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laevo-malic acid
L-malic acid

Supplier Sponsors

Name:(2S)-2-hydroxybutanedioic acid
CAS Number: 97-67-6Picture of molecule3D/inchi
Other(deleted CASRN):124501-05-9
ECHA EINECS - REACH Pre-Reg:202-601-5
Nikkaji Web:J74.430A
Beilstein Number:1723541
CoE Number:17
XlogP3:-1.30 (est)
Molecular Weight:134.08782000
Formula:C4 H6 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
EFSA/JECFA Comments:
JECFA evaluated l-malic acid (CASrn 97-67-6). (R)- or (S)- enantiomer not specified by CASrn in Register. GrADI: not specified (JECFA, 1970a).
Category:flavoring agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Perfumer and Flavorist:Search
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Pubchem Patents:Search
 FDA/DG SANTE Petitions, Reviews, Notices:
184.1069 L-malic acid View - review
184.1069 malic acid View - review
EU SANCO Malic acid View - review
JECFA Food Flavoring:619 L-malic acid
FEMA Number:2655 L-malic acid
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):97-67-6 ; L-MALIC ACID
FDA Regulation:
Subpart B--Requirements for Specific Standardized Fruit Butters, Jellies, Preserves, and Related Products
Sec. 150.141 Artificially sweetened fruit jelly.

Subpart B--Requirements for Specific Standardized Fruit Butters, Jellies, Preserves, and Related Products
Sec. 150.161 Artificially sweetened fruit preserves and jams.

Subpart B--Requirements for Specific Standardized Food Dressings and Flavorings
Sec. 169.115 French dressing.

Subpart B--Requirements for Specific Standardized Food Dressings and Flavorings
Sec. 169.140 Mayonnaise.

Subpart B--Requirements for Specific Standardized Food Dressings and Flavorings
Sec. 169.150 Salad dressing.

Subpart B--Listing of Specific Substances Affirmed as GRAS
Sec. 184.1069 Malic acid.
Physical Properties:
Assay: 96.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:1.59500 @ 20.00 °C.
Melting Point: 99.00 to 100.00 °C. @ 760.00 mm Hg
Boiling Point: 140.00 °C. @ 760.00 mm Hg
Flash Point: 308.00 °F. TCC ( 153.33 °C. )
logP (o/w): -1.370 (est)
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor Strength:none
Odor Description:at 100.00 %. odorless
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: buffering agents
BOC Sciences
For experimental / research use only.
L(-)-Malic Acid >98.0%(GC)(T)
Covalent Chemical
L-Malic Acid
ECSA Chemicals
Foodchem International
L-Malic Acid
Glentham Life Sciences
L-(-)-Malic acid
Jiangyin Healthway
L-Malic Acid
New functional food ingredients
Maypro Industries
L-Malic Acid
Penta International
Penta International
Penta International
Penta International
Penta International
Qingdao Dacon Trading
L(-)-Malic Acid
Santa Cruz Biotechnology
For experimental / research use only.
L-(-)-Malic Acid ≥99%
For experimental / research use only.
L-(-)-Malic Acid ReagentPlus®, ≥99%
For experimental / research use only.
L-(-)-Malic Acid >98.0%(T)
Tianjin Talent Chemical
Malic Acid (DL / L)
Vevy Europe
Odor: characteristic
Use: it favourably modify the moisture content and elasticity of the skin. Because of its slight exfoliation effect deriving from the natural intrinsic properties of malic acid, it is also useful for cosmetic products designed to improve the appearance and softness of the skin as well as to prevent formation of small wrinkles.
