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CAS: 97-67-6
MF: C4H6O5
MW: 134.09
EINECS: 202-601-5
Description
L-Malic acid is nearly odorless with a tart, acidic taste.
L-Malic acid is nonpungent.
L-Malic acid is an organic acid that is commonly found in wine.
L-Malic acid plays an important role in wine microbiological stability.
L-Malic acid can be prepared by hydration of maleic acid; by fermentation from sugar.
Occurs in maple sap, apple, melon, papaya, beer, grape wine, cocoa, sake, kiwifruit and chicory root.
L-Malic acid is an organic compound with the molecular formula C4H6O5.
L-Malic acid is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive.
L-Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally.
The salts and esters of L-Malic acid are known as malates.
The malate anion is an intermediate in the citric acid cycle.
L-Malic acid, a hydroxydicarboxylic acid, is found in all forms of life.
L-Malic acid exists naturally only as the L-enantiomer.
L-Malic acid should not be confused with the similar sounding maleic and malonic acids.
L-Malic acid is L-hydroxysuccinic acid, by enzyme engineering method or fermentation method and separation and purification.
The content of C4H6Os shall not be less than 99.0% calculated as anhydrous.
L-Malic acid gives many fruits, particularly apples, their characteristic flavor.
L-Malic acid is often referred to as “apple acid”.
The word malic is derived from the Latin mālum, for which Malus, the genus that contains all apple species, is also named.
L-Malic acid is a dicarboxylic acid that is found in many fruits and vegetables.
L-Malic acid is the substrate for the enzyme malate dehydrogenase, which catalyzes the oxidation of L-malate to oxaloacetate.
L-Malic acid is used to study mitochondrial function, as it can be used as an alternative energy source.
The L-malic acid monosodium salt (LAM) has been shown to be effective in preventing muscle damage caused by exercise.
This may be due to L-Malic acid's ability to decrease oxidative stress and increase ATP production through increased mitochondrial activity.
L-Malic acid also has been shown to promote photoreceptor cell survival and improve retinal function in animals with damaged photoreceptors, although it does not have any effect on normal animal eyes.
L-Malic acid, is an alpha-hydroxy organic acid, is sometimes referred to as a fruit acid.
L-Malic acid is found in apples and other fruits.
L-Malic acid is also found in plants and animals, including humans.
In fact, L-Malic acid, in the form of its anion malate, is a key intermediate in the major biochemical energy-producing cycle in cells known as the citric acid or Krebs cycle located in the cells' mitochondria.
L-Malic acid is used in many food products and is a very popular product in beverages and sweets.
L-Malic acid, also known as apple acid and hydroxysuccinic acid, is a chiral molecule.
L-Malic acid Chemical Properties
Melting point: 101-103 °C (lit.)
alpha: -2 º (c=8.5, H2O)
Boiling point: 167.16°C (rough estimate)
Density: 1.60
Vapor pressure: 0Pa at 25℃
FEMA: 2655 | L-MALIC ACID
Refractive index: -6.5 ° (C=10, Acetone)
Fp: 220 °C
Storage temp.: Store below +30°C.
Solubility H2O: 0.5 M at 20 °C, clear, colorless
Form: Powder
Color: White
Specific Gravity: 1.595 (20/4℃)
PH: 2.2 (10g/l, H2O, 20℃)
pka: (1) 3.46, (2) 5.10(at 25℃)
Optical activity: [α]20/D 30±2°, c = 5.5% in pyridine
Water Solubility: soluble
Merck: 14,5707
JECFA Number: 619
BRN: 1723541
InChIKey: BJEPYKJPYRNKOW-REOHCLBHSA-N
LogP: -1.68
CAS DataBase Reference: 97-67-6(CAS DataBase Reference)
NIST Chemistry Reference: L-Malic acid, hydroxy-, (s)-(97-67-6)
EPA Substance Registry System: L-Malic acid, 2-hydroxy-, (2S)- (97-67-6)
L-Malic acid is nearly odorless (sometimes a faint, acrid odor).
This compound has a tart, acidic, nonpungent taste.
Uses
L-Malic acid is used as a food additive, Selective α-amino protecting reagent for amino acid derivatives.
Versatile synthon for the preparation of chiral compounds including κ-opioid receptor agonists, 1α,25-dihydroxyvitamin D3 analogue, and phoslactomycin B.
The naturally occuring isomer is the L-form which has been found in apples and many other fruits and plants.
Selective α-amino protecting reagent for amino acid derivatives.
Versatile synthon for the preparation of chiral compounds including κ-opioid rece
Intermediate in chemical synthesis.
Chelating and buffering agent.
Flavoring agent, flavor enhancer and acidulant in foods.
L-Malic acid may improve exercise performance by boosting energy and decreasing muscle fatigue.
L-Malic acid also enhances the absorption of other sports performance enhancers like creatine and citrulline.
