Fumaric Acid Overview
Fumaric Acid or trans-butenedioic acid, is a white crystalline chemical compound widely found in nature. Fumaric Acid is a key intermediate in the tricarboxylic acid cycle for organic acid biosynthesis in humans and other mammals. Fumaric Acid is also an essential ingredient in plant life.
Fumaric Acid is found in bolete mushrooms, lichen and Iceland moss. Human skin naturally produces Fumaric Acid when exposed to sunlight. Fumaric Acid is used in the manufacture of medicines, drinks, food, animal feed, cleansing agents, unsaturated polyester, alkyd resins, and printing inks, and is the strongest organic food acid in titratable acidity and sourness.
When used as a food additive, the hydrophobic nature of Fumaric Acid results in persistent, long lasting sourness and flavor impact. The versatile compound also decreases the pH with minimal added sourness in products with pHs greater than 4.5. Its low molecular weight gives Fumaric Acid more buffering capacity than other food acids at pHs near 3.O.
Because of its strength, less Fumaric Acid is required when compared to other organic food acids, therefore reducing costs per unit weight.
About Fumaric Acid
History
Fumaric Acid has been used as a food acidulent since 1946. Fumaric Acid esters were first introduced in the late 1950's by the German chemist Schweckendiek in the treatment of psoriasis. A standardized “Fumaric Acid” protocol for psoriasis was developed and used FAEs both orally and topically. Applications for the chemical compound then expanded to industrial uses.
Fumaric Acid in food
Fumaric Acid is a non-toxic food additive generally used in beverages and baking powders for which requirements are based on purity. It is a substitute for tartaric acid and occasionally takes the place of citric acid, at a rate of 1.36 gram of citric acid to every 0.91 grams of Fumaric Acid for the same taste. It is also an essential ingredient in the manufacturing of candy to add sourness, similar to the way malic acid is used.
Applications using Fumaric Acid
Fumaric Acid has been used in food and beverage products since 1946. It is currently used in wheat and corn tortillas, sour dough and rye breads, refrigerated biscuit doughs, fruit juice and nutraceutical drinks, gelatin desserts, gelling aids, pie fillings and wine. Food research shows that Fumaric Acid improves quality and reduces costs of many food and beverage products. It is also used in animal feed.
Bakery
Tacos
Fumaric Acid lowers the pH of tortilla dough, thereby improving a mold inhibitor's effectiveness. Shelf life of dry tortilla mixes is extended because Fumaric Acid does not absorb moisture during storage and distribution. In wheat flour tortillas, Fumaric Acid accelerates the cleavage of disulphide bonds between gluten protein molecules during dough kneading. The result is more easily machined dough and faster production rates. Added cost savings are realized since leavening acids can be replaced with Fumaric Acid.
Breads
Fumaric Acid acts as an instant flavoring agent for rye and sourdough breads. Fumaric Acid is added to dough ingredients during the dry blending step. Flavor intensity is easily controlled by the amount of Fumaric Acid added to the recipe. In English muffins, Fumaric Acid significantly increases porosity. Dough machinability is improved and more sourness is provided per unit weight.
Beverages
Fruit Juice Drinks
Fumaric Acid provides more sourness per unit weight than other acidulants used in fruit juice drinks. This substantially reduces the acidulant cost. In fruit juice drinks, Fumaric Acid provides more buffering capacity than other acidulants when the pH is near 3.0. Using Fumaric Acid helps to stabilize the pH of a fruit juice drink, which in turn stabilizes color and flavor.
Fumaric Acid in combination with Sodium Benzoate was shown to have a bactericidal effect against E.Coli O157:H7 in apple cider at pHs 3.2-3.4.
Fumaric Acid would help juice processors achieve the mandated 5-log pathogen reduction.
Wine
Fumaric Acid can economically acidify wine with no detectable difference in flavor. The replacement ratio of three pounds of Fumaric Acid to five pounds of Citric acid can significantly reduce acidulant cost. Fumaric Acid also prevents secondary fermentation after bottling and can act as a clarifier when low concentrations of copper and iron are present.