Zhong Ya Chemical
L-Malic Acid
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 22 - Do not breath dust.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
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
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50 1600 mg/kg

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
flavoring agents
Recommendation for laevo-malic acid usage levels up to:
 not for fragrance use.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3. Update in publication number(s): 29
Click here to view publication 3
 average usual ppmaverage maximum ppm
baked goods: 0.600002.00000
beverages(nonalcoholic): 90.00000380.00000
beverages(alcoholic): 1200.0000010000.00000
breakfast cereal: --
cheese: --
chewing gum: 6000.0000025000.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 25.00000390.00000
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 420.00000420.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 25.00000420.00000
soups: --
sugar substitutes: --
sweet sauces: --
Safety References:
European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Flavouring Group Evaluation 29 (FGE29)[1] - Substance from the priority list: Vinylbenzene from chemical group 31 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab)
View page or View pdf

Scientific Report of EFSA on the risk assessment of salts of authorised acids, phenols or alcohols for use in food contact materials [1]
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 92 (FGE.92): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (68th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones evaluated by EFSA in FGE.10Rev1 (2009)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 10, Revision 2 (FGE.10Rev2): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):97-67-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :222656
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S)-2-hydroxybutanedioic acid
 (2S)-2-hydroxybutanedioic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:97-67-6
Pubchem (cid):222656
Pubchem (sid):135017855
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
FDA Substances Added to Food (formerly EAFUS):View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C00149
HMDB (The Human Metabolome Database):HMDB00156
YMDB (Yeast Metabolome Database):YMDB00280
Export Tariff Code:2918.19.6000
FDA Listing of Food Additive Status:View
VCF-Online:VCF Volatile Compounds in Food
FAO:(-)-Malic acid
•uva ursi, this is volatile oil containing a glucoside, arbutin, tannin, & gallic & malic acids. •grades: technical, active and inactive; fcc. the natural material is levorotatory, but the synthetic material is optically inactive •food grade: powder, fine granular, and granular •granules and powder grades
Potential Blenders and core components note
None Found
Potential Uses:
 buffering agents
Occurrence (nature, food, other):note
 apple fruit
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 apple plant
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 guava fruit
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 maple sap
Search PMC Picture
 peach fruit
Search Trop Picture
 pineapple fruit
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 pomegranate fruit
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 apple acid
L-apple acid
 butanedioic acid, 2-hydroxy-, (2S)-
 butanedioic acid, hydroxy-, (2S)-
 butanedioic acid, hydroxy-, (S)-
(S)-(-)-hydrosuccinic acid
(S)-hydroxy-butanedioic acid
(2S)-2-hydroxybutane dioic acid
2-hydroxybutane dioic acid
S-2-hydroxybutane dioic acid
(2S)-2-hydroxybutanedioic acid
(S)-hydroxybutanedioic acid
L-hydroxybutanedioic acid
S-2-hydroxybutanedioic acid
(-)-hydroxysuccinic acid
(2S)-2-hydroxysuccinic acid
(S)-(-)-hydroxysuccinic acid
(S)-(-)-2-hydroxysuccinic acid
(S)-2-hydroxysuccinic acid
L-hydroxysuccinic acid
 keresine (Vevy)
(-)-malic acid
(-)-(S)-malic acid
(-)-L-malic acid
(S)-malic acid
(S)-(-)-malic acid
L-malic acid
L-(-)-malic acid
laevo-(-)-malic acid
S-(-)-malic acid
L-malic acid NF
 malic acid, L-


PubMed:Effects of L-Malic Acid on Alpha-Glucosidase: Inhibition Kinetics and Computational Molecular Dynamics Simulations.
PubMed:Enhanced deacidification activity in Schizosaccharomyces pombe by genome shuffling.
PubMed:Efficient synthesis of kinsenoside and goodyeroside a by a chemo-enzymatic approach.
PubMed:Bioconversion of Fumaric Acid to L-malic Acid by the Bacteria of the Genus Nocardia.
PubMed:A mathematical model of the link between growth and L-malic acid consumption for five strains of Oenococcus oeni.
PubMed:Taxonomy of Aureobasidium spp. and biosynthesis and regulation of their extracellular polymers.
PubMed:Implications of new research and technologies for malolactic fermentation in wine.
PubMed:Microbial biosynthesis and secretion of l-malic acid and its applications.
PubMed:A spectrophotometric procedure for malic acid determination in wines employing a multicommutation approach.
PubMed:Selection and characterization of a Patagonian Pichia kudriavzevii for wine deacidification.
PubMed:Multilayer films assembled from naturally-derived materials for controlled protein release.
PubMed:Glycerol production by Oenococcus oeni during sequential and simultaneous cultures with wine yeast strains.
PubMed:Cofactor and CO2 donor regulation involved in reductive routes for polymalic acid production by Aureobasidium pullulans CCTCC M2012223.
PubMed:Process characterization and influence of alternative carbon sources and carbon-to-nitrogen ratio on organic acid production by Aspergillus oryzae DSM1863.
PubMed:Sequential inoculation versus co-inoculation in Cabernet Franc wine fermentation.
PubMed:[Construction and fermentation control of reductive TCA pathway for malic acid production in Saccharomyces cerevisiae].
PubMed:Preparation and pH controlled release of polyelectrolyte complex of poly(L-malic acid-co-D,L-lactic acid) and chitosan.
PubMed:Effect of acclimation medium on cell viability, membrane integrity and ability to consume malic acid in synthetic wine by oenological Lactobacillus plantarum strains.
