Fumaric acid (E297) is an organic compound with antioxidant and anti-inflammatory properties. People use it to treat pain, as a preservative in food, to help prevent cancer, and to treat skin diseases such as psoriasis and eczema. Fumaric acid helps people who have damaged joints or weak bones.
What is fumaric acid?
Fumaric acid is a naturally occurring organic acid that belongs to the alpha hydroxy acid (AHA) family. It is produced by many plants, particularly in the genus Fumaria. It is also produced synthetically and used as a food additive, pharmaceutical ingredient, cosmetic ingredient, and chemical intermediate.
Fumaric acid was first isolated from fumaric acid esters found in beets and other plants.
It has been used for centuries as a food preservative and flavoring agent; it has also been used as a pharmaceutical ingredient to treat conditions such as psoriasis.
Fumaric acid has been shown to improve skin elasticity and reduce fine lines and wrinkles.
What are the natural Sources of fumaric acid?
Fumaric acid is a natural acid found in many fruits and vegetables. It is used as a preservative and flavouring agent, and is also used in the food industry as an emulsifier. Fumaric acid can be obtained from the fruit of several species of fumitory shrub.
Fumaric acid is an organic compound that occurs naturally in many foods, such as apples, almonds, tomatoes, potatoes, grapes and carrots. Fumaric acid is also used as a food additive to provide tartness to foods such as potato chips or soft drinks.
How is fumaric acid made?
The isomerization of maleic acid or glucose fermentation can produce fumaric acid. Two manufacturing processes are described below:
1. Isomerization of Maleic Acid
In this process, maleic acid is heated under pressure in the presence of an acid catalyst. This causes a rearrangement of the carbon atoms in maleic acid, resulting in the formation of a new compound called cis-butenedioic acid. The cis-butenedioic acid can then undergo hydrolysis to give fumaric acid.
2. Sugar fermentation
Fermentation is a technique used to produce organic acids from sugars by using microorganisms such as yeast or bacteria. Fumaric acid can be produced by fermenting sugar under aerobic conditions with Lactobacillus delbrueckii subsp. bulgaricus and Streptococcus thermophilus bacteria.
Specification
| Other Names |
|
| CAS Number | 110-17-8 |
| Chemical formula | C4H4O4 |
| Molecular Weight | 116.072 |
| Melting Point | 287 °C |
| Boiling Point | 156 °C |
Structure
Properties
Appearance
The substance is a white or nearly white crystalline powder or granular powder with a persistent sourness and dryness. The sourness is around 1.5 times that of citric acid.
PKa
Since fumaric acid contains two carboxylic acid functional groups, it has two PKa values. These values are PKa1 = 3.03 and PKa2 = 4.44. The PKa1 and PKa2 values of fumaric acid are higher than those of citrate acid and malic acid.
PH
Fumaric acid is an unsaturated di-carbonic acid that has 2 dissociation equilibrium equations. A concentration of 100 mM (0.1 mol/L) results in a PH value of 2.03.
How to calculate the pH value of fumaric acid?
The pH of fumaric acid is 3.2 to 4.4.
If you want to calculate the pH value of a solution, you must know the concentration of fumaric acid in that solution. In other words, if you have 100 grams of fumaric acid and you want to know its pH value, then you will have to divide the result by 100 grams and multiply it by 10(-2) (or divide it by 100 and multiply it by 10(-2)).
The following example will show you how to calculate the pH value of a solution containing 0.1 grams of fumaric acid:
Solution A: 0.1 g/100 mL = 0.0001 g/mL = 0.1 mmol/L = 1 mmol/L;
Solution B: 1 mmol/L * (10^-2) = 1 x 10^-3 moles per liter;
Solution C: 1 x 10^-3 mol * (6 x 10^-24 kg) / (1 x 10^-3 L) = 6 x 10^21 kg/L;
Solution D: 6 x 10^21 kg / L * (10 moles per kg) / (1000 mL) = 60 mole per 1000 mL.
