ChemicalBook > CAS DataBase List > Malic acid

Malic acid

Product Name
Malic acid
CAS No.
6915-15-7
Chemical Name
Malic acid
Synonyms
malic;DL-Malic;DL-MALATE;hydroxy-butanedioicaci;DL-MALIC ACID FREE ACID;alpha-Hydroxysuccinic acid;-MaL;E 296;FDA 2018;malicaci
CBNumber
CB7220795
Molecular Formula
C4H6O5
Formula Weight
134.09
MOL File
6915-15-7.mol
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Malic acid Property

Melting point:
131-133 °C (lit.)
Boiling point:
167.16°C (rough estimate)
alpha 
[α]D20 -0.5~+0.5° (c=5, H2O)
Density 
1.609
vapor density 
4.6 (vs air)
vapor pressure 
<0.1 mm Hg ( 20 °C)
refractive index 
1.3920 (estimate)
Flash point:
203 °C
storage temp. 
2-8°C
solubility 
methanol: 0.1 g/mL, clear, colorless
pka
3.4(at 25℃)
color 
White to Almost white
Odor
at 100.00 %. odorless
PH
3.33(1 mM solution);2.74(10 mM solution);2.21(100 mM solution);
optical activity
[α]/D 0.10 to +0.10°
Odor Type
odorless
Water Solubility 
558 g/L (20 ºC)
Merck 
14,5707
BRN 
1723539
LogP
-6.14 at 20℃
CAS DataBase Reference
6915-15-7(CAS DataBase Reference)
NIST Chemistry Reference
Hydroxybutanedioic acid(6915-15-7)
EPA Substance Registry System
Malic acid (6915-15-7)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
22-37/38-41-36/37/38-42/43-34
Safety Statements 
26-39-37/39-36-36/39
WGK Germany 
1
RTECS 
ON7175000
Autoignition Temperature
644 °F
TSCA 
Yes
HS Code 
29181980
Hazardous Substances Data
6915-15-7(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: > 3200 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W265501
Product name
DL-Malic acid
Purity
99%
Packaging
1kg
Price
$76.5
Updated
2024/03/01
Sigma-Aldrich
Product number
W265501
Product name
DL-Malic acid
Purity
99%
Packaging
5kg
Price
$150
Updated
2024/03/01
Sigma-Aldrich
Product number
W265501
Product name
DL-Malic acid
Purity
99%
Packaging
10Kg
Price
$171
Updated
2024/03/01
Sigma-Aldrich
Product number
8.14737
Product name
DL-Malic acid
Purity
forsynthesis
Packaging
1kg
Price
$84.2
Updated
2024/03/01
Sigma-Aldrich
Product number
94916
Product name
DL-Malic acid
Purity
analytical standard
Packaging
100MG
Price
$73.6
Updated
2024/03/01
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Malic acid Chemical Properties,Usage,Production

Chemical Properties

White or nearly white, crystalline powder or granules having a slight odor and a strongly acidic taste. It is hygroscopic. The synthetic material produced commercially in Europe and the USA is a racemic mixture, whereas the naturally occurring material found in apples and many other fruits and plants is levorotatory.

Uses

Malic Acid is an acidulant that is the predominant acid in apples. it exists as white crystalline powder or granules and is considered hygroscopic. as compared to citric acid, it is slightly less soluble but is still readily soluble in water with a solubility of 132 g/100 ml at 20°c. it has a stronger apparent acid taste and has a longer taste retention than citric acid which peaks faster but does not mask the aftertaste as effectively. a quantity of 0.362–0.408 kg of malic acid is equivalent to 0.453 kg of citric acid and to 0.272–0.317 kg of fumaric acid in tartness. at temperatures above 150°c it begins to lose water very slowly to yield fumaric acid. it is used in soft drinks, dry-mix beverages, puddings, jellies, and fruit filling. it is used in hard can- dies because it has a lower melting point (129°c) than citric acid which improves the ease of incorporation.

Uses

Malic acid, HOOCCH(OH).CH2COOH, also known as hydroxysuccinic acid, is a colorless solid. It is soluble in water and alcohol. Malic acid exists in two optically active forms and a racemic mixture. It is used in medicine and found in apples and other fruits.
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

Uses

malic acid is the third smallest alpha hydroxy acid in terms of molecular size. Although it is used in numerous cosmetic products, particularly those indicating a “fruit acid” content and generally designed for anti-aging, unlike glycolic and lactic acids, its skin benefits have not been extensively studied. Some formulators consider it difficult to work with, particularly when compared to other AHAs, and it can be somewhat irritating. It is rarely used as the only AHA in a product. It is found naturally occurring in apples.

Production Methods

Malic acid is manufactured by hydrating maleic and fumaric acids in the presence of suitable catalysts. The malic acid formed is then separated from the equilibrium product mixture.

Definition

ChEBI: Malic acid is a 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group. It has a role as a food acidity regulator and a fundamental metabolite. It is a 2-hydroxydicarboxylic acid and a C4-dicarboxylic acid. It derives from a succinic acid. It is a conjugate acid of a malate(2-) and a malate.