PubMed:Chemical guide parameters for Punica granatum cv. 'Mollar' fruit juices processed at industrial scale.
PubMed:Diastereoselective synthesis of the C14–C29 fragment of amphidinol.
PubMed:Toxicity and efficacy evaluation of multiple targeted polymalic acid conjugates for triple-negative breast cancer treatment.
PubMed:Design and exploratory data analysis of a second generation of dendrimer prodrugs potentially antichagasic and leishmanicide.
PubMed:[Anticancer activity of oxovanadium compounds].
PubMed:A new strategy for the synthesis of crucigasterin A, and cytotoxic activity of this compound and its related analogues.
PubMed:Metabolic engineering of Aspergillus oryzae NRRL 3488 for increased production of L-malic acid.
PubMed:On-line capillary electrophoresis enrichment by combining chitosan trapping with surfactant assisted sample stacking for the ultratrace determination of organic acids in Plateau alfalfa roots.
PubMed:High-level production of calcium malate from glucose by Penicillium sclerotiorum K302.
PubMed:The cardioprotective effects of citric Acid and L-malic Acid on myocardial ischemia/reperfusion injury.
PubMed:Arsenic mobilization by citrate and malate from a red mud-treated contaminated soil.
PubMed:Patagonian red wines: selection of Lactobacillus plantarum isolates as potential starter cultures for malolactic fermentation.
PubMed:Effect of metformin on the urinary metabolites of diet-induced-obese mice studied by ultra performance liquid chromatography coupled to time-of-flight mass spectrometry (UPLC-TOF/MS).
PubMed:Evaluation of sequential inoculation of Saccharomyces cerevisiae and Oenococcus oeni strains on the chemical and aromatic profiles of cherry wines.
PubMed:Immobilization of malate dehydrogenase on carbon nanotubes for development of malate biosensor.
PubMed:Malolactic enzyme from Oenococcus oeni: heterologous expression in Escherichia coli and biochemical characterization.
PubMed:Cellular Delivery of Doxorubicin via pH-Controlled Hydrazone Linkage Using Multifunctional Nano Vehicle Based on Poly(β-L-Malic Acid).
PubMed:Production of poly(β-L-malic acid) (PMA) from agricultural biomass substrates by Aureobasidium pullulans.
PubMed:Genetic and phenotypic strain heterogeneity within a natural population of Oenococcus oeni from Amarone wine.
PubMed:Modification of Microbial Polymalic Acid With Hydrophobic Amino Acids for Drug-Releasing Nanoparticles.
PubMed:Prevalent lactic acid bacteria in cider cellars and efficiency of Oenococcus oeni strains.
PubMed:[Determination of ionic liquid anions of trifluoroacetate, thiocyanate, tetrafluoroborate and trifluoromethanesulfonate by ion-pair chromatography with direct conductivity detection].
PubMed:Adsorption characteristics of malic acid from aqueous solutions by weakly basic ion-exchange chromatography.
PubMed:A Bacillus subtilis sensor kinase involved in triggering biofilm formation on the roots of tomato plants.
PubMed:Crystal engineering of stable temozolomide cocrystals.
PubMed:Phenotypic and genotypic diversity of wine yeasts used for acidic musts.
PubMed:Synthesis of the macrolactone core of (+)-neopeltolide by transannular cyclization.
PubMed:Heterologous expression of Oenococcus oeni malolactic enzyme in Lactobacillus plantarum for improved malolactic fermentation.
PubMed:Intensification of β-poly(L: -malic acid) production by Aureobasidium pullulans ipe-1 in the late exponential growth phase.
PubMed:Nanobiopolymer for direct targeting and inhibition of EGFR expression in triple negative breast cancer.
PubMed:[Study on the bioleaching mechanism of manganse (II) from manganese-electrolytic residue by manganese-resistant strain Fusarium sp].
PubMed:Molecular modeling study on the disassembly of dendrimers designed as potential antichagasic and antileishmanial prodrugs.
PubMed:VO2+ complexation by bioligands showing keto-enol tautomerism: a potentiometric, spectroscopic, and computational study.
PubMed:Genomic variations of Oenococcus oeni strains and the potential to impact on malolactic fermentation and aroma compounds in wine.
PubMed:Poly(methyl malate) nanoparticles: formation, degradation, and encapsulation of anticancer drugs.
PubMed:Poly(β-L-malic acid) production by diverse phylogenetic clades of Aureobasidium pullulans.
PubMed:High-level production of poly (β-L: -malic acid) with a new isolated Aureobasidium pullulans strain.
PubMed:[Synthesis and hypoglycemic activity of bis(L-malato)oxovanadium(IV)].
