Malic Acid Overview
Malic Acid is an organic compound, a dicarboxylic acid that is the active ingredient in many sour and tart foods. Malic Acid is generated during fruit metabolism and occurs naturally in all fruits and many vegetables.
The pleasant, refreshing experience of biting into a juicy apple or cherry is partly caused by Malic Acid. Its mellow, smooth, persistent sourness can be blended with multiple food acids, sugars, high intensity sweeteners, flavors and seasonings to create distinctive taste experiences in foods, beverages and confections.
Malic Acid is formed in metabolic cycles in the cells of plants and animals, including humans. The compound provides cells with energy and carbon skeletons for the formation of amino acids. The human body produces and breaks down relatively large amounts of Malic Acid every day.
Malic Acid contributes to the sourness of green apples. It is present in grapes and gives a tart taste to wine. When added to food products, Malic Acid is the source of extreme tartness. It is used with or in place of the less sour citric acid in sour sweets.
Malic Acid is used as a flavor enhancer in food preparation for confectionaries, beverages, fruit preparations and preserves, desserts, and bakery products. It is also essential in the preparation of medical products such as throat lozenges, cough syrups, effervescent powdered preparations, toothpaste and mouthwash. Additionally, Malic Acid is used in the manufacture of skin care products to rejuvenate and improve skin conditions.
About Malic Acid
History
Malic Acid is as old as fruit and vegetables. However, it wasn't isolated from apple juice until 1785 by Carl Wilhelm Scheele. Antoine Lavoisier in 1787 proposed the name acide malique which is derived from the Latin word for apple, m?lum, which is the principal flavor that is used in commercial food preparation today.
Essential Metabolism
Malic Acid is formed in metabolic cycles in the cells of plants and animals, including humans. For instance, in both the KREB and glyoxalate cycles it provides the cells with energy and carbon skeletons for the formation of amino acids. A relatively large amount of Malic Acid is produced and broken down in the human body every day. Malic Acid is the principal acid contained in apples and many other fruits and vegetables.
Malic Acid has:
- a clean, mellow, smooth, persistent sourness,
- flavor enhancement and blending abilities,
- a high solubility rate,
- lower hygroscopicity than Citric or Tartaric acids,
- a lower melting point than other acids for easier incorporation into moltenconfections
- good chelating properties with metal ions
It forms:
- economical acidulant blends with other acids,
- more soluble calcium salts than Citric acid, and
- effective buffering mixtures.
Malic Acid in food
Malic Acid contributes to the sourness of green apples. Malic Acid is present in grapes. It confers a tart taste to wine, although the amount decreases with increasing fruit ripeness. The process of malolactic fermentation converts Malic Acid to much milder lactic acid.
Malic Acid, when added to food products, is denoted by E number E296. Malic Acid is the source of extreme tartness in so-called "extreme candy", i.e., Mega Warheads or Sour Punch candies. It is also used with or in place of the less sour citric acid in sour sweets such as Jolly Ranchers, Sweet Tarts and Salt & Vinegar flavor potato chips. These sweets are sometimes labeled with a warning that excessive consumption can cause irritation of the mouth. Malic Acid aids the formulator, because it:
- intensifies the impact of many flavors in foods or beverages, often reducing the amount of flavor needed,
- blends distinct flavors resulting in a well-rounded flavor experience,
- improves aftertaste by extending the impact of some flavors,
- increases burst and aromaticity of some flavor notes in certain beverage applications,
- boosts savory flavors like cheese and hot peppers in snack food coatings, and
- deepens and broadens the flavor profile of many products, resulting in a richer, more natural flavor experience.
Applications using Malic Acid
Carbonated Beverages
Adding Malic Acid improves economies, especially in artificially sweetened products. Flavors are enhanced, allowing the use of less flavor additives, and the overall flavor profile is broader and more natural.
Non-carbonated Beverages
Malic Acid is a preferred acidulant for still beverages (fruit drinks, nectars, iced-teas, sports drinks, calcium fortified juices), because it enhances fruit flavors, improves pH stability, and masks the aftertaste of some salts.
Powdered Mixes
In iced tea, sports drink or fruit soup dry mixes, Malic Acid is preferred due to its rapid dissolution rate and flavor enhancement qualities. Since Malic Acid provides more sourness than Citric acid, less acidulant is required and unit weight can be reduced.