One study found that a creatine-malate combination improved several aspects of athletes’ running performance, including peak power, distance traveled, hormone levels, and total work.
Bonding L-Malic acid with citrulline produces citrulline malate.
The L-Malic acid enhances citrulline’s innate ability to improve nitric oxide levels, remove muscle waste, increase energy, and reduce muscle soreness.
L-Malic acid may improve dry mouth, dry mouth caused by medication in particular.
L-Malic acid helps produce more saliva due to its sour flavor.
One six-week study examined the effects of a L-Malic acid spray solution on dry mouth compared to a placebo.
The L-Malic acid group had noticeably improved dry mouth symptoms and better saliva flow than the placebo group.
Another two-week trial produced similar results.
Most individuals tolerate malic acid well, given that L-Malic acid’s a common compound in many fruits and vegetables.
L-Malic acid may cause mild side effects, including nausea, diarrhea, and headaches.
Individuals taking medications to lower their blood pressure should consult with a physician before taking malic acid supplements, as they may lower blood pressure.
Kidney stones are painful and can affect many people.
L-Malic acid has been researched for its potential role in preventing and treating kidney stones.
In one preliminary study set in a lab, L-Malic acid was found to increase urine pH levels, making kidney stone formation less likely.
The researchers concluded that L-Malic acid supplementation might help treat calcium kidney stones.4
A 2016 review on the importance of a healthy diet to prevent kidney stones suggested pears could be a potential treatment option.
Per the review, the L-Malic acid in pears may be used to prevent the formation of kidney stones.
This is because L-Malic acid is a precursor for citrate, a compound that inhibits crystal growth in the kidneys.
L-malic acid contains natural emollient ingredients, which can remove wrinkles on the skin surface, make the skin become tender and white, smooth and elastic, so in the cosmetic formula favored; L-malic acid can be formulated a variety of flavors, spices, for a variety of daily chemical products, such as toothpaste, shampoo, etc; it is used abroad to replace citric acid as a new type of detergent additive for the synthesis of high-grade special detergents.
L-malic acid can be used in pharmaceutical preparations, tablets, syrup, can also be mixed into the amino acid solution, can significantly improve the absorption rate of amino acids; L-malic acid can be used for the treatment of liver disease, anemia, low immunity, uremia, hypertension, liver failure and other diseases, and can reduce the toxic effect of anticancer drugs on normal cells; Can also be used for the preparation and synthesis of insect repellents, anti-Tartar agents.
In addition, L-malic acid can also be used as industrial cleaning agent, resin curing agent, synthetic material plasticizer, feed additive, etc.
Biochem/physiol Actions
L-Malic acid is a part of cellular metabolism.
L-Malic acid's application is recognized in pharmaceutics.
L-Malic acid is useful in the treatment of hepatic malfunctioning, effective against hyper-ammonemia.
L-Malic acid is used as a part of amino acid infusion.
L-Malic acid also serves as a nanomedicine in the treatment of brain neurological disorders.
A TCA (Krebs cycle) intermediate and partner in the L-Malic acid aspartate shuttle.
L-Malic acid is the naturally occurring form, whereas a mixture of L- and D-malic acid is produced synthetically.
Malate plays an important role in biochemistry.
In the C4 carbon fixation process, malate is a source of CO2 in the Calvin cycle.
In the citric acid cycle, (S)-malate is an intermediate, formed by the addition of an -OH group on the si face of fumarate.
L-Malic acid can also be formed from pyruvate via anaplerotic reactions.
Malate is also synthesized by the carboxylation of phosphoenolpyruvate in the guard cells of plant leaves.
Malate, as a double anion, often accompanies potassium cations during the uptake of solutes into the guard cells in order to maintain electrical balance in the cell.
The accumulation of these solutes within the guard cell decreases the solute potential, allowing water to enter the cell and promote aperture of the stomata.
Precautions
In 2022, an expert panel reviewed L-Malic acid and found it safe to use in cosmetics.
Besides a few side effects, L-Malic acid supplements are not known to cause any other safety concerns.
However, there is insufficient information to ensure L-Malic acid's safety in certain groups.
Because of this, L-Malic acid's best to be extra cautious and avoid using malic acid supplements during pregnancy or lactation.
There is also little evidence regarding the use of L-Malic acid in children.
Consult with your child's healthcare provider for professional advice.
The L-Malic acid in amounts found in food is generally safe for everyone.
L-Malic acid has also been deemed safe as a food additive, flavor enhancer, and pH controller.
Keep in mind that L-Malic acid supplements should not substitute standard care.
Self-treating a condition and avoiding or delaying medical care may have serious consequences.
Production Method
L-Malic acid widely exists in nature, is the product of animal and plant metabolism, is the main acid component in Apple.
