AMBER ACID
Amber acid is a dicarboxylic acid with the chemical formula (CH₂)₂(CO₂H)₂, naturally found in living organisms and acting as a key metabolic intermediate in the citric acid cycle.
Bio-based Amber acid is seen as an important platform chemical for the production of biodegradable plastics and as a substitute for several petrochemical-derived chemicals such as adipic acid.
Amber acid links cellular metabolism, especially ATP formation, to the regulation of cellular function, and its dysregulation can contribute to mitochondrial diseases and pathological conditions like inflammation and tissue injury.
CAS Number: 110-15-6
EC Number: 203-740-4
Chemical Formula: HOOCCH₂CH₂COOH
Molar Mass: 118.09 g/mol
Synonyms: Acido succinico, Succinic acid, C4-beta-polymorph, STR02803, Amber acid, Ammonium succinate, Sal succini, Acide succinique, Ethanedicarboxylic acid, Succinic acid (8CI), 1cze, Kyselina jantarova, 1,2-Ethanedicarboxylic acid, Butane diacid, Butanedioic acid, SuccinicAcid(IndustrialGrade&FoodGrade), 1,4-Butanedioate, Nat.Succinic Acid, Bernsteinsaeure, succ, succinate, Spirit of amber, Acide butanedioique, Acidum succinicum, Succinicate, Ethylene succinic acid, HOOC-CH2-CH2-COOH, Butanedionic acid, Acid of amber, Wormwood acid, DSSTox_CID_3602, 110-15-6, 4-02-00-01908, 203-740-4, AI3-06297, Bernsteinsaure, Succ, Dihydrofumarate, AB6MNQ6J6L, DTXSID6023602, Substrate analogue, 9, Dihydrofumaric acid, WLN: QV2VQ, AB01332192-02, ZINC895030, s3791, MCULE-5889111640, BMSE000968, BMSE000183, BDBM26121, DB00139, Ethylene dicarboxylic acid, Bernsteinsäure, GTPL3637, 26776-24-9, acide succinique, succinic-acid, Butanedioic acid, 1,4-Butanedioic acid, EINECS 203-740-4, FEMA NO. 4719, GTPL3637, Bernsteinsaeure, acide butanedioique, acido succínico, ácido succínico, ácido succínico, AI3-06297, NCGC00257092-01, NCGC00259467-01, NCGC00159372-02, NCGC00159372-03, NCGC00159372-04, NCGC00159372-05, NCGC00159372-06, Succinellite, Succinic acid, FCC, Succinic acid, FCC, FG, Succinic acid, natural, Succinic acid, BioXtra, >=99.0%, Succinic acid, ACS grade, Succinic acid, >=99%, FT-0652509, FT-0773657, BP-21128, I847, A14596, HY-N0420, 1,2-Ethanedicarboxylate, LS40373, MCULE-5889111640, Q213050, SR-01000944556, SR-01000944556-2, Z57127453, BBL002473, Tox21_111612, Tox21_201918, Tox21_303247, Tox21_111612_1, CCG-266069, HMS3885O04, N1941, S0100, 6, 37E8FFFB-70DA-4399-B724-476BD8715EF0, C00042, D85169, J-002386, DB00139, D85169, AI3-06297, AI3-06297, 4lh2, 1,4-Butanedioic acid, 1,4-Butandioic Acid, acide succinique, succinic acid (free acid), succunic acide, Succinic acid, puriss. p.a., ACS reagent, >=99.5% (T), Succinic acid, certified reference material, TraceCERT(R), Ultra pure, HOOC-CH2-CH2-COOH, Succinic acid, United States Pharmacopeia (USP) Reference Standard, Succinic acid, matrix substance for MALDI-MS, >=99.5% (T), Succinic acid, Pharmaceutical Secondary Standard; Certified Reference Material, Succinic acid, SAJ first grade, >=99.0%, Succinic acid, p.a., ACS reagent, 99.0%, Succinic acid, SAJ special grade, >=99.5%, Succinic acid, anhydrous, free-flowing, Redi-Dri(TM), ACS reagent, >=99.0%, Succinic acid, BioReagent, suitable for cell culture, suitable for insect cell culture, Butanedioic acid?, NCGC00159372-02, 4-02-00-01908, CHEBI:15741, MFCD00002789, MFCD00002789, Ethanedicarboxylic acid, CAS-110-15-6, acide succinique, DTXSID6023602, WLN: QV2VQ, Dihydrofumaric acid, Acidum succinicum, Spirit of amber, Succinic acid (SA), succinic-acid, Amber acid, 1,2-Ethanedicarboxylic acid, 1,4-Butanedioic acid, Bernsteinsäure, acide succinique, acidum succinicum, Янтарная кислота, 14493-42-6, 152556-05-3, 21668-90-6, 61128-08-3, Sal succini, Butandisaeure, BUTANE DIACID, BUTANEDIOICACID, FMR, fum, hydron, Katasuccin, Kyselina jantarova, MAE, Maleic acid, Acide butanedioique, Bernsteinsaeure, Succinellite, Succinic acid, AI3-06297, STR02803.