Low Calorie Beverages
In beverages containing intense sweeteners, less Malic Acid than Citric is required to achieve the desired sourness and flavor at a higher pH. Malic Acid's extended sourness masks sweetener aftertaste (see Taste Retention Chart) and its blending and fixative abilities give a balanced taste. In a study with 14-30 year olds, aspartame sweetened low-calorie soft drinks acidified with Malic Acid were preferred over those with Citric acid.
Ciders and Wines
For "alcoholic" apple ciders, Malic Acid is added to maintain a consistent "sharp" taste. In wines, malolactic fermentation improves the flavor profile of the wine.
Acidified "Dairy" Products
- Whey-based protein beverages acidified with Malic Acid have enhanced fruit flavor and less noticeable whey flavor.
- Fruit flavored milk drinks made with fruit juice and acidified with Malic Acid have improved flavor and palatability.
- Coagulated soy-milk acidified with Malic Acid produces a yoghurt-like product.
Calcium Supplements and Calcium-fortified Beverages
In liquid calcium supplements, Malic Acid adds a tart and fruity flavor while controlling the pH. In calcium-fortified beverages, using Malic Acid in place of Citric acid prevents turbidity due to precipitated calcium citrate.
Confectionaries
Malic Acid gives an appealing tartness to hard, soft, tabletted and sugarless candies as well as chewing gum. Blending multiple acids creates unique tasting confections. For example, to prolong the sourness in candy or chewing gum, Citric acid is used for an initial sour boost, Malic Acid for a lingering sourness, and Fumaric acid to sustain the tartness even longer. Malic Acid's high solubility allows it be blended with cooled confections. Adding acids at the end of the candy making process minimizes sugar inversion.
Hard Candy
Malic Acid boosts sourness intensity and enhances fruit flavors. It has a lower melting point than other food acids - this means that it can be incorporated into the molten hard candy without added water - shelf life is increased since the initial moisture level in the hard candy is lower.
Soft Candy
In agar, gelatin or pectin-based candies such as jellies and gummies, Malic Acid is used to achieve a natural fruit flavor profile, proper gelling and good product clarity.
Sugarless Confections
Malic Acid is preferred over Citric acid in this application because it enhances flavor, especially fruit flavors, and boosts sweetness. Blending the sorbitol solution during the heating process is made easier by adding Malic Acid.
Chewing Gum
Organic food acids combined with saccharin improve saliva stimulation in chewing gum. Malic Acid is preferred due to its flavor enhancement properties. Using blends of acids with different partition coefficients results in a sequential release of acid - this creates prolonged juiciness and flavor during chewing.
Fruit Preperations and Preserves
Malic Acid enhances fruit flavors and creates a more natural flavor profile in jams, jellies, and fruit preparations. Malic Acid stabilizes pH to control pectin gel texture due to its strong buffering capacity at the pHs used for pectin gels. Fruit preparations are acidified with Malic Acid so that the fruit flavor stays strong, even when the fruit preparation is used in dairy products, frozen desserts or baked goods.
Desserts
- Fruit preparations for frozen desserts show enhanced fruit flavour when Malic Acid is included
- Malic Acid is an economical fruit flavor enhancer in sherbets and water ices.
- In gelled desserts, Malic Acid enhances fruit flavors and helps stabilize pH to control gel texture.
Bakery Products
Bakery products with fruit fillings (cookies, snack bars, pies, and cakes) have a stronger and more naturally balanced fruit flavor when the fruit filling includes Malic Acid. Pectin gel texture is more consistent due to Malic Acid's buffering capacity.
Medical and Personal Care Products
In throat lozenges, cough syrups, and effervescent powdered preparations, Malic Acid enhances fruit flavor and can diminish the flavor impact of active components. As Malic Acid stimulates saliva flow, it can be used in tooth-cleaning preparations and mouthwashes. Germicidal compounds are used in combination with Malic Acid in soaps, mouthwashes, and toothpaste.
Acid-Based Facial Products
Malic Acid, an alpha hydroxy fruit acid, can be used in skin care products to rejuvenate and improve skin conditions.