PubMed:The optimization of polymalic acid peptide copolymers for endosomolytic drug delivery.
PubMed:Physiological and genetic stability of hybrids of industrial wine yeasts Saccharomyces sensu stricto complex.
PubMed:Production of fumaric acid by Rhizopus oryzae: role of carbon-nitrogen ratio.
PubMed:Sedative, hypnotic and anticonvulsant activities of the ethanol fraction from Rhizoma Pinelliae Praeparatum.
PubMed:Factors influencing the production of volatile phenols by wine lactic acid bacteria.
PubMed:Polymalic acid-based nanobiopolymer provides efficient systemic breast cancer treatment by inhibiting both HER2/neu receptor synthesis and activity.
PubMed:Expression and characterization of fumarase (FUMR) from Rhizopus oryzae.
PubMed:Anti-hyperglycemic activity of chromium(III) malate complex in alloxan-induced diabetic rats.
PubMed:Molecular and biochemical diversity of Oenococcus oeni strains isolated during spontaneous malolactic fermentation of Malvasia Nera wine.
PubMed:The food additives inulin and stevioside counteract oxidative stress.
PubMed:Inhibition of brain tumor growth by intravenous poly (β-L-malic acid) nanobioconjugate with pH-dependent drug release [corrected].
PubMed:Bacillithiol, a new player in bacterial redox homeostasis.
PubMed:Synthesis and organocatalytic ring-opening polymerization of cyclic esters derived from l-malic acid.
PubMed:Alkali production associated with malolactic fermentation by oral streptococci and protection against acid, oxidative, or starvation damage.
PubMed:Temozolomide delivery to tumor cells by a multifunctional nano vehicle based on poly(β-L-malic acid).
PubMed:Biosynthesis and functions of bacillithiol, a major low-molecular-weight thiol in Bacilli.
PubMed:Nanoconjugate Platforms Development Based in Poly(β,L-Malic Acid) Methyl Esters for Tumor Drug Delivery.
PubMed:Impact of the co-culture of Saccharomyces cerevisiae-Oenococcus oeni on malolactic fermentation and partial characterization of a yeast-derived inhibitory peptidic fraction.
PubMed:Requirement of the Lactobacillus casei MaeKR two-component system for L-malic acid utilization via a malic enzyme pathway.
PubMed:New approaches for the synthesis of erythrinan alkaloids.
PubMed:Bacillithiol is an antioxidant thiol produced in Bacilli.
PubMed:Synergistic effect of mediator-carbon nanotube composites for dehydrogenases and peroxidases based biosensors.
PubMed:On the interactions of alkyl 2-hydroxycarboxylic acids with alkoxysilanes 2. Complexation and esterification of di- and tricarboxylic acids.
PubMed:Enhanced docosahexaenoic acid production by reinforcing acetyl-CoA and NADPH supply in Schizochytrium sp. HX-308.
PubMed:Activity of ethanol-stressed Oenococcus oeni cells: a flow cytometric approach.
PubMed:An Ugi reaction in the total synthesis of (-)-dysibetaine.
PubMed:Production of L-malic acid with fixation of HCO3(-) by malic enzyme-catalyzed reaction based on regeneration of coenzyme on electrode modified by layer-by-layer self-assembly method.
PubMed:Antifeedants of Indian barnyard millet, Echinochloa frumentacea link, against brown planthopper, Nilaparvata lugens (Stål).
PubMed:Interaction of l-malic acid with alkaline metals and open chain polyammonium cations in aqueous solution.
PubMed:Root-secreted malic acid recruits beneficial soil bacteria.
PubMed:Cooperative self-assembly of chiral L-malate and achiral succinate in the formation of a three-dimensional homochiral framework.
PubMed:Quantitative reconstruction of the nonvolatile sensometabolome of a red wine.
PubMed:Reverse reaction of malic enzyme for HCO3- fixation into pyruvic acid to synthesize L-malic acid with enzymatic coenzyme regeneration.
PubMed:A chemoenzymatic approach to the synthesis of enantiomerically pure (S)-3-hydroxy-gamma-butyrolactone.
PubMed:A microcalorimetric sensor for food and cosmetic analyses: l-Malic acid determination.
PubMed:Biodegradable nanoparticles of partially methylated fungal poly(beta-L-malic acid) as a novel protein delivery carrier.
PubMed:Synthesis, degradability, and drug releasing properties of methyl esters of fungal poly(beta,L-malic acid).
PubMed:Assimilable nitrogen utilisation and production of volatile and non-volatile compounds in chemically defined medium by Saccharomyces cerevisiae wine yeasts.
