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Apfelsure Produkt Beschreibung

Malic acid  Struktur
6915-15-7
CAS-Nr.
6915-15-7
Bezeichnung:
Apfelsure
Englisch Name:
Malic acid
Synonyma:
-MaL;malic;E 296;DL-Malic;FDA 2018;malicaci;DL-MALATE;NSC 25941;MALIC ACID;pomalusacid
CBNumber:
CB7220795
Summenformel:
C4H6O5
Molgewicht:
134.09
MOL-Datei:
6915-15-7.mol

Apfelsure Eigenschaften

Schmelzpunkt:
131-133 °C (lit.)
Siedepunkt:
167.16°C (rough estimate)
alpha 
[α]D20 -0.5~+0.5° (c=5, H2O)
Dichte
1.609
Dampfdichte
4.6 (vs air)
Dampfdruck
<0.1 mm Hg ( 20 °C)
Brechungsindex
1.3920 (estimate)
Flammpunkt:
203 °C
storage temp. 
2-8°C
Löslichkeit
methanol: 0.1 g/mL, clear, colorless
Aggregatzustand
neat
pka
3.4(at 25℃)
PH
2.3 (10g/l, H2O, 20℃)
Optische Aktivität
[α]/D 0.10 to +0.10°
Wasserlöslichkeit
558 g/L (20 ºC)
Merck 
14,5707
BRN 
1723539
CAS Datenbank
6915-15-7(CAS DataBase Reference)
NIST chemische Informationen
Hydroxybutanedioic acid(6915-15-7)
EPA chemische Informationen
Malic acid (6915-15-7)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,Xi
R-Sätze: 22-37/38-41-36/37/38-42/43-34
S-Sätze: 26-39-37/39-36-36/39
WGK Germany  1
RTECS-Nr. ON7175000
Selbstentzündungstemperatur 644 °F
TSCA  Yes
HS Code  29181980
Giftige Stoffe Daten 6915-15-7(Hazardous Substances Data)
Toxizität LD50 orally in Rabbit: > 3200 mg/kg
Bildanzeige (GHS)
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung P264, P270, P301+P312, P330, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H318 Verursacht schwere Augenschäden. Schwere Augenschädigung Kategorie 1 Achtung P280, P305+P351+P338, P310
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung
Sicherheit
P261 Einatmen von Staub vermeiden.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
P337+P313 Bei anhaltender Augenreizung: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.
P405 Unter Verschluss aufbewahren.

Apfelsure Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R22:Gesundheitsschädlich beim Verschlucken.
R37/38:Reizt die Atmungsorgane und die Haut.
R41:Gefahr ernster Augenschäden.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-Sätze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S39:Schutzbrille/Gesichtsschutz tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Chemische Eigenschaften

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.

Chemische Eigenschaften

White to nearly white crystals or crystal powder

Verwenden

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

Verwenden

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.

Verwenden

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.

Definition

ChEBI: A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.

Vorbereitung Methode

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

A colorless crystalline carboxylic acid that is found in unripe fruits. It tastes of apples and is used in food flavorings.

Biotechnologische Produktion

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.

Allgemeine Beschreibung

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

Pharmazeutische Anwendungen

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.

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.

Sicherheitsprofil

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.

Sicherheit(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

Lager

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.

läuterung methode

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.]

Inkompatibilitäten

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.

Apfelsure Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Apfelsure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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6915-15-7(Apfelsure)Verwandte Suche:


  • alpha-Hydroxysuccinic acid
  • alpha-hydroxysuccinicacid
  • Butanedioic acid, hydroxy-
  • commonmalicacid
  • Deoxytetraric acid
  • deoxytetraricacid
  • femanumber2655
  • hydroxy-butanedioicaci
  • Hydroxyethane-1,2-dicarboxylic acid
  • hydroxyethane-1,2-dicarboxylicacid
  • hydroxy-succinicaci
  • Kyselina hydroxybutandiova
  • Kyselina jablecna
  • kyselinahydroxybutandiova
  • kyselinajablecna
  • malic
  • N-Hydroxysuccinic acid
  • Pomalus acid
  • pomalusacid
  • Succinic acid, hydroxy-
  • (+/-)-2-HYDROXYSUCCINIC ACID
  • (+/-)-HYDROXYSUCCINIC ACID
  • (+/-)-HYDROXYBUTANEDIOIC ACID
  • DL-MALATE
  • DL-HYDROXYBUTANEDIOIC ACID
  • D,L-Malic acid NF
  • DL-Malic acid >=98% (capillary GC)
  • DL-Malic acid ReagentPlus(R), >=99%
  • DL-Malic acid Vetec(TM) reagent grade, 98%
  • Malic acid meets USP/NF testing specifications
  • L(+)-Maric acid
  • Malic acid impurity
  • DL-Malic acid meets analytical specification of FCC, E296, 99-100.5% (alkalimetric)
  • High quality organic DL-Malic acid 6915-15-7 kf-wang(at)kf-chem.com
  • DL-HYDROXYSUCOINIC ACID
  • DL-HYROXYBUTANEDIOIC ACID
  • DL-MALIC ACID FREE ACID
  • DL-MALIC ACID 99+% FCC
  • MALIC ACID, USP
  • DL(+-)-MALIC ACID EXTRA PURE, FCC
  • DL-MALIC ACID, 99+%
  • DL-Malic
  • 2-hydroxybutanedioic acid
  • MALICACIDANDITSCOMMONSALTS
  • (+/-)-MALIC ACID
  • MALIC ACID
  • MALIC ACID, DL-
  • (±)-2-Hydroxysuccinic acid, DL-Hydroxybutanedioic acid, DL-Malic acid
  • (±)-2-Hydroxysuccinic acid, DL-Hydroxybutanedioic acid
  • 1-Hydroxyethane-1,2-dicarboxylic acid
  • MALIC ACID, DL-(P)
  • DL-Malic acid, extra pure, NF, FCC, E 296
  • DL-Malic acid,(±)-2-Hydroxysuccinic acid, DL-Hydroxybutanedioic acid
  • Malic Acid (500 mg)
  • DL-Malic acid, 99+% 500GR
  • E 296
  • FDA 2018
  • Nanoveson M
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