Inhibition of electron flow through complex I of the mitochondrial respiratory chain of Ehrlich ascites carcinoma cells by methylglyoxal.
PubMed: Purification and characterization of dimeric dihydrodiol dehydrogenase from dog liver.
PubMed: Methylglyoxal, glyoxalases and the development of diabetic complications.
PubMed: Reduction of trioses by NADPH-dependent aldo-keto reductases. Aldose reductase, methylglyoxal, and diabetic complications.
PubMed: Inactivation of propanediol oxidoreductase of Escherichia coli by metal-catalyzed oxidation.
PubMed: Aldehyde dehydrogenase induction by glutamate in Escherichia coli. Role of 2-oxoglutarate.
PubMed: L-lyxose metabolism employs the L-rhamnose pathway in mutant cells of Escherichia coli adapted to grow on L-lyxose.
PubMed: Inhibition of respiration of tumor cells by methylglyoxal and protection of inhibition by lactaldehyde.
PubMed: Effect of epinephrine on ethanol metabolism by isolated rat hepatocytes.
PubMed: Oxygen regulation of L-1,2-propanediol oxidoreductase activity in Escherichia coli.
PubMed: Hydrogen peroxide mediates the oxidative inactivation of enzymes following the switch from anaerobic to aerobic metabolism in Klebsiella pneumoniae.
PubMed: Non-culture tests for the diagnosis of gonorrhea.
PubMed: Sexual response in Saccharomyces cerevisiae: alteration of enzyme activity in the glyoxalase system by mating factor.
PubMed: [Diagnosis of gonorrhea using a microfluorimetric Neisseria gonorrheae-specific enzyme detection test].
PubMed: Similarity of Escherichia coli propanediol oxidoreductase (fucO product) and an unusual alcohol dehydrogenase from Zymomonas mobilis and Saccharomyces cerevisiae.
PubMed: Methylglyoxal-catabolizing enzymes of Leishmania donovani promastigotes.
PubMed: Anaerobic growth of Escherichia coli on glycerol by importing genes of the dha regulon from Klebsiella pneumoniae.
PubMed: 2-Oxoaldehyde metabolism in microorganisms.
PubMed: L-1,2-propanediol exits more rapidly than L-lactaldehyde from Escherichia coli.
PubMed: Aerobic excretion of 1,2-propanediol by Salmonella typhimurium.
PubMed: A mutant crp allele that differentially activates the operons of the fuc regulon in Escherichia coli.
PubMed: Kinetics of propylene glycol elimination and metabolism in rat.
PubMed: Metabolism of 2-oxoaldehyde in mold. Purification and characterization of two methylglyoxal reductases from Aspergillus niger.
PubMed: Metabolism of L-fucose and L-rhamnose in Escherichia coli: aerobic-anaerobic regulation of L-lactaldehyde dissimilation.
PubMed: Involvement of lactaldehyde dehydrogenase in several metabolic pathways of Escherichia coli K12.
PubMed: Cross-induction of the L-fucose system by L-rhamnose in Escherichia coli.
PubMed: NAD-linked aldehyde dehydrogenase for aerobic utilization of L-fucose and L-rhamnose by Escherichia coli.
PubMed: Loss of aldehyde dehydrogenase in an Escherichia coli mutant selected for growth on the rare sugar L-galactose.
PubMed: Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae.
PubMed: Propanediol oxidoreductases of Escherichia coli, Klebsiella pneumoniae and Salmonella typhimurium. Aspects of interspecies structural and regulatory differentiation.
PubMed: Metabolism of 2-oxoaldehyde in yeasts. Purification and characterization of NADPH-dependent methylglyoxal-reducing enzyme from Saccharomyces cerevisiae.
PubMed: Identity of Escherichia coli D-1-amino-2-propanol:NAD+ oxidoreductase with E. coli glycerol dehydrogenase but not with Neisseria gonorrhoeae 1,2-propanediol:NAD+ oxidoreductase.
PubMed: Fermentation mechanism of fucose and rhamnose in Salmonella typhimurium and Klebsiella pneumoniae.
PubMed: Oxidation of lactaldehyde by cytosolic aldehyde dehydrogenase and inhibition of cytosolic and mitochondrial aldehyde dehydrogenase by metabolites.
PubMed: Purification and partial characterization of a methylglyoxal reductase from goat liver.
PubMed: Constitutive activation of L-fucose genes by an unlinked mutation in Escherichia coli.
