E 296= MALIC ACID
CAS Number: 6915-15-7
EC Number: 230-022-8
Linear Formula: HO2CCH2CH(OH)CO2H
IUPAC name: 2-Hydroxybutanedioic acid
Molecular Weight: 134.09 g/mol
DESCRIPTION:
E 296 is an organic compound with the molecular formula C4H6O5.
E 296 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.
E 296 has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally.
The salts and esters of E 296 are known as malates.
The malate anion is an intermediate in the citric acid cycle.
E 296 is involved in the Krebs cycle.
This is a process the body uses to make energy.
E 296 is an organic compound.
E 296 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.
E 296 has two stereoisomeric forms (L- and D-enantiomers), although only the L-isomer exists naturally.
The salts and esters of Malic Acid are known as malates.
The malate anion is an intermediate in the citric acid cycle.
E 296 has a clean, smooth taste and persistent sourness, allowing it to be blended with multiple food acids, sugars, high intensity sweeteners and flavours to create unique taste experiences.
Not to be confused with Maleic Acid or Malonic Acid.
Malic acid is an organic compound also known by the name of "apple acid" and "fruit acid", and it is contained in many prepared foods.
This compound is found naturally in apple, and in particular in the skin, and other fruit.
Malic acid is a so-called alpha-hydroxy organic acid, and it also present in many plant and animal species.
This intermediate is the key element in the main cellular energy production cycle, the Krebs cycle (also known as the citric acid cycle).
E 296 is often present in the label of the food, but E 296 is not dangerous or toxic to human health.
Its purpose is to increase the acidity of food, giving more flavour, but it is also used as a flavouring substance and colour stabilizer.
This acidifying compound is widely used in the food industry and it is generally obtained through a chemical synthesis.
E296 is normally found in fruit juices - mostly of grape or apple - as well as in jellies, spreadable fruit, jams, wine and in some low calories foods.
In nature, the malic acid is contained in foods such as prunes, currants, tomatoes and even bananas, in small quantities.
E296 is closely related to acid and it is characterized by a sour, bitter, strong and penetrating taste.
E296 is an organic compound, which is the active ingredient in many sour or tart foods.
In nature E296 is present in large concentration on the apple skin and in a wide range of fruit and vegetable products, including plums, tomatoes, currant berries, bananas.
In addition to being an acid regulator, E296 is added to foods to give them a richer and more penetrating aroma.
E296 is more tart than either ascorbic or citric acid.
CAS Number: 6915-15-7
EC Number: 230-022-8
Linear Formula: HO2CCH2CH(OH)CO2H
IUPAC name: 2-Hydroxybutanedioic acid
Molecular Weight: 134.09 g/mol
PROPERTIES of E 296:
vapor density: 4.6 (vs air)
vapor pressure: <0.1 mmHg ( 20 °C)
Assay: ≥99%
Density: 1.601 g/ cu cm at 20 °C
Form: solid
autoignition temp.: 644 °F
Mp: 131-133 °C (lit.)
Solubility:
acetone: soluble 17.75g/100g at 20 °C(lit.)
diethyl ether: soluble 0.84g/100g at 20 °C(lit.)
dioxane: soluble 22.7 g/100g at 20 °C(lit.)
ethanol: soluble 45.53g/100g at 20 °C(lit.)
methanol: soluble 82.7 g/100g at 20 °C(lit.)
water: soluble 55.8g/100g at 20 °C(lit.)
benzene: insoluble(lit.)
Molecular Weight: 134.09 g/mol
XLogP3: -1.3
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 5
Rotatable Bond Count: 3
Exact Mass: 134.02152329 g/mol
Monoisotopic Mass: 134.02152329 g/mol
Topological Polar Surface Area: 94.8 Ų
Heavy Atom Count: 9
Formal Charge: 0
Complexity: 129
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Physical Description: White or nearly white crystalline powder or granules
Color/Form: Colorless crystals
Taste: Smoothly tart, Sour taste
Stability/Shelf Life:
Stable under recommended storage conditions
Decomposition:
When heated to decomposition it emits acrid smoke and irritating fumes.
pH:
pH of a 0.001% aqueous solution is 3.80, that of 0.1% solution is 2.80, and that of a 1.0% solution is 2.34
Heat of Combustion: -1.340 MJ/mol at 20 °C
Biochemistry of E 296:
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.