Amber acid is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2.
The name derives from Latin succinum, meaning amber.
In living organisms, Amber acid takes the form of an anion, which has multiple biological roles as a metabolic intermediate being converted into fumarate by the enzyme succinate dehydrogenase in complex 2 of the electron transport chain which is involved in making ATP, and as a signaling molecule reflecting the cellular metabolic state.
Amber acid is marketed as food additive E363.
Amber acid is generated in mitochondria via the tricarboxylic acid cycle (TCA).
Amber acid can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating epigenetic landscape or demonstrating hormone-like signaling.
As such, Amber acid links cellular metabolism, especially ATP formation, to the regulation of cellular function.
Dysregulation of Amber acid synthesis, and therefore ATP synthesis, happens in some genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome, and degradation can lead to pathological conditions, such as malignant transformation, inflammation and tissue injury.
Amber acid, a four-carbon diacid, has been the focus of many research projects aimed at developing more economically viable methods of fermenting sugar-containing natural materials.
Amber acid fermentation processes also consume CO2, thereby potentially contributing to reductions in CO2 emissions.
Amber acid could also become a commodity used as an intermediate in the chemical synthesis and manufacture of synthetic resins and biodegradable polymers.
Much attention has been given recently to the use of microorganisms to produce Amber acid as an alternative to chemical synthesis.
We have attempted to maximize Amber acid production by Actinobacillus succinogenes using an experimental design methodology for optimizing the concentrations of the medium components.
The first experiment consisted of a 24−1 fractional factorial design, and the second entailed a Central Composite Rotational Design so as to achieve optimal conditions.
Under the best conversion conditions, as determined by statistical analysis, the production of Amber acid was carried out in an instrumented bioreactor using sugarcane bagasse hemicellulose hydrolysate, yielding a concentration of 22.5 g l−1.
Amber acid is a precursor of many important, large-volume industrial chemicals and consumer products.
Amber acidwas once common knowledge that many ruminant microorganisms accumulated Amber acid under anaerobic conditions.
However, Amber acid was not until the discovery of Anaerobiospirillum succiniciproducens at the Michigan Biotechnology Institute (MBI), which was capable of producing Amber acid up to about 50 g/L under optimum conditions, that the commercial feasibility of producing the compound by biological processes was realized.
Other microbial strains capable of producing Amber acid to high final concentrations subsequently were isolated and engineered, followed by development of fermentation processes for their uses.
Processes for recovery and purification of Amber acid from fermentation broths were simultaneously established along with new applications of Amber acid, e.g., production of biodegradable deicing compounds and solvents.
Several technologies for the fermentation-based production of Amber acid and the subsequent conversion to useful products are currently commercialized.
This review gives a summary of the development of microbial strains, their fermentation, and the importance of the down-stream recovery and purification efforts to suit various applications in the context of their current commercialization status for biologically derived Amber acid
Amber acid, with molecular formulation C4H6O4, is a water-soluble, odorless, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters.
Amber acid is also used in foods as a sequestrant, buffer, and a neutralizing agent.
Amber acid is a normal intermediary metabolite and a constituent of the citric acid cycle, and found naturally in human urine
Amber acid is distributed widely through the natural world, where Amber acid is contained in bivalves, fossils, seaweed, lichen, bacteria and so on.
Amber acid was discovered in the year 1550 when Dr. Agricola with Germany distilled amber.
Amber acid is useful, non-toxic, stable and harmless to the human body.