PubMed:Characterization of a Lactobacillus plantarum strain able to produce tyramine and partial cloning of a putative tyrosine decarboxylase gene.
PubMed:Brain tumor tandem targeting using a combination of monoclonal antibodies attached to biopoly(beta-L-malic acid).
PubMed:Ionic complexes of biosynthetic poly(malic acid) and poly(glutamic acid) as prospective drug-delivery systems.
PubMed:The infrared dielectric tensor and axial dispersion in caesium L-malate monohydrate.
PubMed:Dual effect of organic acids as a function of external pH in Oenococcus oeni.
PubMed:High-throughput microplate enzymatic assays for fast sugar and acid quantification in apple and tomato.
PubMed:Nanoconjugate based on polymalic acid for tumor targeting.
PubMed:L-(-)-malic acid production by Saccharomyces spp. during the alcoholic fermentation of wine (1).
PubMed:Fluorescent sensing layer for the determination of L-malic acid in wine.
PubMed:Stereoselective synthesis of the glycosidase inhibitor australine through a one-pot, double-cyclization strategy.
PubMed:Thermal decomposition of fungal poly(beta,L-malic acid) and Poly(beta,L-malate)s.
PubMed:Apoptolidinone A: synthesis of the apoptolidin A aglycone.
PubMed:Preparation of insulin nanoparticles and their encapsulation with biodegradable polyelectrolytes via the layer-by-layer adsorption.
PubMed:Brucine salts of L-alpha-hydroxy acids: brucinium hydrogen (S)-malate pentahydrate and anhydrous brucinium hydrogen (2R,3R)-tartrate at 130 K.
PubMed:Polycefin, a new prototype of a multifunctional nanoconjugate based on poly(beta-L-malic acid) for drug delivery.
PubMed:[Study on chemical constituents from Opuntia dillenii].
PubMed:Screening for beta-poly(L-malate) binding proteins by affinity chromatography.
PubMed:Nanostructurated complexes of poly(beta,L-malate) and cationic surfactants: synthesis, characterization and structural aspects.
PubMed:Production of L-malic acid by permeabilized cells of commercial Saccharomyces sp. strains.
PubMed:Stimulation of Erwinia sp. fumarase and aspartase synthesis by changing medium components.
PubMed:Low-molecular-weight poly(alpha-methyl beta,L-malate) of microbial origin: synthesis and crystallization.
PubMed:In situ formation of meso-2,2'-oxydisuccinate via intermolecular dehydration coupling of D,L-malic acid: first coordination polymer of 2,2'-oxydisuccinate involving ether oxygen coordination: [Cd2(meso-odsc)(H2O)].
PubMed:Effect of dipeptides on the growth of Oenococcus oeni in synthetic medium deprived of amino acids.
PubMed:Total synthesis of (+)-brasilenyne. Application of an intramolecular silicon-assisted cross-coupling reaction.
PubMed:New approaches to the industrial synthesis of HIV protease inhibitors.
PubMed:Improved synthesis with high yield and increased molecular weight of poly(alpha,beta-malic acid) by direct polycondensation.
PubMed:Application of conformation design in acyclic stereoselection: total synthesis of borrelidin as the crystalline benzene solvate.
PubMed:Microbial synthesis of the energetic material precursor 1,2,4-butanetriol.
PubMed:Enzymatic browning and biochemical alterations in black spots of pineapple [Ananas comosus (L.) Merr.].
PubMed:Synthesis of (R)-2-methyl-4-deoxy and (R)-2-methyl-4,5-dideoxy analogues of 6-phosphogluconate as potential inhibitors of 6-phosphogluconate dehydrogenase.
PubMed:Transport of glutamate in Oenococcus oeni 8403.
PubMed:Natural phenylpropanoids protect endothelial cells against oxidized LDL-induced cytotoxicity.
PubMed:The structure of the O-specific polysaccharide chain of the Shewanella algae BrY lipopolysaccharide.
PubMed:[Studies on the correlation between production of L-malic acid and some cytosolic enzymes in the L-malic acid producing strain Aspergillus sp. N1-14].
PubMed:Effect of L-malic and citric acids metabolism on the essential amino acid requirements for Oenococcus oeni growth.
PubMed:Conversion of fumaric acid to L-malic by sol-gel immobilized Saccharomyces cerevisiae in a supported liquid membrane bioreactor.
PubMed:Subulatin, an antioxidic caffeic acid derivative isolated from the in vitro cultured liverworts, Jungermannia subulata, Lophocolea heterophylla, and Scapania parvitexta.