PubMed: L-Rhamnose utilisation in Salmonella typhimurium.
PubMed: Genetic and structural evidence for the presence of propanediol oxidoreductase isoenzymes in Escherichia coli.
PubMed: Dual control of a common L-1,2-propanediol oxidoreductase by L-fucose and L-rhamnose in Escherichia coli.
PubMed: Fermentation of 6-Deoxyhexoses by Bacillus macerans.
PubMed: The metabolism of acetone in rat.
PubMed: Post-transcriptional control of L-1,2-propanediol oxidoreductase in the L-fucose pathway of Escherichia coli K-12.
PubMed: Use of operon fusions to examine the regulation of the L-1,2-propanediol oxidoreductase gene of the fucose system in Escherichia coli K12.
PubMed: Identification of lactaldehyde dehydrogenase and glycolaldehyde dehydrogenase as functions of the same protein in Escherichia coli.
PubMed: Experimental evolution of a metabolic pathway for ethylene glycol utilization by Escherichia coli.
PubMed: Detection of Neisseria gonorrhoeae by ultraviolet illumination of NADH generated by an immobilized antibody-gonococcal enzyme complex.
PubMed: Chemical trapping of labile aldehyde intermediates in the metabolism of propranolol and oxprenolol.
PubMed: Metabolism of L-fucose and L-rhamnose in Escherichia coli: differences in induction of propanediol oxidoreductase.
PubMed: Methylgloxal: enzyme distributions relative to its presence in Douglas-fir needles and absence in Douglas-fir needle callus.
PubMed: Experimental evolution of propanediol oxidoreductase in Escherichia coli. Comparative analysis of the wild-type and mutant enzymes.
PubMed: Enzymatic detection of Neisseria gonorrhoeae.
PubMed: Bacterial metabolism of propane-1,2-diol.
PubMed: Rhamnose-induced propanediol oxidoreductase in Escherichia coli: purification, properties, and comparison with the fucose-induced enzyme.
PubMed: Periodate oxidation analysis of carbohydrates. XIII. Simultaneous gas chromatographic determination of the aldehydes in the periodate oxidation products of non-dialyzable urinary carbohydrate materials as diethyl dithioacetals.
PubMed: Xylose, arabinose, and rhamnose fermentation by Bacteroides ruminicola.
PubMed: Evolution of propanediol utilization in Escherichia coli: mutant with improved substrate-scavenging power.
PubMed: Regulatory changes in the fucose system associated with the evolution of a catabolic pathway for propanediol in Escherichia coli.
PubMed: Assay of brain and liver alcohol dehydrogenase by the coupled oxido-reduction of ethanol and lactaldehyde in the presence of deoxycholate.
PubMed: Metabolism of L-rhamnose in Arthrobacter pyridinolis.
PubMed: Disruption of the fucose pathway as a consequence of genetic adaptation to propanediol as a carbon source in Escherichia coli.
PubMed: Evolution of L-1, 2-propanediol catabolism in Escherichia coli by recruitment of enzymes for L-fucose and L-lactate metabolism.
PubMed: D-Fucose metabolism in a pseudomonad. IV. Cleavage of 2-keto-3-deoxy-D-fuconate to pyruvate and D-lactaldehyde by 2-keto-3-deoxy-L-arabonate aldolase.
PubMed: Threonine metabolism in a strain of Bacillus subtilis: enzymic oxidation of the intermediate DL-lactaldehyde.
PubMed: Purification and properties of lactaldehyde dehydrogenase from Escherichia coli.
PubMed: THE METABOLISM OF LACTALDEHYDE. VII. THE OXIDATION OF D-LACTALDEHYDE IN RAT LIVER.
PubMed: THE METABOLISM OF LACTALDEHYDE. VI. THE REDUCTION OF D- AND L-LACTALDEHYDE IN RAT LIVER.
PubMed: The enzymatic conversion of lactaldehyde to propanediol.
PubMed: The metabolism of lactaldehyde. V. Metabolism of L-fucose.
PubMed: Studies on the metabolism of lactaldehyde. IV. The metabolism of D-rhamnulose-1-phosphate and 6-deoxy-L-sorbose-1-phosphate.
PubMed: Studies on the metabolism of lactaldehyde. III. By alcohol and aldehyde dehydrogenase.
PubMed: Studies on the metabolism of lactaldehyde. II. By bakers' yeast cells.
PubMed: Studies on the metabolism of lactaldehyde. I. Separation and determination of lactaldehyde and related 3-carbon compounds.
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