Amber acid is generated in a citric acid cycle (Amber acid dehydrate enzyme) and a Amber acid-glycine cycle through the process of metabolism and eventually becomes energy.
Amber acid is industrially produced by hydrogenation of Maleic Anhydride.
Amber acid of NIPPON SHOKUBAI has not only been used as food additives but also biodegradable polymers, bath additives, plating agents, photochemicals and so on
Amber acid is a precursor of many important, large-volume industrial chemicals and consumer products.
Amber acid was once common knowledge that many ruminant microorganisms accumulated Amber acid under anaerobic conditions.
However, Amber acid was not until the discovery of Anaerobiospirillum succiniciproducens at the Michigan Biotechnology Institute (MBI), which was capable of producing Amber acid up to about 50 g/L under optimum conditions, that the commercial feasibility of producing the compound by biological processes was realized.
Other microbial strains capable of producing Amber acid to high final concentrations subsequently were isolated and engineered, followed by development of fermentation processes for their uses.
Processes for recovery and purification of Amber acid from fermentation broths were simultaneously established along with new applications of Amber acid, e.g., production of biodegradable deicing compounds and solvents.
Several technologies for the fermentation-based production of Amber acid and the subsequent conversion to useful products are currently commercialized.
This review gives a summary of the development of microbial strains, their fermentation, and the importance of the down-stream recovery and purification efforts to suit various applications in the context of their current commercialization status for biologically derived Amber acid.
Amber acid is an alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group.
Amber acid is an intermediate metabolite in the citric acid cycle.
Amber acid has a role as a nutraceutical, a radiation protective agent, an anti-ulcer drug, a micronutrient and a fundamental metabolite.
Amber acid is an alpha,omega-dicarboxylic acid, a C4-dicarboxylic acid and a lipid.
Amber acid accounts for up to the 90% of the nonvolatile acids produced during alcoholic fermentation.
The content of this acid in wine ranges normally from 0.5 to 1.5 g/L, but the maximum concentration may reach 3 g/L.
Amber acid is a diprotic acid.
Amber acid pKa at 25°C are 4.21 and 5.64.
This means that at pH 3.50, most Amber acid (83.9%) is present in Amber acid undissociated form; monodissociated Amber acid ion accounts only for approximately 16%, while the dissociation of the second carboxylic group is practically negligible
Amber acid, an organic acid is an important building block that has a wide range of synthetic applications.
Presently Amber acid is synthesized from petrochemical compounds.
Due to Amber acid increasing demand many bio-based methods have been proposed for Amber acid synthesis as an efficient alternative.
Amber acids utility as a low shrinkage additive (LSA) in unsaturated polyester resin (UPR) has been investigated.
Amber acid (COOH(CH2)2COOH) is a carboxylic acid used in food (as an acidulant), pharmaceutical (as anexcipient), personal care (soaps) and chemical (pesticides, dyes and lacquers) industries.
Bio-based Amber acid is seen as an important platform chemical for the production of biodegradable plastics and as a substitute of several chemicals (such as adipic acid)
Amber acid was traditionally produced synthetically from fossil oil or by an expensive distillation of amber.
During the last decade, new methods of production through biotechnological processes have been developed industrially (so-called bio-Amber acid).
Looking for more natural ingredients, the cosmetics market now has access to a new affordable plant-based ingredient.
Amber acid is an aliphatic dicarboxylic acid (diacid) described by the empirical formula C4H6O4, and is naturally found in living organisms.
This diacid is one entry pathway into the Krebs cycle that takes place inside the mitochondria found in all cells in the human body.
Amber acid provides energy required for the organism to function and is therefore involved in a variety of important biological actions.
Widely used in the food industry as a chelating agent and as a pH adjuster, Amber acid has been recognized as a safe substance for years.
Amber acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.
Amber acid is used by consumers, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Amber acid a dicarboxylic acid of molecular formula C4H6O4 that is widely distributed in almost all plant and animal tissues and that plays a significant role in intermediary metabolism.
Amber acid is a colourless crystalline solid, soluble in water, with a melting point of 185–187° C (365–369° F).
Amber acid is a precursor to some polyesters and a component of some alkyd resins.
Amber acid) can be synthesized using Amber acid as a precursor.
The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams.
Amber acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications.
Acylation with Amber acid is called succination.