PubMed:Novel morpholinone-based D-Phe-Pro-Arg mimics as potential thrombin inhibitors: design, synthesis, and X-ray crystal structure of an enzyme inhibitor complex.
PubMed:Quantitative determination of perfluorooctanoic acid ammonium salt in human serum by high-performance liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry.
PubMed:The DNA-polymerase inhibiting activity of poly(beta-l-malic acid) in nuclear extract during the cell cycle of Physarum polycephalum.
PubMed:Isolation and pharmacological activity of phenylpropanoid esters from Marrubium vulgare.
PubMed:L-malic acid biosensor for field-based evaluation of apple, potato and tomato horticultural produce.
PubMed:[Study on the optimal conditions in simultaneous reaction and separation for L-malic acid production].
PubMed:A Modular Enantioselective Approach to Construction of the Macrolactone Core of Polycavernoside A.
PubMed:Enantiomeric purity determination of malic acid in apple juices by multi-beam circular dichroism detection.
PubMed:Development and characterization of cross-linked poly(malate) microspheres with dipyridamole.
PubMed:Characterization of Schizosaccharomyces pombe malate permease by expression in Saccharomyces cerevisiae.
PubMed:The use of alternative technologies to develop malolactic fermentation in wine.
PubMed:Malo-ethanolic fermentation in grape must by recombinant strains of Saccharomyces cerevisiae.
PubMed:New phenolic constituents from the fruit juice of Phyllanthus emblica.
PubMed:Total synthesis of (-)-rosmarinecine by intramolecular cycloaddition of (S)-malic acid derived pyrroline N-oxide.
PubMed:A study into the role of L-aspartic acid on the metabolism of L-malic acid and D-glucose by Oenococcus oeni.
PubMed:Synthesis of N4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine analogues: succinamide, L-2-hydroxysuccinamide, and L-2-hydroxysuccinamic acid hydrazide analogues.
PubMed:Study of an enzyme membrane reactor with immobilized fumarase for production of L-malic acid.
PubMed:Stereoselective approach to hydroxyindolizidines: protection/deprotection of the nitrone functionality via cycloaddition/retrocycloaddition.
PubMed:The total synthesis of pantocin B.
PubMed:Phenylpropanoids from Ballota nigra L. inhibit in vitro LDL peroxidation.
PubMed:Isolation and antibacterial activity of phenylpropanoid derivatives from Ballota nigra.
PubMed:Formation of L-malic acid by yeasts of the genus Dipodascus.
PubMed:Kinetics, stereospecificity, and expression of the malolactic enzyme.
PubMed:Isolation of poly(beta-L-malic acid)-degrading bacteria and purification and characterization of the PMA hydrolase from Comamonas acidovorans strain 7789.
PubMed:[A system of coupled reactions for enzymatic synthesis of L-malate].
PubMed:Synthesis of 1-N-[(2S,4S)- and (2S,4R)-5-amino-4-fluoro-2-hydroxypentanoyl]dibekacins (study on structure-toxicity relationships).
PubMed:Bioconversion of fumaric acid to succinic acid by recombinant E. coli.
PubMed:Production of L-malic acid via biocatalysis employing wild-type and respiratory-deficient yeasts.
PubMed:Preparation of alkyl-substituted indoles in the benzene portion. Part 15. Asymmetric synthesis of (+)-duocarmycin SA using novel procedure for preparation of hydroxyindoles.
PubMed:Extracellular reduction of selenite by a novel marine photosynthetic bacterium.
PubMed:Overexpression of cytosolic malate dehydrogenase (MDH2) causes overproduction of specific organic acids in Saccharomyces cerevisiae.
PubMed:Derepressed utilization of L-malic acid and succinic acid by mutants of Pachysolen tannophilus.
PubMed:Structural basis for the molecular memory of imprinted proteins in anhydrous media.
PubMed:The cytosolic pathway of L-malic acid synthesis in Saccharomyces cerevisiae: the role of fumarase.
PubMed:Mode of action of the yeast Saccharomyces cerevisiae as a feed additive for ruminants.
PubMed:The proton motive force generated in Leuconostoc oenos by L-malate fermentation.
PubMed:Heat resistance of Escherichia coli O157:H7 in apple juice.
PubMed:(R-Z)-7,15-hexadecadien-4-olide, sex pheromone of the yellowish elongate chafer, Heptophylla picea.
PubMed:A cytotoxic principle of Tamarindus indica, di-n-butyl malate and the structure-activity relationship of its analogues.
PubMed:Fumarate hydration test for differentiation of Campylobacter and Helicobacter species.