Solubility
In water
As fumaric acid is hydrophobic, it can disrupt microbial activity by interacting with lipid materials on microbial cell walls.
In organic solvents
Alcoholically soluble, slightly soluble in oils. It is slightly soluble in acetone with a solubility of 1.29g/100g at 20°C.
What are the benefits of fumaric acid?
Fumaric acid is a white, crystalline powder that is used as a food additive and as a medicine. It is also used in the production of polyester resins and some other chemicals.
Because fumaric acid is an organic acid, it can be found in many fruits and vegetables as well as some dairy products.
Fumaric acid has been shown to have several therapeutic uses. It can be used to treat gout, eczema, psoriasis, and other skin conditions when applied topically or taken orally as a solution or capsule. It may also help reduce inflammation and pain associated with rheumatoid arthritis (RA).
Fumaric acid may be useful for treating psoriasis because it inhibits the proliferation of skin cells and reduces hyperproliferation of keratinocytes (skin cells). This helps reduce scaling and flaking of the skin that occurs with this condition. It also seems to reduce itching associated with this condition by suppressing inflammatory cytokines such as IL-17A that are overproduced at sites of inflammation in psoriasis patients.
What is the application of fumaric acid?
The strongest organic food acid is fumaric acid. Due to its hydrophobic characteristics, it is used as both a flavoring agent and an antimicrobial agent. In general, it is used in food, beverage, animal nutrition, cosmetics, and pharmaceutical industries.
Food
- Baking and tortillas: acts as a leavening agent in the leavening agent and as a flavoring agent in savory baked goods.
- Confectionaries and desserts: non-hygroscopic agent.
- Chewing gum: slow dissolution and hydrophobicity prolong the sourness of the gum in the mouth, enhancing its flavor.
Cosmetics
It acts as a buffering agent in cosmetics and personal care products, according to the “European Commission database for information on cosmetic substances and ingredients”.
How safe is fumaric acid to consume?
Fumaric acid is a compound that can be used as a food additive. It is also used as a preservative in foods, cosmetics, pharmaceuticals and more. Fumaric acid is one of the principal products of fermentation of sugar by yeasts (fungi) of the genus Aspergillus.
The Food and Drug Administration (FDA) has approved the use of fumaric acid as an acidulant and flavor enhancer in foods at levels up to 0.6 grams per pound (1.5 grams per kilogram). The European Union has also approved its use in foods.
FDA
Safety
As well as its calcium, ferrous, magnesium, potassium, and sodium salts, fumaric acid can be used in food without compromising safety.
Uses
Besides being an antimicrobial agent, it can also be used as a curing or pickling agent, a flavoring agent or adjuvant, a leavening agent, and a PH control agent.
EFSA
In food
According to Regulation (EU) No 231/2012, fumaric acid (E297) is an authorised food additive that is classified as an “additives other than colours and sweeteners”.
Uses
Here are some foods that may contain E297 at its maximum level:
| Food Category | Maximum Level |
| Fruit-flavoured desserts | 4000 |
| Sugar confectionery | 1000 |
| Chewing gum | 2000 |
| Decorations, coatings and fillings | 1000 |
| Fillings and toppings for fine bakery ware | 2500 |
| Instant products for preparation of flavoured tea and herbal infusions | 1000 |
| Gel-like desserts, fruit-flavoured desserts, dry powdered dessert mixes | 1000 |
In feed
All animal species are currently allowed to consume fumaric acid as a preservative in their feed. As long as an expected use level of 20 000 mg/kg in complete diets for pigs and poultry is not exceeded, it is considered safe for use.
UK Food Standards Agency
This item is categorized as “Others”
Food Standards Australia New Zealand
Australia and New Zealand have approved it under the code number 297.
JECFA
Function class: food additive, flavouring agent and acidity regulator.
Acceptable daily intake: The 1999 safety re-evaluation found that ADI “not specific” was set in 1989 and that current intake levels were not unsafe.
What is the side effects of fumaric acid?