Oversuccination occurs when more than one Amber acid adds to a substrate
As a food additive and dietary supplement, Amber acid is generally recognized as safe by the U.S. Food and Drug Administration.
Amber acid is used primarily as an acidity regulator in the food and beverage industry.
Amber acid is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste.
As an excipient in pharmaceutical products, Amber acid is also used to control acidity or as a counter ion.
Amber acid is found in all plant and animal materials as a result of the central metabolic role played by this dicarboxylic acid in the Citric Acid Cycle.
Amber acid concentrations are monitored in the manufacture of numerous foodstuffs and beverages, including wine, soy sauce, soy bean flour, fruit juice and dairy products (e.g. cheese).
Amber acid is a dicarboxylic acid.
Amber acid is a common intermediate in the metabolic pathway of several anaerobic and facultative micro-organisms.
Amber acid is used as a dietary supplement for symptoms related to menopause such as hot flashes and irritability.
Amber acid is used as a flavoring agent for food and beverages.
Amber acid is used to manufacture polyurethanes, paints and coatings, adhesives, sealants, artificial leathers, cosmetics and personal care products, biodegradable plastics, nylons, industrial lubricants, phthalate-free plasticizers, and dyes & pigments.
In the pharmaceutical industry, Amber acid is used in the preparation of active calcium succinate, as a starting material for active pharmaceutical ingredients (adipic acid, N-methyl pyrrolidinone, 2-pyrrolidinone, succinate salts, etc.), as an additive in drug formation, for medicines of sedative, antispasmer, antiplegm, antiphogistic, anrhoter, contraception and cancer curing, in the preparation of vitamin A and anti-Inflammatory, and as antidote for toxic substance.
Amber acid is a naturally occurring dicarboxylic acid with the molecular formula C4H6O4.
Amber acid consists of a four-carbon chain with two carboxylic acid groups located at each end.
Structurally, Amber acid is one of the simplest dicarboxylic acids.
In its pure form, Amber acid appears as a colorless, odorless crystalline solid that is soluble in water and slightly soluble in alcohols and ether.
Amber acid's aqueous solutions exhibit weak acidity due to the partial ionization of its carboxyl groups.
Biologically, Amber acid plays a critical role in cellular metabolism as an intermediate in the citric acid cycle (Krebs cycle), which is essential for the production of cellular energy in aerobic organisms.
Amber acid is produced naturally by both plants and animals and can also be synthesized by certain bacterial fermentation processes.
Historically, Amber acid was first isolated from amber, which is reflected in its name.
Nowadays, Amber acid is commonly produced through bio-based fermentation methods using renewable feedstocks, making it an important building block in sustainable chemical manufacturing.
Amber acid is widely valued for its versatility and functionality across multiple industries.
Amber acid serves as a precursor for the synthesis of numerous chemicals such as 1,4-butanediol, tetrahydrofuran (THF), and gamma-butyrolactone (GBL).
Amber acid is also used in food as an acidity regulator and flavor enhancer, in pharmaceuticals as an excipient or intermediate, and in biodegradable plastics, resins, solvents, and personal care products.
The molecule's two carboxyl groups allow Amber acid to undergo a variety of chemical reactions including esterification, amidation, and polymerization, making it highly adaptable in industrial chemistry.
With the rising emphasis on green chemistry and sustainable production, bio-based Amber acid has gained increasing importance in recent years.
Applications of Amber Acid:
Amber acid is used to make lacquers, dyes, esters for perfumes, alkyd resins, pharmaceuticals, plasticizers, lubricants, and pesticides.
Amber acid is also used in photography, as a sequestrant in foods, a buffering and neutralizing agent, for radiation dosimetry, and to promote plant growth and increased yields in food crops.
Amber acid (COOH(CH2)2COOH) is a carboxylic acid used in food (as an acidulant), pharmaceutical (as an excipient), personal care (soaps) and chemical (pesticides, dyes and lacquers) industries.
Bio-based Amber acid is seen as an important platform chemical for the production of biodegradable plastics and as a substitute of several chemicals (such as adipic acid).
Amber acid is widely used in the food industry as a chelating agent and as a pH adjuster.
The FDA has granted Amber acid with the GRAS status (Generally Recognised as Safe Substance).