It 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.
CAS Number: 6915-15-7
EC Number: 230-022-8
Linear Formula: HO2CCH2CH(OH)CO2H
IUPAC name: 2-Hydroxybutanedioic acid
Molecular Weight: 134.09 g/mol
Production and main reactions of E 296:
Racemic malic acid is produced industrially by the double hydration of maleic anhydride.
In 2000, American production capacity was 5000 tons per year.
The enantiomers may be separated by chiral resolution of the racemic mixture.
S-Malic acid is obtained by fermentation of fumaric acid.
Self-condensation of malic acid in the presence of fuming sulfuric acid gives the pyrone coumalic acid:
Malic acid was important in the discovery of the Walden inversion and the Walden cycle, in which (−)-malic acid first is converted into (+)-chlorosuccinic acid by action of phosphorus pentachloride.
Wet silver oxide then converts the chlorine compound to (+)-malic acid, which then reacts with PCl5 to the (−)-chlorosuccinic acid.
The cycle is completed when silver oxide takes this compound back to (−)-malic acid.
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.
E 296 has a role as a food acidity regulator and a fundamental metabolite.
E 296 is a 2-hydroxydicarboxylic acid and a C4-dicarboxylic acid.
E 296 derives from a succinic acid.
E 296 is a conjugate acid of a malate(2-) and a malate.
USES of E 296:
E 296 is a substance found naturally in apples and pears.
E 296 is considered an alpha-hydroxy acid, a class of natural acids commonly used in skin-care products.
E 296 is a chemical found in certain fruits and wines.
E 296 is used to make medicine.
People take E 296 by mouth for tiredness and fibromyalgia.
In foods, E 296 is used as a flavoring agent to give food a tart taste.
In manufacturing, E 296 is used to adjust the acidity of cosmetics.
CAS Number: 6915-15-7
EC Number: 230-022-8
Linear Formula: HO2CCH2CH(OH)CO2H
IUPAC name: 2-Hydroxybutanedioic acid
Molecular Weight: 134.09 g/mol
E 296 IN FOOD:
Malic acid was first isolated from apple juice by Carl Wilhelm Scheele in 1785.
Antoine Lavoisier in 1787 proposed the name acide malique, which is derived from the Latin word for apple, mālum—as is its genus name Malus.
In German it is named Äpfelsäure (or Apfelsäure) after plural or singular of a sour thing from the apple fruit, but the salt(s) are called Malat(e).
Malic acid is the main acid in many fruits, including apricots, blackberries, blueberries, cherries, grapes, mirabelles, peaches, pears, plums, and quince and is present in lower concentrations in other fruits, such as citrus.
E 296 contributes to the sourness of unripe apples.
Sour apples contain high proportions of the acid.
E 296 is present in grapes and in most wines with concentrations sometimes as high as 5 g/l.
E 296 confers a tart taste to wine; the amount decreases with increasing fruit ripeness.
The taste of malic acid is very clear and pure in rhubarb, a plant for which it is the primary flavor.
E 296 is also a component of some artificial vinegar flavors, such as "salt and vinegar" flavored potato chips.
In citrus, fruits produced in organic farming contain higher levels of malic acid than fruits produced in conventional agriculture.
The process of malolactic fermentation converts malic acid to much milder lactic acid.
Malic acid occurs naturally in all fruits and many vegetables, and is generated in fruit metabolism.
Malic acid, when added to food products, is denoted by E number E296.
E 296 is sometimes used with or in place of the less sour citric acid in sour sweets.
These sweets are sometimes labeled with a warning stating that excessive consumption can cause irritation of the mouth.
E 296 is approved for use as a food additive in the EU, US and Australia and New Zealand (where it is listed by its INS number 296).
E 296 contains 10 kJ (2.39 kilocalories) of energy per gram.
Malic acid’s mellow, smooth, persistent sourness enhances the sensory experience of a variety of applications.
E 296 blends with other food acids, sugars, high-intensity sweeteners, flavors, and seasonings to bring the most true-to-fruit flavor experiences in foods, beverages, confections, and more.