Many consumers wonder whether fumaric acid is harmful to our health and what the possible health risks are. We understand that consumers prefer natural ingredients and are concerned about synthetic acidity regulators in food. There are some people who may be allergic or sensitive to it, but it is generally considered safe.
Allergy
There have been few reports regarding its side effects, but some allergic people may experience headaches, diarrhea, nausea, and other symptoms.
Is it Safe for Pregnant?
It is generally safe, but you should consult your doctor before using it.
What is fumaric acid derived from?
Fumaric acid is a white crystalline compound with a slight acid taste. It is soluble in water and ethanol, but not in ether. Fumaric acid is produced by the fermentation of glucose by certain fungi, such as Rhizopus oryzae, and by some bacteria, e.g., Pseudomonas putida.
Fumaric acid is an intermediate in the metabolism of carbohydrates and proteins. It occurs naturally in many foods, including apples, apricots, broccoli, Brussels sprouts, cabbage, cauliflower, cucumbers, grapefruit juice and wine, lentils and peas.
Fumaric acid is used as a preservative in food products such as salad dressings and tomato juice; as a stabilizer for some cosmetics; and to control pH levels in pharmaceuticals or food additives such as chewing gum bases or toothpaste bases (e.g., xylitol).
How polar is fumaric acid?
Fumaric acid is a polar organic compound with the chemical formula HCOOH. The pure acid is colorless and can be made by oxidizing maleic acid. Fumaric acid is used as an additive in foods, beverages, pharmaceuticals, personal care products and cosmetics.
Fumaric acid is produced commercially by the reaction of maleic anhydride with carbon monoxide or propylene using a palladium catalyst.
Is fumaric acid a solid liquid or gas?
Fumaric acid is a carboxylic acid. The equilibrium between the solid and liquid phases depends on temperature, pressure and concentration. At 25°C, fumaric acid exists as a solid at all concentrations above 0.01M (0.1%). At temperatures below 25°C, fumaric acid exists as a solid at all concentrations above 0.1% (10 g/L).
Fumaric acid exhibits polymorphism: one form melts at about 150°C; another melts at about 190°C. Each form has a different density, so they can be separated by density difference using analytical techniques like centrifugation or filtration.
Is fumaric acid organic or inorganic?
Fumaric acid is a naturally occurring organic compound found in many plants and animals. The fumaric acid that is used in the food industry, however, is synthetic and manufactured in a laboratory.
The organic form of fumaric acid is found in many fruits and vegetables such as apples, tomatoes, carrots, squash and spinach. It can also be found in animal products like eggs and dairy products. Fumaric acid can be extracted from these foods through fermentation or by using distillation methods to isolate the acid from its natural source.
Fumaric acid is used as a food additive to give foods a tart flavor and it can also be used as an antioxidant preservative for some types of cheeses such as Swiss cheese. It is also used as an acidulant for beverages including soft drinks, fruit juices and wine coolers.
Is fumaric acid soluble or insoluble?
Fumaric acid is a carboxylic acid. It exists as a white crystalline powder at room temperature.
Fumaric acid is soluble in water, but it can also be dissolved in alcohols, glycols, and other organic solvents.
There are no dangers associated with fumaric acid, though it may cause skin irritation if not handled properly.
Fumaric acid is produced by which fungi?
Fumaric acid is produced by many species of fungi. The most notable are the genus Fusarium and its teleomorphic (sexual) stage, Verticillium. Fusarium oxysporum is the most common cause of seedling blight in beans, peas and other legumes. It also infects onions, leeks, chrysanthemums and many other crops.
Where to buy fumaric acid?
Fumaric acid can be purchased from various online stores like Amazon and eBay. You can also find it at local pharmacies and grocery stores.
The following are some of the best places to buy fumaric acid:
Amzon: Amazon offers a wide range of products including food items, beauty products, clothing and accessories etc. In addition to this, you will get great deals on all products available at Amazon.