Oil Field Applications
Demands for Malic Acid in the oil industry are rapidly increasing. The product is used to aid in the transfer of raw crude from the well to the refinery.
Product Specification - Malic Acid
| Product | DL-Malic Acid, FCC Food Grade |
| Chemical Formula | C4H6O5 |
| Description | Specification |
| Appearance | White Crystalline Granular/ Fine Granular/ Powder |
| Odor | Little or no odor |
| Assay (as DL Malic Acid) on dry basis, wt. % | 99.5 min. |
| Maleic Acid, wt. % | 0.05 max. |
| Fumaric acid, wt. % | 1.0 max. |
| Residue on ignition, wt. % | 0.05 max. |
| Moisture, wt. % | 0.3 max. |
| Color – 10% solution, APHA | 10 max. |
| Heavy Metals (as Pb), ppm | 10 max. |
| Lead (as Pb), ppm | 2 max. |
| Arsenic (as As), ppm | 1 max. |
| Water insoluble matter, wt. % | 0.1 max. |
| Specific Rotation | -0.10° to +0.10° |
Granulations:
| Granular | |
| 100% passing through USS 10 mesh | |
| 10% Max. passing through USS 50 mesh | |
| Fine Granular | |
| 99% Min. passing through USS 25 mesh | |
| 5% Max. passing through USS 100 mesh | |
| Powder | |
| 75% Min. passing through USS 50 mesh | |
Material Safety Data Sheet
| Product Name | DL- Malic Acid |
1. Supplier and Substance Identification
| The Chemical Company | |
| 19 Narragansett Avenue | |
| Jamestown, RI 02835 USA | |
| Phone | 401.423.3100 |
| Fax | 401.423.3102 |
| info@thechemco.com | |
| Web | www.thechemco.com |
| Chemical Name | DL Malic Acid |
| Molecular Formula | C4H6O5 |
| Molecular Weight | 134.09 |
| Synonyms | Hydroxybutanedioic acid, Hydroxysuccinic acid |
2. Composition /Information on ingredients
| Chemical Name | CAS No. | Content (W/W) | EINECS |
| Malic Acid | 617-48-1 | More than 99.5% | 210-514-9 |
| Maleic Acid | 110-16-7 | Less than 0.05% | 203-742-5 |
3. Hazard Identification
| Hazard Symbol | Xi - Irritant |
| R-Phrases | R22, R37/38, R41 |
| S-Phrases | S26, S36 |
4. First Aid Measures
| Inhalation | Remove person from the area of contamination to fresh air. |
| Skin Contact | Wash affected body areas with large volumes of water, if irritation persists, see a physician. |
| Eyes | Flush eyes with clean water, lifting eyelids occasionally, flush with water for 15 minutes. |
| Other | Launder contaminated clothing before re-using. |
5. Fire Fighting Measures
| Flash Point | 245°C |
| Lower Explosion Limit | 16.8 %(V) |
| Upper Explosion Limit | 2.8%(V) |
| Flammable Limits | Not Applicable. |
| Extinguishing Media | Use media that is appropriate to treat surrounding fire. |
| Special Fire Fighting Procedures | Use fire-fighting procedure that is appropriate to treat surrounding fire, all fire fighters should use self-contained breathing apparatus and full fire fighting turnout gear. |
| Unusual fire explosion hazard | Dust can form explosive mixtures with air. |
6. Accidental Release Measures
| Personal precautions | Avoid Inhalation. Use personal protective equipment. Ensure adequate ventilation. |
| Environmental precautions | Remove all sources of ignition. Avoid discharge into environment |
| Methods for cleaning up | Use mechanical handling equipment. Avoid raising dust. Flush with plenty of water. Dispose of incompliance with local and national regulations. |
7. Handling and Storage
| Handling | |
| General advice | Ensure thorough ventilation of stores and work areas. Take precautionary measures against static discharges. Keep away from sources of ignition - No smoking |
| Protection against Fire and explosion | Avoid dust formation. Dust can form an explosive mixture with air. Prevent electrostatic charge - sources of ignition should be kept well clear - fire extinguishers should be kept handy. Electrical devices must meet the specified temperature class. |
| Storage | |
| General advice | Protect against moisture. Containers should be stored tightly sealed in a dry place. |
8. Exposure Controls/Personal Protection