Better Flavor, Easy Formulations:
E 296 balances or intensifies the impact of fruit flavors in food and beverage applications, and many times the amount of flavor needed in a formulation can be decreased for better economies.
From aroma to intensity to depth of flavor, many foods and beverages can achieve a better flavor experience—be it related to aroma, intensity, depth of flavor, aftertaste, or more—thanks to E 296.
Beverages:
Whether it’s a bubbly, low-calorie soda or a refreshing iced tea, malic acid enhances desired fruit flavors and masks off-notes from high-intensity sweeteners and other ingredients for a better taste, sip after sip.
Confectionery:
Tart and sweet hard candy; fruity, chewy gummies; and long-lasting chewing gums all benefit from enhanced and prolonged fruit flavors achieved by adding E 296.
Fruit Preparations & Preserves:
E 296 improves the sweet fruit spreads that complete our favorite food pairings—toast and jam, peanut butter and jelly—which enhances natural fruit flavors and stabilizes pH for a perfectly spreadable gel and thickness.
Desserts & Bakery:
Frozen and baked desserts like sherbets, flavored ices, jelly-filled doughnuts, and fruit-filled pies get a natural fruit flavor boost and a smooth, controlled gel with the addition of E 296.
Medicinal & Personal Care:
From fizzy tablets with cleaning power and gently rejuvenating face washes to fruity cough drops and palatable cough syrups, E 296 is used in many medical, personal care, and cosmetic applications as a functionally versatile and flavor-enhancing ingredient.
ADVANTAGES:
The E 296 in food provides a range of benefits as follows:
E 296 supports the body in the release of energy from food;
E 296 increases physical endurance of athletes and sportsmen;
E 296 provides valuable support during the hypoxic phase of training;
E 296 can relieve the symptoms of chronic fibromyalgia reducing pain.
For the reasons above, the consumption of food containing E 296 is highly recommended for people who practice sports at intense, competitive or professional level, since it is believed to increase the physical performance especially in cases of lack of oxygen in the cells.
E 296 can prolong sports performances especially when taken as a dietary supplement, during the hypoxic phases of the training.
E 296 in food – safety:
In terms of safety, we should remember that the E 296 in food can irritate eyes and skin, but E 296 does not cause damage to health.
On this point, Europe has not defined the reference values for the daily quantity ingested.
Health Benefits of E 296:
E 296 is found in fruits and vegetables and is produced naturally in the body when carbohydrates are converted into energy.
While some research suggests that E 296 supplements may help people with certain conditions, high-quality clinical trials are needed.
There's some evidence that E 296 supplements may offer these benefits:
Skin-Care Benefits:
When applied to the skin, malic acid is said to reduce signs of aging, remove dead skin cells, aid in the treatment of acne, and promote skin hydration.
A number of early studies published in the 1990s and early 2000s indicate that malic acid may be beneficial when applied to the skin.
In tests on animals and human cells, the studies' authors found that malic acid may help increase collagen production and reverse sun-induced signs of skin aging.
More recent research on topically applied malic acid includes a small study published in the Journal of Drugs in Dermatology in 2013.1 For the study, researchers assigned people with melasma (a common disorder marked by patches of abnormally dark skin) to a skin-care regimen that included the use of topical vitamin C and malic acid.
At an average follow-up of 26 months, the regimen was found to be an effective short-term treatment for melasma.
Physical Performance:
Malic acid is also used to boost sports performance when taken in supplement form.
E 296 is sometimes combined with creatine supplements in order to improve the body's absorption of creatine.
Proponents claim that malic acid can promote energy production, increase exercise endurance, and help fight off muscle fatigue.
For a study published in Acta Physiologica Hungarica in 2015, researchers investigated the effectiveness of a creatine-malate supplement in sprinters and long-distance runners.
After six weeks of supplementation combined with physical training, there was a significant increase in the physical performance in sprinters, measured by peak power, total work, body composition, and elevated growth hormone levels.
In long-distance runners, there was a significant increase in distance covered.
Kidney Stones:
E 296 is a precursor to citrate, a substance believed to prevent calcium from binding with other substances in urine that form kidney stones.
Citrate may also prevent crystals from getting bigger by preventing them from sticking together.