PubMed:Effects of ethanol and acetic acid on the transport of malic acid and glucose in the yeast Schizosaccharomyces pombe: implications in wine deacidification.
PubMed:Functional expression in Saccharomyces cerevisiae of the Lactococcus lactis mleS gene encoding the malolactic enzyme.
PubMed:Histamine production by wine lactic acid bacteria: isolation of a histamine-producing strain of Leuconostoc oenos.
PubMed:Uniport of monoanionic L-malate in membrane vesicles from Leuconostoc oenos.
PubMed:Counteractive Effects of ABA and GA3 on Extracellular and Intracellular pH and Malate in Barley Aleurone.
PubMed:L-malic acid production by entrapped Saccharomyces cerevisiae into polyacrylamide gel beads.
PubMed:Detection of adulteration in apple juice by L-malic/total malic acid ratio: collaborative study.
PubMed:Cloning and sequence analysis of the gene encoding Lactococcus lactis malolactic enzyme: relationships with malic enzymes.
PubMed:Reversible enzymic protection of the alpha-amino group of amino acid derivatives using an aminopeptidase A.
PubMed:Antimicrobial activity of sulfur dioxide to certain lactic acid bacteria isolated from wines.
PubMed:A comparative study on the transport of L(-)malic acid and other short-chain carboxylic acids in the yeast Candida utilis: evidence for a general organic acid permease.
PubMed:L-malic acid production by an albino strain of Monascus araneosus.
PubMed:Hydroxycinnamic Acid Derivatives, Caffeoylmalic and New Caffeoylaldonic Acid Esters, from Chelidonium majus*,1.
PubMed:Purification and characterization of an aminopeptidase A from Staphylococcus chromogenes and its use for the synthesis of amino-acid derivatives and dipeptides.
PubMed:Production of L-malic acid.
PubMed:Utilization of tartaric acid and related compounds by yeasts: taxonomic implications.
PubMed:[Substrate specificity of phosphoribosyl-aminoimidazole-succinocarboxamide synthetase (SAICAR-synthetase) from Saccharomyces cerevisiae yeast].
PubMed:Molecular imprinting of proteins and other macromolecules resulting in new adsorbents.
PubMed:Low- and high-affinity transport systems for citric acid in the yeast Candida utilis.
PubMed:Effect of a Saccharomyces cerevisiae culture on lactate utilization by the ruminal bacterium Selenomonas ruminantium.
PubMed:L-malic acid production using immobilized Saccharomyces cerevisiae.
PubMed:Optimization of L-malic acid production by Aspergillus flavus in a stirred fermentor.
PubMed:Bacterial siderophores: structures of pyoverdins Pt, siderophores of Pseudomonas tolaasii NCPPB 2192, and pyoverdins Pf, siderophores of Pseudomonas fluorescens CCM 2798. Identification of an unusual natural amino acid.
PubMed:Inverse Diauxy in the Yeast Hansenula anomala: Mutants Derepressed for Malic Acid Utilization in the Presence of Glucose.
PubMed:Inducible overexpression of the FUM1 gene in Saccharomyces cerevisiae: localization of fumarase and efficient fumaric acid bioconversion to L-malic acid.
PubMed:Native agarose-polyacrylamide gel electrophoresis allowing the detection of aminopeptidase, dehydrogenase, and esterase activities at the nanogram level: enzymatic patterns in some Frankia strains.
PubMed:Transport of malic acid and other dicarboxylic acids in the yeast Hansenula anomala.
PubMed:A simple plate-assay for the screening of L-malic acid producing microorganisms.
PubMed:[Stability of biocatalysts on the basis of carrageenan-immobilized Escherichia coli during continuous synthesis of L-malic acid].
PubMed:Maloalcoholic fermentation by immobilized Schizosaccharomyces pombe.
PubMed:An unusual polyanion from Physarum polycephalum that inhibits homologous DNA polymerase alpha in vitro.
PubMed:Relative bioavailability of almitrine bismesylate in humans.
PubMed:Medium for Screening Leuconostoc oenos Strains Defective in Malolactic Fermentation.
PubMed:Apple juice composition: sugar, nonvolatile acid, and phenolic profiles.
PubMed:Malolactic enzyme in Lactobacillus murinus.
PubMed:[Enzymatic synthesis of L-malic acid from fumaric acid using immobilized Escherichia coli cells].
PubMed:L-malic-acid permeation in resting cells of anaerobically grown Saccharomyces cerevisiae.
PubMed:Stem infusions enhanced methionine content of soybean storage protein.