Studies conducted within the food industry show Amber acid has anti-oxidant properties: even though this does not imply the same will be exerted when Amber acid is applied topically, Amber acid gives an indication that suitable tests could be carried out to understand whether Amber acid maintain such effect once formulated in a cosmetic product.
Amber acid is also used as an intermediate to manufacture several chemicals, amongst which raw materials for the cosmetic and personal-care industry, e.g. emollients, surfactants and emulsifiers.
Amber acid is widely use as organic intermediates for the pharmaceutical, engineering plastics, resins etc.
For the synthesis of sedatives, contraceptives and cancer drugs in the pharmaceutical industry.
In the chemical industry for the production of dyes, alkyd resin, glass fiber reinforced plastics, ion exchange resins and pesticides.
Amber acid is an acidulant that is commercially prepared by the hydrogenation of maleic or fumaric acid.
Amber acid is a nonhygroscopic acid but is more soluble in 25°c water than fumaric and adipic acid.
Amber acid has low acid strength and slow taste build-up; Amber acid is not a substitute for normal acidulants.
Amber acid combines with proteins in modifying the plasticity of bread dough.
Amber acid functions as an acidulant and flavor enhancer in relishes, beverages, and hot sausages.
Biotechnological Applications:
Amber acid and its derivatives are used as flavoring agents for food and beverages.
This acid could be used as feedstock for dyes, insecticides, perfumes, lacquers, as well as in the manufacture of clothing, paint, links, and fibers.
Amber acid is widely used in medicine as an antistress, antihypoxic, and immunity-improving agent, in animal diets, and as a stimulator of plant growth.
Amber acid is also a component of bio-based polymers such as nylons or polyesters.
Amber acid esters are precursors for the known petrochemical products such as 1,4-butanediol, tetrahydrofuran, c-butyrolactone, and various pyrrolidinone derivatives.
Amber acid production was reported for the first time when Amber acid was grown on ethanol under aerobic conditions and nitrogen limitation.
Amber acid amount was 63.4 g/L as the major product of batch fermentation in this process.
However, the disadvantage was low yield of Amber acid on ethanol (58 %), and a high cost of production.
The concentration of Amber acid and Amber acid yield were found to be 38.8 g/L and 82.45 % of n-alkane consumed, respectively.
Amber acid production was also studied by genetically modified strains using glucose and glycerol as substrates.
Constructed temperaturesensitive mutant strains with mutations in the Amber acid dehydrogenase encoding gene SDH1 by in vitro mutagenesis-based approach.
Then, the mutants were used to optimize the composition of the media for selection of transformants with the deletion in the SDH2 gene.
The defects of each Amber acid dehydrogenase subunit prevented the growth on glucose, but the mutant strains grew on glycerol and produced Amber acid in the presence of the buffering agent CaCO3.
Subsequent selection of the strain with deleted SDH2 gene for increased viability was allowed to obtain a strain that is capable to accumulate Amber acid at the level of more than 450 g/L with buffering and more than 17 g/L without buffering.
Therefore, a reduced Amber acid dehydrogenase activity can lead to an increased Amber acid production
Uses of Amber Acid:
Amber acid has a wide range of uses across various industries due to its versatility and biocompatibility.
In the chemical industry, Amber acid serves as an important precursor for producing compounds such as 1,4-butanediol, tetrahydrofuran (THF), and gamma-butyrolactone (GBL), and is a key monomer for manufacturing biodegradable polymers like polybutylene succinate (PBS).
In the pharmaceutical sector, Amber acid is used as an intermediate in drug synthesis and is studied for its potential anti-inflammatory, antioxidant, and energy-boosting properties.
In the food and beverage industry, Amber acid functions as a food additive, acting as an acidity regulator and flavor enhancer, imparting a mild sour taste to foods and drinks.
Amber acid also finds applications in agriculture as a plant growth promoter and soil conditioner, and in cosmetics and personal care products where it helps regulate pH and enhance skin hydration.
Additionally, Amber acid is explored in biomedical fields for tissue engineering and drug delivery systems due to its biodegradability.
Environmentally, Amber acid plays a crucial role in green chemistry as a building block for bio-based products, offering sustainable alternatives to petroleum-derived chemicals.
Amber acid is also used in textile and leather processing for pH control and in industrial formulations as a component of solvents and cleaning agents.