| Engineering Measures | Prevent dust buildup by providing adequate ventilation. |
| Hygiene Measures | Wash hands before consumption of food or drink. |
| Skin and Body | Wear approved protective work boots, work clothing. |
| Hands | Gloves - protective recommended. |
| Eyes | Safety glass with side shields, chemical goggles if contact likely. |
| Hair | Some form of hat or hair covering. |
| Other Devices | Maintain eye wash facility in work area. |
9.Physical and Chemical Properties
| Form | Crystalline Fine granules |
| Colour | White |
| Melting Point ° C | 133 |
| Boiling Point° C | Decomposes at 150 |
| Density g/ml at 20° C | 1.601 |
| Vapor Density (air = 1) | 4.6 |
| Vapor Pressure mmHg at 20° C | <0.1 |
| Flash Point ° C | 245 |
10.Stability and Reactivity
| Stability | Stable at normal temperatures. |
| Conditions to Avoid | Temperatures over 80°C and moisture. |
| Materials to Avoid | Strong oxidants, strong bases, alkali metals, amines, and Carbonates. |
| Decomposition Products | Maleic Acid, Maleic Anhydride, Carbon Monoxide, and Carbon Dioxide. |
11. Toxicological Information
| LD50/oral/mouse | 1600-3200 mg/kg |
| Skin Irritation (Rabbit) | Moderate |
| Eye Irritation (Rabbit) | Severe |
12. Ecological Information
Not Available
13. Disposal Consideration
| Disposal method | |
| Product | To be performed as per local regulations. |
| Contaminated packaging | Can be land filled or incinerated, in compliance with Local Regulations |
14. Transport Information
| DOT Classification | Not a DOT controlled material (United States). |
| Maritime transport IMDG | Not Classified as a dangerous good under transport regulations Air transport ICAO/IATA |
15. Regulatory Information
| INTERNATIONAL REGULATIONS | |
| Listed in EC | 296 |
| Brussels Nomenclature | 2918.19 |
| US Food and Drug Administration | 21 CFR 184.1069 |
Responsibility of the receiver to have the knowledge of the local and national regulations.
16. Other Information
The information provided in this Safety Data Sheet is given in good faith and is correct to the best of our knowledge and information at the date of publication. It is designed only as guidance for safe handling, storage, transportation, use and disposal. No warranty is expressed or implied.
Shipping & Ordering Information
Malic Acid is available for shipping throughout the continental United States with one week lead time for delivery. Please call (401) 423-3100 for details. The product can be delivered in powder form by truck in 1 metric ton (2,204.6 lb) bulk bags, or 25 kg (55.0114 lbs.) bags as well as in liquid solution to our specifications in tanker trucks.
| IUPAC name | hydroxybutanedioic acid |
| Other names | |
| L-Malic Acid | |
| D-Malic Acid | |
| (-)-Malic Acid | |
| (+)-Malic Acid | |
| (S)-Hydroxybutanedioic acid | |
| (R)-Hydroxybutanedioic acid | |
| Identifiers | |
| CAS number | 6915-15-7 Y |
| EC number | 230-022-8 |
| ChemSpider ID | 510 |
| Properties | |
| Molecular formula | C4H6O5 |
| Molar mass | 134.09 g mol-1 |
| Density | 1.609 g/cm³ |
| Melting point | 130 °C |
| Solubility in water | 558 g/l (at 20 °C)[1] |
| Acidity (pKa) | pKa1 = 3.4, pKa2 = 5.13 |
| Related carboxylic acids | |
| propionic acid | |
| butyric acid | |
| succinic acid | |
| tartaric acid | |
| crotonic acid | |
| fumaric acid | |
| pentanoic acid | |
| Related compounds | |
| butanol | |
| butyraldehyde | |
| crotonaldehyde | |
| sodium malate | |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
| Malic Acid is an organic compound with the formula HO2CCH2CHOHCO2H. This dicarboxylic acid is the active ingredient in many sour or tart foods. Malic Acid is found mostly in unripe fruits. | |
| The salts and esters of Malic Acid are known as malates. The malate anion is an intermediate in the citric acid cycle. | |
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