Biotechnological Production

DL-malic acid as well as L-malic acid can be used in beverage, food, and animal nutrition. DL-malic acid is mainly derived from chemical synthesis, whereas L-malic acid is produced biotechnologically by enzymatic or fermentative processes.
Fumaric acid can be converted to L-malic acid using fumarases. Different microorganisms (e.g. Brevibacterium flavum, Brevibacterum ammoniagenes, and Corynebacterium species) are able to form naturally high amounts of fumarase intracellularly. For example, B. flavum has been immobilized in j-carrageenan and polyethyleneimine for whole-cell biocatalysis. A fumarase activity of 2.16 mmol.ml(gel)-1.h -1 at 55 C has been reported. This process has been used to produce 30 metric tons of L-malic acid per month in a continuous process with a 1,000 L column fed at a flow rate of 450 L.h-1 of 1 M sodium fumarate solution. Genetic engineering has been used to improve productivity, by which S. cerevisiae is modified to overexpress fumarase. With this method, a conversion rate of 65 mmol.g-1.h -1 has been observed.
Another possibility is the cultivation of an L-malic acid forming microorganism (e.g. Aspergillus flavus or Schizophyllum commune). The best results have been achieved by cultivation of A. flavus on glucose.Afinal product concentration of 113 g.L-1 with a yield of 1.26 mol of malic acid per mole of glucose and a productivity of 0.59 g.L-1.h-1 has been measured. Moreover, new biotechnological routes have been described using metabolically engineered S. cereviciae. In batch cultivations, concentrations up to 59 g.L-1 with a yield of 0.42 mol of malic acid per mole of glucose and a productivity of 0.19 g.L-1.h-1 have been observed.

General Description

The chiral resolution of DL-malic acid by ligand-exchange capillary electrophoresis was studied.

Flammability and Explosibility

Non flammable

Pharmaceutical Applications

Malic acid is used in pharmaceutical formulations as a generalpurpose acidulant. It possesses a slight apple flavor and is used as a flavoring agent to mask bitter tastes and provide tartness. Malic acid is also used as an alternative to citric acid in effervescent powders, mouthwashes, and tooth-cleaning tablets.
In addition, malic acid has chelating and antioxidant properties. It may be used with butylated hydroxytoluene as a synergist in order to retard oxidation in vegetable oils. In food products it may be used in concentrations up to 420 ppm.
Therapeutically, malic acid has been used topically in combination with benzoic acid and salicylic acid to treat burns, ulcers, and wounds. It has also been used orally and parenterally, either intravenously or intramuscularly, in the treatment of liver disorders, and as a sialagogue.

Biochem/physiol Actions

Malic acid is a dicarboxylic acid and an important regulatory metabolite. It has been implicated in process of fruit ripening. Malic acid is important for the starch metabolism; low malic acid content results in transient accumulation of starch. Mitochondrial-malate metabolism modulates ADP-glucose pyrophosphorylase activity and redox status of plastids.

Mechanism of action

Malic acid is absorbed from the gastrointestinal tract from whence it is transported via the portal circulation to the liver. There are a few enzymes that metabolize malic acid. Malic enzyme catalyzes the oxidative decarboxylation of L-malate to pyruvate with concomitant reduction of the cofactor NAD+ (oxidized form of nicotinamide adenine dinucleotide) or NADP+ (oxidized form of nicotinamide adenine dinucleotide phosphate). These reactions require the divalent cations magnesium or manganese. Three isoforms of malic enzyme have been identified in mammals: a cytosolic NADP+-dependent malic enzyme, a mitochondrial NADP+- dependent malic enzyme and a mitochondrial NAD(P)+-dependent malic enzyme. The latter can use either NAD+ or NADP+ as the cofactor but prefers NAD+. Pyruvate formed from malate can itself be metabolized in a number of ways, including metabolism via a number of metabolic steps to glucose. Malate can also be metabolized to oxaloacetate via the citric acid cycle. The mitochondrial malic enzyme, particularly in brain cells may play a key role in the pyruvate recycling pathway, which utilizes dicarboxylic acids and substrates, such as glutamine, to provide pyruvate to maintain the citric acid cycle activity when glucose and lactate are low.

Safety Profile

A poison by intraperitoneal route. Moderately toxic by ingestion. A skin and severe eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety

Malic acid is used in oral, topical, and parenteral pharmaceutical formulations in addition to food products, and is generally regarded as a relatively nontoxic and nonirritant material. However, concentrated solutions may be irritant.
LD50 (rat, oral): 1.6 g/kg(3)
LD50 (rat, IP): 0.1 g/kg

storage

Malic acid is stable at temperatures up to 150°C. At temperatures above 150°C it begins to lose water very slowly to yield fumaric acid; complete decomposition occurs at about 180°C to give fumaric acid and maleic anhydride.
Malic acid is readily degraded by many aerobic and anaerobic microorganisms. Conditions of high humidity and elevated temperatures should be avoided to prevent caking.
The effects of grinding and humidity on malic acid have also been investigated.
The bulk material should be stored in a well-closed container, in a cool, dry place.

Purification Methods

Crystallise the acid from acetone, then from acetone/CCl4, or from ethyl acetate by adding pet ether (b 60-70o). Dry it at 35o under 1mm pressure to avoid formation of the anhydride. [Beilstein 3 IV 1124.]

Incompatibilities

Malic acid can react with oxidizing materials. Aqueous solutions are mildly corrosive to carbon steels.

Regulatory Status

GRAS listed. Both the racemic mixture and the levorotatory isomer are accepted as food additives in Europe. The DL and L forms are included in the FDA Inactive Ingredients Database (oral preparations). Included in nonparenteral and parenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Nonmedicinal Ingredients.

Malic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Malic acid manufacturers

Hebei Saisier Technology Co., LTD
Product
Malic acid 6915-15-7
Price
US $6.00/KG
Min. Order
1KG
Purity
More than 99%
Supply Ability
2000KG/MONTH
Release date
2024-04-22
Hebei Yime New Material Technology Co., Ltd.
Product
malic acid 6915-15-7
Price
US $1800.00/T
Min. Order
20T
Purity
99%
Supply Ability
100tons
Release date
2023-11-16
Ouhuang Engineering Materials (Hubei) Co., Ltd
Product
(±)-Malic Acid 6915-15-7
Price
US $15.00/kg
Min. Order
1kg
Purity
99.912%
Supply Ability
10ton
Release date
2024-04-17

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