According to a preliminary laboratory study published in 2014, malic acid consumption may increase urine pH and citrate levels, making stone formation less likely.
malic acid supplementation may be useful for the conservative treatment of calcium kidney stones.
The high malic acid content in pears, future research should explore whether a diet supplemented with pears and low in meat and sodium may reduce stone formation.
Fibromyalgia:
Taking malic acid in combination with magnesium helped alleviate pain and tenderness in people with fibromyalgia.
For the study, researchers assigned 24 people with fibromyalgia to treatment with either a placebo or a combination of malic acid and magnesium.
After six months, those treated with the malic acid/magnesium combination showed a significant improvement in pain and tenderness.
However, there's a lack of more recent research on malic acid's effectiveness as a fibromyalgia treatment.
Dry Mouth:
The use of a one percent oral malic acid spray has been explored as a treatment for dry mouth.
A study published in Depression and Anxiety, for instance, evaluated a one percent malic acid spray compared to a placebo in people with dry mouth resulting from antidepressant use.
After two weeks of using the sprays when needed, those using the malic acid spray had improved dry mouth
Using a mouth spray or sucking on a tablet containing malic acid seems to improve symptoms of dry mouth better than using a saline mouth spray or citric acid oral rinse symptoms and increased saliva flow rates.
CAS Number: 6915-15-7
EC Number: 230-022-8
Linear Formula: HO2CCH2CH(OH)CO2H
IUPAC name: 2-Hydroxybutanedioic acid
Molecular Weight: 134.09 g/mol
E 296 SAFETY:
E 296 is generally recognized as safe (GRAS) by the United States Food and Drug Administration (FDA).
When a compound is given a GRAS designation, it means that experts have decided that E 296 poses little to no health risk at normal levels of consumption.
Malic acid has also been awarded a “green circle” by the Environmental Protection Agency (EPA). This simply means that, based on experimental data, the EPA isn’t concerned with the safety profile of this chemical.
Another promising data point: The fibromyalgia study referenced earlier suggests that fairly high doses of malic acid can be taken for up to six months without adverse effects.
These doses were orders of magnitude higher than what you’d find in foods and beverages.
Avoid getting E 296 in your eye or placing the undiluted chemical directly on your skin.
Beyond that, there’s little to worry about with E 296.
CAS Number: 6915-15-7
EC Number: 230-022-8
Linear Formula: HO2CCH2CH(OH)CO2H
IUPAC name: 2-Hydroxybutanedioic acid
Molecular Weight: 134.09 g/mol
Synonyms of E 296:
MeSH Entry Terms:
calcium (hydroxy-1-malate) hexahydrate
malate
malic acid
malic acid, (R)-isomer
malic acid, calcium salt, (1:1), (S)-isomer
malic acid, disodium salt
malic acid, disodium salt, (R)-isomer
malic acid, disodium salt, (S)-isomer
malic acid, magnesium salt (2:1)
malic acid, monopotassium salt, (+-)-isomer
malic acid, potassium salt, (R)-isomer
malic acid, sodium salt, (+-)-isomer
Depositor-Supplied Synonyms:
malic acid
DL-malic acid
6915-15-7
2-Hydroxysuccinic acid
