Acidulants fumaric acid

Cda.rhona.tedBeverages. Tartaric acid has been used like citric acid as an acidulant in carbonated beverages (qv). However, it has almost been completely replaced in the marketplace by less expensive acidulants like phosphoric, citric, mafic, and fumaric acids. 

Fumaric acid occurs naturally in many plants and is named after Fumaria officinalis, a climbing aimual plant, from which it was first isolated. It is also known as (E)-2-butenedioic acid, aHomaleic acid, boletic acid, Hchenic acid, or /n j -l,2-ethylenedicarboxylic acid. It is used as a food acidulant and as a raw material in the manufacture of unsaturated polyester resins, quick-setting inks, furniture lacquers, paper sizing chemicals, and aspartic acid [56-84-8]. 

Fumaric acid and malic acid [6915-15-7] are produced from maleic anhydride. The primary use for fumaric acid is in the manufacture of paper siting products (see Papermaking additives). Fumaric acid is also used to acidify food as is malic acid. Malic acid is a particularly desirable acidulant in certain beverage selections, specifically those sweetened with the artificial sweetener aspartame [22839-47-0]. 

Fumaric acid Acidulant, flavoring agent, chelating agent synergist Exhibits synergism when used in combination with other true antioxidants. Low aqueous solubility... 

Fumaric acid is not permitted under UK or EU legislation for direct use in soft drinks, although it is permitted under Annex IV of Directive 95/2/EC (modified by directive 98/72/EC), with strict limits, in instant powders for fruit-, tea- or herbal-based drinks. Fumaric acid finds wide use in other countries as an acidulant, notably in the US market, where it has GRAS ( Generally Recommended As Safe ) status. Fumaric acid is currently manufactured in the United States via the acid-catalysed isomerisation of maleic acid. In terms of equivalent palate acidity it can be used at lower levels than citiic acid and typical replacement is suggested at two parts fumaric acid per three parts citric acid in water, sugar water and carbonated sugar water. 

Producers of acidulants came to food applications through chemistry or biochemistry. Malic acid is produced by Denka, now owned by Mobay, in the United States and by Croda in England. Like fumaric acid, it is a derivative of maleic anhydride production. The... 

Fumaric acid is a naturally occurring sour-tasting compound found in many plants such as Fumaria officinalis L. (Fumariaceae), Boletus scaber Bull. (Boletaceae), and Fames igniaries (Fries) Kickx. (Pluporaceae). It is an essential component for respiration in plant and animal tissues. It is produced by fermentation with mold, such as Rhizopus nigricans, or by chemical synthesis. It is also used in soft drinks and ice cream and as an acidulant along with citric acid. 

Fumaric acid is used primarily in liquid pharmaceutical preparations as an acidulant and flavoring agent. Fumaric acid may be included as the acid part of effervescent tablet formulations, although this use is limited as the compound has an extremely low solubility in water. It is also used as a chelating agent which exhibits synergism when used in combination with other true antioxidants. 

Rhizopus oryzae is an indispensable microorganism in industrial fermentation, as it is widely employed to produce L-lactic acid as well as other organic acids. This organism is able to produce only one stereospecific product (L-lactic acid), rather than a racemic mixture and can, therefore, fulfill the need for producing a food additive to be used as both acidulant and preservative. During L-lactic acid fermentation many other metabolites can be produced as by-products. These include fumaric acid, malic acid, ethanol, and the like. However, these metabolites can greatly influence the downstream process and the quality of the L(+)-lactic acid produced. Fumaric acid is the main by-product, as a result of a special metabolic pathway in L-lactic acid production by R. oryzae (Wang et al., 2005). 