Chemical Industry:
As a precursor for manufacturing other chemicals like 1,4-butanediol (BDO), tetrahydrofuran (THF), and gamma-butyrolactone (GBL).
In the production of biodegradable polymers such as polybutylene succinate (PBS), which is used for making environmentally friendly plastics.
Pharmaceutical Industry:
Amber acid is used as a pharmaceutical intermediate for synthesizing active ingredients and excipients.
Sometimes employed as an anti-inflammatory agent, antioxidant, and in treatments to improve energy metabolism.
Component in some anesthetic and sedative formulations.
Food and Beverage Industry:
Amber acid functions as a food additive, serving as an acidity regulator, flavor enhancer, and preservative.
Amber acid adds a mild, sour, umami-like flavor to beverages, candies, and processed foods.
Agriculture:
Utilized in plant growth enhancement and soil conditioners.
Amber acid sometimes incorporated into fertilizer formulations to promote plant vigor and resilience.
Cosmetic and Personal Care Products:
Incorporated into skin care formulations due to Amber acid's pH-regulating and moisturizing properties.
Amber acid is used in soaps, creams, lotions, and facial masks to improve skin texture and appearance.
Biomedical Applications:
Research interest in biomedical scaffolds and tissue engineering because of Amber acid's biocompatibility and degradability.
Studied for use in drug delivery systems.
Environmental and Green Chemistry:
Amber acid acts as a building block for the development of bio-based and renewable chemicals.
Important in producing sustainable alternatives to petrochemical-based products.
Textile and Leather Industry:
Amber acid is used in the dyeing and finishing processes of textiles and leather as a buffering agent and pH controller.
Industrial Solvents:
Amber acid serves as a base for making solvents used in cleaning products and manufacturing processes.
Consumer Uses:
Amber acid is used in the following products: adsorbents, fertilisers, inks and toners, washing & cleaning products, water softeners, adhesives and sealants, coating products, fillers, putties, plasters, modelling clay, perfumes and fragrances, pharmaceuticals, polymers and cosmetics and personal care products.
Other release to the environment of Amber acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
Widespread uses by professional workers:
Amber acid is used in the following products: pH regulators and water treatment products, anti-freeze products, metal surface treatment products, heat transfer fluids, hydraulic fluids, washing & cleaning products, fertilisers, water softeners and cosmetics and personal care products.
Amber acid is used in the following areas: printing and recorded media reproduction, health services and scientific research and development.
Amber acid is used for the manufacture of: and plastic products.
Other release to the environment of Amber acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use and outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids).
Uses at industrial sites:
Amber acid is used in the following products: pH regulators and water treatment products, metal surface treatment products, leather treatment products, metal working fluids and laboratory chemicals.
Amber acid is used in the following areas: municipal supply (e.g. electricity, steam, gas, water) and sewage treatment and scientific research and development.
Amber acid is used for the manufacture of: chemicals, plastic products and textile, leather or fur.
Release to the environment of Amber acid can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture, in the production of articles and as processing aid.
Chemical Properties of Amber Acid:
Amber acid is a normal constituent of almost all plant and animal tissues.
Succinic anhydride is the dehydration product of the acid.
Amber acid was first obtained as the distillate from amber (Latin, Succinum) for which Amber acid is named.
Amber acid occurs in beet, brocoli, rhubarb, sauerkraut, cheese, meat, molasses, eggs, peat, coal, fruits, honey, and urine.
Amber acid is formed by the chemical and biochemical oxidation of fats, by alcoholic fermentation of sugar, and in numerous catalyzed oxidation processes.
Amber acid is also a major byproduct in the manufacture of adipic acid.
Amber acid, a dicarboxylic acid, is a relatively new nonhygroscopic product approved for food uses.
Amber acid apparent taste characteristics in foods appear to be very similar to the other acidulants of this type, although pure aqueous solutions tend to have a slightly bitter taste.
Succinic anhydride, in contrast, is the only commercially available anhydride for food uses.
Amber acid is a colorless odorless prisms or white crystalline powder that melts at 185°C (364 of).
Soluble in water and alcohol, Amber acid is used as a chemical intermediate, Amber acid is used in lacquers,medicine,dyes,and as a taste modifier.