Confectioneries
Fumaric Acid extends the shelf life of acid coated candies because it does not absorb moisture during storage and distribution. Maintaining a low moisture level retards sucrose inversion. Acidulant cost is also reduced as Fumaric Acid provides more sourness per unit weight than other acidulants used in dry form.
Jellies and Jams
Fumaric Acid can cut food acid costs when used as an acidulant for jams, jellies and preserves. As little as two pounds of Fumaric Acid can be used to replace every three pounds of Citric, Malic or Tartaric acid. At the 2:3 replacement ratio, Fumaric Acid does not produce significant differences in gel strength or pH.
Desserts
Alginate Based Desserts
Fumaric Acid is an economical acidulant that liberates calcium. It improves smoothness and optimizes setting times. Also, the non-hygroscopicity of Fumaric Acid means that dry dessert mixes remain free flowing, even in high humidity. Fumaric Acid can be added directly to dry dessert mixes during the manufacturing process without causing degradation of flavor ingredients because of its non-hygroscopic nature.
Gelatin Desserts
Fumaric Acid significantly reduces acidulant costs in gelatin desserts. Depending on the product recipe, each pound of Citric acid can be replaced with 0.6 to 0.7 pounds of Fumaric Acid. Reducing moisture pick-up improves flavor stability and lengthens shelf life. Fumaric Acid maintains non-caking and free-flowing qualities. By keeping the moisture content low, Fumaric Acid helps to maintain the stability of flavor components and markedly decreases inversion of sucrose in the packaged dry mix. It may also be possible to use less expensive packaging if other moisture-sensitive ingredients are not being used in the product formulation. Fumaric Acid also increases gel strength, so food processors may reduce normal gelatin content by about 2%.
Pie Fillings
In pie fillings, Fumaric Acid can be mixed directly with the starch and sugar ingredients, as it is non-hygroscopic. Fumaric Acid lowers costs by reducing the quantity of food acid needed in product formulations. Fumaric Acid also improves smoothness and extends the critical cook times for optimum gelation.
Egg White Foams
Fumaric Acid can promote maximum volume in both egg-white foams and end products based on egg-white foams. Fumaric Acid can replace the more expensive cream of tartar to control egg-white volume. With Fumaric Acid, egg whites can be overbeaten for as much as double the customary optimum time. Well suited for continuous flow processes, Fumaric Acid can be added to both liquid and dried egg whites.
Cleaning Agents for Dentures/Bath Salts
The carbon dioxide generating compounds containing NaHCO3, K2CO3 and powdered Fumaric Acid can be tableted with other ingredients to make cleaning agents for dentures and bath salts.
Animal Feed
Fumaric Acid has proven to be a particularly effective additive to piglet feed during the post-weaning period. The inclusion of Fumaric Acid and the resultant adjustment of the pH value demonstrate improved weight gain, food consumption and feed conversion ratio.
Industrial Uses
Industrial uses of Fumaric Acid include:
- Unsaturated Polyester
- Alkyd Resins
- Printing Inks
- Paper Sizing
Product Specification - Fumaric Acid
| Product | Fumaric Acid, Food Grade |
| Chemical Formula | C4H4O4 |
| Description | Specification |
| Appearance | White Crystalline Powder |
| Odor | None |
| Assay on dry basis, wt. % | 99.5 min. |
| Maleic Acid, wt. % | 0.05 max. |
| Residue on ignition, wt. % | 0.05 max. |
| Moisture, wt. % | 0.3 max. |
| Color – 5% alcohol solution, APHA | 20 max. |
| Heavy Metals (as Pb), ppm | 10 max. |
| Lead (as Pb), ppm 2 max. | |
| Arsenic (as As), ppm | 1 max |
| Solubility in Water @ 30°C, (g/100ml) | 0.7 |
Material Safety Data Sheet
| Product Name | Fumaric 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 | Fumaric Acid |
| Molecular Formula | C4H4O4 |
| Molecular Weight | 116.07 |
| Synonyms | Trans-2-butenedioic acid, (E)-Butenedioic acid, 2-butenedioic acid |