2-Hydroxybutanedioic acid
617-48-1
malate
Butanedioic acid, hydroxy-
Kyselina jablecna
hydroxybutanedioic acid
hydroxysuccinic acid
Malic acid, DL-
Pomalus acid
Deoxytetraric acid
Hydroxybutandisaeure
alpha-Hydroxysuccinic acid
dl-Hydroxybutanedioic acid
Musashi-no-Ringosan
Caswell No. 537
DL-2-hydroxybutanedioic acid
FDA 2018
Monohydroxybernsteinsaeure
Succinic acid, hydroxy-
R,S(+-)-Malic acid
Kyselina jablecna [Czech]
Malic acid, L-
Hydroxy Succinic Acid
FEMA No. 2655
2-Hydroxyethane-1,2-dicarboxylic acid
Kyselina hydroxybutandiova [Czech]
Malic acid [NF]
EPA Pesticide Chemical Code 051101
Apple acid
AI3-06292
butanedioic acid, 2-hydroxy-
BUTANEDIOIC ACID, HYDROXY-, (S)-
MLS000084707
CHEBI:6650
(+/-)-2-Hydroxysuccinic acid
(+-)-1-Hydroxy-1,2-ethanedicarboxylic acid
NSC25941
Malic acid (NF)
MFCD00064212
NSC-25941
Butanedioic acid, 2-hydroxy-, (2S)-
E296
SMR000019054
DL-Apple Acid
DSSTox_CID_7640
(R)-Hydroxybutanedioic acid
(S)-Hydroxybutanedioic acid
DSSTox_RID_78538
DSSTox_GSID_27640
(+-)-Malic acid
R-Malic acid
Malicum acidum
FEMA Number 2655
Malic acid, D-
CAS-6915-15-7
CCRIS 2950
CCRIS 6567
L-(-)-MalicAcid
Malic acid L-(-)-form
Hydroxysuccinnic acid (-)
HSDB 1202
DL-hydroxysuccinic acid
Kyselina hydroxybutandiova
EINECS 210-514-9
EINECS 230-022-8
NSC 25941
(+-)-Hydroxysuccinic acid
Aepfelsaeure
NSC 9232
NSC-9232
Pomalous acid
d,l-malic acid
Hydroxybutanedioic acid, (+-)-
H2mal
Racemic malic acid
.+-.-Malic acid
143435-96-5
(+/-)-Malic acid
Opera_ID_805
2-hydroxyl-succinic acid
DL-Malic acid, 99%
MALIC ACID,(DL)
2-Hydroxydicarboxylic acid
SCHEMBL856
2-hydroxy-butanedioic acid
bmse000046
bmse000904
EC 210-514-9
EC 230-022-8
Malic acid-, (L-form)-
DL-Malic acid, >=99%
HYOSCYAMINEHYDROBROMIDE
Oprea1_130558
Oprea1_624131
DL-Malic acid-2-[13C]
DL-HYDROXYSUCOINIC ACID
Butanedioic acid, (.+-.)-
DL(+/-)-MALIC ACID
GTPL2480
Hydroxybutanedioic acid, (-)-
INS NO.296
2-HYDROXY-SUCCINIC ACID
DL-HYROXYBUTANEDIOIC ACID
CHEMBL1455497
DTXSID0027640
BDBM92495
INS NO. 296
INS-296
DL-Malic acid, FCC, >=99%
HMS2358H06
HMS3371C13
DL-Malic acid, analytical standard
ACN-S004262
HY-Y1311
STR03457
(+/-)-HYDROXYSUCCINIC ACID
Tox21_201536
Tox21_300372
s9001
STL283959
AKOS000120085
AKOS017278471
(+/-)-HYDROXYBUTANEDIOIC ACID
AM81418
CCG-266122
DB12751
MCULE-5852208511
DL-Malic acid, ReagentPlus(R), 99%
NCGC00043225-02
NCGC00043225-03
NCGC00254259-01
NCGC00259086-01
DL-Malic acid, >=98% (capillary GC)
SY003313
SY009804
DL-Malic acid, ReagentPlus(R), >=99%
DB-016133
DL-Malic acid 1000 microg/mL in Methanol
DL-Malic acid, USP, 99.0-100.5%
CS-0017784
E 296
E-296
EU-0067046
FT-0605225
FT-0625484
FT-0625485
FT-0625539
FT-0632189
M0020
DL-Malic acid, SAJ first grade, >=99.0%
A19426
C00711
C03668
D04843
DL-Malic acid 1000 microg/mL in Acetonitrile
DL-Malic acid, Vetec(TM) reagent grade, 98%
M-0825
AB00443952-12
Malic acid, meets USP/NF testing specifications
4-ethoxyphenyltrans-4-propylcyclohexanecarboxylate
L023999
Q190143
Q-201028
0C9A2DC0-FEA2-4864-B98B-0597CDD0AD06
F0918-0088
Z940713496
Malic acid, United States Pharmacopeia (USP) Reference Standard
Malic acid, Pharmaceutical Secondary Standard; Certified Reference Material
DL-Malic acid, meets analytical specification of FCC, E296, 99-100.5% (alkalimetric)