PubMed:Purification and characterization of hydroxycinnamoyl D-glucose. Quinate hydroxycinnamoyl transferase in the root of sweet potato, Ipomoea batatas Lam.
PubMed:Design and synthesis of new transition-state analogue inhibitors of aspartate transcarbamylase.
PubMed:[Fumarate hydratase activity of various Escherichia coli strains].
PubMed:A study of the maloalcoholic fermentation pathway in Schizosaccharomyces pombe.
PubMed:Fast atom bombardment mass spectrometry of malic acid analogues of angiotensin II.
PubMed:Immobilization of fumarase by entrapment of rat liver mitochondria in polyacrylamide gel using gamma rays.
PubMed:Cytosolic malate dehydrogenase in muscle extracts of Toxocara canis.
PubMed:A malic Acid permease in isolated vacuoles of a crassulacean Acid metabolism plant.
PubMed:[Effect of D,L-malic acid dibenzylhydrazide on changes in the antioxidizing activity of lipids and monoamine oxidase activity in mouse organs].
PubMed:Biochemical differences between serotypes of Cryptococcus neoformans.
PubMed:Evidence for a Functional myo-Inositol Oxidation Pathway in Lilium longiflorum Pollen.
PubMed:[Development of experimental brain tumors in modulated amine metabolism].
PubMed:[Study on L-malic acid catabolism by "Lactobacillus casei" cells immobilized into polyacrylamide gel lattice (author's transl)].
PubMed:Stimulatory Effect of Malo-Lactic Fermentation on the Growth Rate of Leuconostoc oenos.
PubMed:[Resistance to levomycetin and activity of several enzymes in Escherichia coli and the agent of plague].
PubMed:[The decomposition of L-malic acid by yeasts of various genera with malic enzyme (author's transl)].
PubMed:Carbonic acid from decarboxylation by "malic" enzyme in lactic acid bacteria.
PubMed:[Studies of the enzymes of Schizosaccharomyces acidodevoratus, decomposing L-malic acid].
PubMed:[Decomposition of L-malic acid by Saccharomyces cerevisiae during fermentation].
PubMed:Poly-(L)-malic acid; a new protease inhibitor from Penicillium cyclopium.
PubMed:[Automatic determination of L-malic acid].
PubMed:[The malate dehydrogenase and lactate dehydrogenase activity of bacteria, decomposing L-malic acid].
PubMed:Fixation of carbon dioxide in the dark by the malic enzyme of bean and oat stem rust uredospores.
PubMed:The permeability of two- and eight-cell mouse embryos to L-malic acid.
PubMed:Identification of malic acid from yeast.
PubMed:[Synthesis of malic enzyme and pH adaptation in bacteria metabolizing L-malic acid].
PubMed:[Morphology, metabolic physiology and characterization of the malic enzyme activity in bacteria decomposing L-malic acid].
PubMed:Organic acid production by Basidiomycetes. 3. Cultural conditions for L-malic acid production.
PubMed:[On the catabolism of L-malic acid by lactic acid bacteria. IV. The activity of intact cells of Lactobacillus plantarum with special consideration of pyruvic acid decarbosylation].
PubMed:Studies on the biochemistry of Penicillium charlesii. Influence of various dicarboxylic acids on galactocarolose synthesis.
PubMed:Effects of additives on the survival of lactic streptococci in frozen storage.
PubMed:Decomposition of L-malic acid by wine yeasts.
PubMed:[On the metabolism of L-malic acid in lactobacilli. 3. On the separation of the malic-enzyme activity from the oxaloacetic acid-decarboxylase activity in Lactobacillus plantarum "L"].
PubMed:[On the decomposition of L-malic acid by lactic acid bacteria. II. Comparative study of malate-decomposing enzymes in various species of Lactobacillus plantarum].
PubMed:Organic acid production by Basidiomycetes. I. Screening of acid-producing strains.
PubMed:[On the reduction of L-malic acid by lactic acid bacteria. I. On malate reducing enzymes of bacterium "L" with special attention to oxalacetate decarboxylase].
PubMed:[Nutritional requirements of yeasts Schizosaccharomyces acidodevoratus decomposing L-malic acid].
PubMed:Excretion of L-malic acid in the chicken.
PubMed:X-irradiation of L-malic acid in aqueous solutions.
PubMed:Studies on the extracellular cultivation of an intracellular parasite (avian malaria). II. The effects of malate and of coenzyme A concentrates.
PubMed:The decarboxylation of L-malic acid by Lactobacillus arabinosus.
Occurs naturally in apples and various other fruits. Flavour enhancer, pH control agent
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