2. Composition /Information on ingredients
| Chemical Name | CAS No. | Content (W/W) | EINECS |
| Fumaric Acid | 110-17-8 | More than 99.5% | 203-743-0 |
| Maleic Acid | 110-16-7 | Less than 0.05% | 203-742-5 |
3. Hazard Identification
| Hazard Symbol | Xi - Irritant |
| R-Phrases | R36 |
| S-Phrases | S2, S26 |
4. First Aid Measures
| Inhalation | Remove the affected individual to fresh air and medical attention required. |
| Skin Contact | Remove contaminated clothing. Wash affected areas thoroughly with soap and water. If irritation develops, seek medical attention. |
| Eyes | In case of contact with the eyes, rinse immediately for at least 15 minutes with plenty of water. Immediate medical attention required. |
5. Fire Fighting Measures
| Explosive Hazard | This material may form flammable dust-air mixtures when finely divided. Prevent dust build-up by providing adequate ventilation. |
| Means of Extinction | Water, carbon dioxide, dry chemicals, wear self-contained breathing apparatus. |
| Hazardous Combustion Products | Toxic fumes of carbon monoxide, carbon dioxide. |
| Protection of Firefighters | Should wear proper protective equipment and self-contained breathing apparatus. |
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
| National Occupational exposure limits | None assigned |
| Engineering measures | Ensure adequate ventilation, well grounded protected electrical equipment. |
| Respiratory | Self contained breathing apparatus |
| Eye | Closely fitted Safety goggles. |
| Hand | Impervious Gloves |
| Skin and body | Approved work boots, protective clothing |
| Hygiene measure | Wash hands during break and at the end of the work |
| Other devices | Maintain eye wash facility in work area |
9.Physical and Chemical Properties
| Form | Power |
| Odor | odorless |
| Color | White |
| Melting Point ° C | 287 |
| Boiling Point ° C | 290 (sublimes) |
| Vapor Pressure mm Hg at 25° C | 1.54 X 10-4 |
| Water Solubility g/l at25° C | 7 |
| Density g/cm³ at 25° C | 1.635 |
10. Stability and Reactivity
| Stability | Stable at normal temperatures. |
| Conditions to Avoid | Temperatures over 190° 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
Acute toxicity (lethal doses)
(Literature value)
| LD50/oral/ rat | 9.3 g/kg |
| LD50/oral/ rat | 1.0 g/kg |
| LD50/dermal/mouse | >20 g/kg |
12. Ecological Information
Biodegradation:
| Toxicity in water | water hazard class 1 (slightly hazardous for water) |
| LC50 (zebra fish) | 245 mg/l(48-h) |
| EC50 (green algae) | 41 mg/l(72-h) |
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 | 297 |
| Brussels Nomenclature | 2917.19 |
| US Food and Drug Administration | 21 CFR 172.350 |
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
Fumaric 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 in various concentrations to our specifications in tanker trucks.
| IUPAC name | (E)-Butenedioic acid |
| Other names | |
| trans-1,2-Ethylenedicarboxylic acid | |
| 2-Butenedioic acid | |
| trans-butenedioic acid | |
| Allomaleic acid | |
| Boletic acid | |
| Donitic acid | |
| Lichenic acid | |
| Identifiers | |
| CAS number | 110-17-8 |
| EC number | 203-743-0 |
| Properties | |
| Molecular formula | C4H4O4 |
| Molar mass | 116.07 g/mol |
| Appearance | White solid |
| Density | 1.635 g/cm³, solid |
| Melting point | 287 °C |
| Solubility in water | 0.63 g/100 mL |
| Acidity (pKa) | pka1 = 3.03, pka2 = 4.44 |
| Hazards | |
| EU classification | Irritant (Xi) |
| R-phrases | R36 |
| S-phrases | (S2) S26 |
| Related carboxylic acids | |
| maleic acid | |
| succinic acid | |
| crotonic acid | |
| Related compounds | |
| fumaryl chloride | |
| fumaronitrile | |
| dimethyl fumarate | |
| iron(II) fumarate | |
©2010 The Chemical Company · The information on this site is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no event shall The Chemical Company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if The Chemical Company has been advised of the possibility of such damages.