Ebay: ebay has been around for over 20 years now and continues to grow with each passing day. The site offers all kinds of products including electronics, clothes, footwear etc., making it easy for you to find whatever it is that you want without having to run around different shops looking for it!
Frequently Asked Questions
Is it Natural?
Fumaric acid is a natural acid, found in food and the human body. It’s commonly used as an additive to foods like yogurt, ice cream and beverages. Fumaric acid is also used in skin care products and sunscreens to help prevent aging, wrinkles and dark spots.
Fumaric acid is a substance that naturally occurs in many plants, especially in berries. It was first isolated from fumitory root (Fumaria officinalis), a plant that has been used medicinally for hundreds of years.
Is it Vegan?
Fumaric acid is a natural preservative that is approved by the FDA for use in food products. It is also used as a pharmaceutical drug to treat various conditions such as psoriasis and Crohn’s disease.
Fumaric acid is not considered vegan because it contains gelatin, which comes from animal bones. However, fumaric acid is derived from beets, so some vegans do consider it to be vegan-friendly.
It’s important to note that some companies may use animal-derived ingredients when producing fumaric acid, so you should always check with them before purchasing or using their product.
Is it Halal?
Fumaric acid is a natural organic acid that is widely used in food and beverage industry as a flavoring agent. It is also used as a food additive in the form of its sodium salt, sodium fumarate to improve the flavor of baked goods. Fumaric acid is naturally present in many foods including fruit, wine, cheese and yogurt.
Fumaric acid is produced from amino acids found in wafers, cookies and other products. It’s also found in some breads. Fumaric acid occurs naturally in some fruits, vegetables and animal products such as milk and eggs.
Fumaric acid is Halal if it’s from vegetable sources only (e.g., corn syrup) or from Halal animal sources only (e.g., gelatin).
Is it Kosher?
Fumaric acid is a naturally occurring organic acid that is used in the food and cosmetic industry as a food additive. It can also be found in some pharmaceutical drugs.
Fumaric acid is approved for use in foods by the FDA and Health Canada, and it’s considered safe for human consumption at levels of less than 5 milligrams per kilogram of bodyweight per day. Fumaric acid is not known to cause allergic reactions in humans or animals, but it may have undesirable effects on some people who suffer from kidney disease or liver disease.
The Kosher symbol on products containing fumaric acid indicates that they are certified as kosher by the Orthodox Union, an organization that certifies products produced according to Jewish law.
Is it Gluten free?
Yes, fumaric acid is gluten free. Fumaric acid can be found in the following foods:
Cereals and cereal products
Cereal grains are commonly used in the manufacture of prepared foods. The Food and Drug Administration (FDA) has established a guideline for manufacturers to determine if a food contains less than 20 parts per million (ppm) of gluten. Gluten can also be found in foods that are not made with wheat, barley, or rye such as rice cakes, potato chips, tortilla chips, popcorn, and pretzels.
Fruits and vegetables
Fruits and vegetables are naturally gluten-free. The FDA has established a guideline for manufacturers to determine if a food contains less than 20 ppm of gluten.
What is Fumarate?
Fumarate is an organic compound with the formula CH2O2. It is a derivative of fumaric acid, in which both carboxyl groups have been converted to hydroxyl groups.
Fumaric acid was first isolated in 1822 by German chemist Johann Gottlob Leuckart by adding sulfuric acid to succinic acid. Fumaric acid is sometimes called dihydrophthalic acid.
Fumaric acid and its derivatives are used as food additives and solvents. They are also used as antifungal agents in soaps and disinfectants, for instance in some mouthwashes, toothpastes and shampoos to prevent fungal growth on contact lenses.
Conclusion
Drugs like fumaric acid are considered as food additives and, thus, it is important to ensure that the presence of fumaric acid additives in packaged food products and beverages will not pose a threat to consumers since they are generally recognized as safe food substances. So while fumaric acid is thought to be safe and ingesting them is not likely to cause a problem, more research still needs to be done on whether or not their beneficial effects should be incorporated into daily diets.