The immature fruit juice of apple, grape and peach is boiled, lime water is added to form calcium salt precipitate, and then L-Malic acid is converted into lead salt, and then treated to form free acid, and L-malic acid can be obtained.
Fermentation method is also possible to achieve industrialization, the use of mutant yeast strains for fermentation, can obtain L-malic acid-based special fungi for acid, or use to produce malic acid-based special fungi for fermentation, L-malic acid can be obtained, but the process is more complicated than the synthesis method, and the cost is higher.
L-malic acid is produced by biosynthesis in Japan.
The Brevibacterium aminophenol cells (breridacterium ammoni-agenes cell) were first fixed with polyacrylamides.
A suspension of the cells in physiological saline was mixed with an acrylic acid amide and an appropriate cross-linking agent and a polymerization promoter, and the resulting gel was made into 3mm diameter particles.
After washing, the solution was soaked in sodium fumarate containing about 0.3 bovine bile and kept at 37 °c for 20H.
The cells treated in this way were used as a filler for the reaction column.
1L of sodium fumarate containing 1mol was passed through a reaction column at 37 ° C.
And the malic acid was separated from the effluent in the usual manner to produce a pharmaceutical grade product of L-malic acid from fumaric acid in a yield of about 70%.
Synonyms
97-67-6
L-Malic acid
L-(-)-Malic acid
(S)-2-hydroxysuccinic acid
(2S)-2-Hydroxybutanedioic acid
(S)-Malic acid
L(-)-Malic acid
Apple acid
(-)-Malic acid
L-Apple acid
(-)-Hydroxysuccinic acid
L-malate
S-(-)-Malic acid
L-Hydroxybutanedioic acid
S-2-Hydroxybutanedioic acid
Butanedioic acid, hydroxy-, (2S)-
Malic acid, L-
L-2-Hydroxybutanedioic acid
(S)-(-)-Hydroxysuccinic acid
CHEBI:30797
(-)-L-Malic acid
(S)-malate
Malic acid L-(-)-form
Hydroxysuccinnic acid (-)
L-Hydroxysuccinic acid
J3TZF807X5
CHEMBL1234046
NSC923
NSC-9232
MFCD00064213
26999-59-7
Butanedioic acid, 2-hydroxy-, (2S)-, homopolymer
NSC 9232
Butanedioic acid, 2-hydroxy-, (2S)-
(S)-Hydroxybutanedioic acid
MALATE ION
(-)-(S)-Malic acid
Hydroxybutanedioic acid, (-)-
UNII-J3TZF807X5
malic-acid
Hydroxybutanedioic acid, (S)-
laevo-malic acid
2yfa
4elc
4ipi
4ipj
L-Maleic Acid
L-Hydroxysuccinate
2-Hydroxybutanedioic acid, (S)-
(S)-(-)-2-Hydroxysuccinic acid
(2s)-malic acid
EINECS 202-601-5
L-Hydroxybutanedioate
nchembio867-comp7
L-(-) malic acid
(-)-Hydroxysuccinate
L-(-)-Apple Acid
S-(-)-Malate
(S)-Hydroxybutanedioate
S-2-Hydroxybutanedioate
(-)-(S)-Malate
(S)-(-)-malic acid
(S)-hydroxy-Butanedioate
(S)-Hydroxysuccinic acid
L(-)MALIC ACID
(S)-2-hydroxysuccinicacid
bmse000238
MALIC ACID [HSDB]
MALIC ACID, (L)
(S)-(-)-Hydroxysuccinate
L-MALIC ACID [FHFI]
(S)-hydroxy-Butanedioic acid
SCHEMBL256122
L-MALIC ACID [WHO-DD]
MALIC ACID, L- [II]
(-)-(s)-hydroxybutanedioic acid
DTXSID30273987
ZINC895074
(2S)-(-)-hydroxybutanedioic acid
AMY40197
HY-Y1069
BDBM50510127
s6292
AKOS006346693
CS-W020132
MALIC ACID L-(-)-FORM [MI]
L-(-)-Malic acid, BioXtra, >=95%
AS-18628
L-(-)-Malic acid, >=95% (titration)
(-)-1-Hydroxy-1,2-ethanedicarboxylic acid
M0022
C00149
L-(-)-Malic acid, purum, >=99.0% (T)
L-(-)-Malic acid, ReagentPlus(R), >=99%
M-0850
35F9ECA9-BBE6-463D-BF3F-275FACC5D14E
L-(-)-Malic acid, SAJ special grade, >=99.0%
L-(-)-Malic acid, Vetec(TM) reagent grade, 97%
Q27104150
(S)-(-)-2-Hydroxysuccinic acid, L-Hydroxybutanedioic acid
L-(-)-Malic acid, 97%, optical purity ee: 99% (GLC)
L-(-)-Malic acid, certified reference material, TraceCERT(R)
L-(-)-Malic acid, BioReagent, suitable for cell culture, suitable for insect cell culture