Similar to fumaric acid, L-malic acid is also a naturally occurring four-carbon dicarboxyhc acid and an intermediate in the TCA cycle. It has been used in many food products, primarily as an acidulant. L-Malic acid is compatible with all sugars with low hygroscopicity and good solubihty. In addition, it has therapeutic value for the treatment of hyperammoemia and liver dysfunction and as a component for amino acid infusion. L-Malic acid has been the subject of interest because of its increased application in the food industry as a citric acid replacement and its potential use as a raw material for the manufacture of biodegradable polymers. 

Acidulant use. Acetic, citric and phosphoric acids are the most commonly used acidulants, although lactic, fumaric, adipic, succinic, malic, benzoic, tartaric, ferulic and gluconic acids are sometimes used. Lemon juice, 5% citric acid, and vinegar, 5% acetic acid, are the most commonly used natural acidulants. The acidity of fermented vinegars is often questionable, and should be determined prior to use as an acidifying agent. The acidity of juice from fresh lemons may vary from 4.0 to 8.0% expressed as citric acid, and should also be used carefully. 

Acidification of canned tomatoes with citric, fumaric and malic acids reduced pH effectively (24). Fumaric acid was most effective. Adipic acid was least effective. Succinic acid was an effective acidulant, but induced an undesirable taste. Acidulation tended to reduce pH more when salt was added to tomatoes than when salt was omitted. Acids also tasted less sour in the presence of salts. 

L-aspartic acid ammonia lyase, or aspartase (E.C. 4.3.1.1) is used on a commercial scale by Kyowa Hakko, Mitsubishi, Tanabe and DSM to produce L-aspartic acid, which is used as a building block for the sweetener Aspartame, as a general acidulant and as a chiral building block for synthesis of active ingrediants[1]. The reaction is performed with enzyme preparations from E. coli, Brevibacterium jlavum or other coryneform bacteria either as permeabilized whole cells or as isolated, immobilized enzymes. The process is carried out under an excess of ammonia to drive the reaction equilibrium from fumaric acid (1) in the direction of L-aspartic acid (l-2) (see Scheme 12.6-1) and results in a product of excellent quality (over 99.9% e.e.) at a yield of practically 100%. The process is carried out on a multi-thousand ton scale by the diverse producers of L-aspartic acid. Site directed mutagenesis of aspartase from E. coli by introduction of a Cys430Trp mutation has resulted in significant activation and stabilization of the enzyme P1. 

White Crystals from water, mp 138-139° from alcohol and benzene, mp 130-131°. Faint, acidulous odor characteristic repulsive, astringent taste, d 1.59. Is converted in part into the much higher-melting fumaric acid (mp 287") when heated to a temp slightly above the melting point. Freely sol in water or alcohol. So) in acetone, glacial acetic acid. Slightly sol in ether. Practically insol in benzene. 

Used as non-toxic food acidulent (beverages, baking powders). Fumaric acid esters are used to treat psoriasis. 

Fumaric acid (pkTj = 3.09, p 2 = 4.60 at 25 °C, see Section 8.2.6.1.2) is used as an acidulant and preservative (E297) for inhibition of lactic acid fermentation in wines. Fumaric acid and its esters (especially monomethyl and monoethyl esters) may slow down the formation ofbotulinum toxin formation in canned meat and prevent the growth of moulds in bread. 

Nearly 5% of MA produced in 1978 was converted to fumaric acid. The latter is used in paper sizing resins, specialty unsaturated polyesters, as a food acidulant, and flavoring agent. It has been cleared for use as a special dietary and nutritional additive " and in some indirect applications such as the packaging of food. " " ... 

Fumaric acid Carbon substrate Glucose Rotary biofilm contactor using Rhizopus oryzae 3.78g/L/h Food acidulant and beverage ingredient Myriant Tsao et al. (1999), Jager and Biichs (2012), Guetal. (2013)... 

According to the food laws and regulations of the Food and Drug Administration (FDA), organic acids can be used as acidulants (e.g., citric, fumaric, malic, and sorbic acid), antimicrobial additives (e.g., propionic acid), and sequestrants (e.g., tartaric acid) (14). Most fatty acids of... 

---