Biochem/physiol Actions of Amber Acid:
Amber acid is a byproduct of anaerobic fermentation in microbes.
Amber acid is a dicarboxylic acid and an intermediate in Kreb′s cycle.
Polymorphism in Amber acid dehydrogenase leads to succinate accumulation.
High levels of Amber acid impairs 2-oxoglutarate epigenetic signalling.
Amber acid levels may modulate tumor progression.
Amber acid inhibits histone demethylation and may contribute to epigenetic changes.
Amber acid is crucial for interleukin-1 β (IL-1β) synthesis during inflammation and immune signalling.
Human Metabolite Information of Amber Acid:
Tissue Locations:
Adipose Tissue
Brain
Fibroblasts
Kidney
Liver
Pancreas
Placenta
Prostate
Skeletal Muscle
Spleen
Cellular Locations:
Endoplasmic reticulum
Extracellular
Mitochondria
Peroxisome
Occurrence of Amber Acid:
Amber acid is found in all plant and animal materials as a result of the central metabolic role played by this dicarboxylic acid in the Citric Acid Cycle.
Amber acid concentrations are monitored in the manufacture of numerous foodstuffs and beverages, including wine, soy sauce, soy bean flour, fruit juice and dairy products (e.g. cheese).
The ripening process of apples can be followed by monitoring the falling levels of Amber acid.
The occurrence of > 5 mg/kg of this acid in egg and egg products is indicative of microbial contamination.
Apart from use as a flavouring agent in the food and beverage industries, Amber acid finds many other non-food applications, such as in the production of dyes, drugs, perfumes, lacquers, photographic chemicals and coolants.
Amber acid is widely distributed in almost all plants, animals and microorganisms where Amber acid is a common intermediate in the intermediary metabolism.
A way to utilise this is with fermentation of biomass by microorganisms.
Amber acid is therefore a good candidate for biobased industrial production.
A concept for a large scale production plant is patented by the company Diversified Natural Products.
The plant consists of a fermentation stage and a separation stage.
During the separations the Amber acid produced in the fermenter is crystallised to the final product, Amber acid.
Preparation of Amber Acid:
Amber acid can also be manufactured by catalytic hydrogenation of malic or fumaric acids.
Amber acid has also been produced commercially by aqueous acid or alkalihydrolysis of succinonitrile derived from ethylene bromide and potassium cyanide.
Today Amber acid is mainly produced from fossil resources through maleic acid hydrogenation.
Amber acid can also be produced through fermentation of sugars.
In that case, in addition to Amber acid, other carboxylic acids (such as lactic acid, formic acid, propionic acid) and alcohols (such as ethanol) are also obtained.
Methods of Manufacturing of Amber Acid:
Hydrogenation of maleic acid, maleic anhydride, or fumaric acid produces good yields of Amber acid.
1,4-Butanediol can be oxidized to Amber acid in several ways: (1) with O2 in an aqueous solution of an alkaline-earth hydroxide at 90-110 °C in the presence of Pd-C; (2) by ozonolysis in aqueous acetic acid; or (3) by reaction with N2O4 at low temperature.
Amber acid can be obtained by phase-transfer-catalyzed reaction of 2-haloacetates, electrolytic dimerization of bromoacetic acid or ester, oxidation of 3-cyanopropanal, and fermentation of n-alkanes.
Amber acid is derived from fermentation of ammonium tartrate.
General Manufacturing Information of Amber Acid:
Industry Processing Sectors:
All other basic organic chemical manufacturing
Plastic material and resin manufacturing
Utilities
Biotechnological Production:
Traditionally, Amber acid is produced by petrochemical synthesis using the precursor maleic acid.
However, there are some microorganisms that are able to produce Amber acid.
Maximum product concentrations of 106 g.L-1 with a yield of 1.25 mol of Amber acid per mole of glucose and a productivity of 1.36 g.L-1.h-1 have been achieved by growing A. succinogenes on glucose.
A high productivity of 10.40 g.L-1.h-1 has been reached with A. succinogenes growing on a complex medium with glucose in a continuous process with an integrated membrane bioreactor-electrodialysis process.
In this process, Amber acid concentration has been 83 g.L-1.
Moreover, metabolic engineering methods were used to develop strains with high productivity and titer as well as low byproduct formation.
For example, growing C. glutamicum strain DldhA-pCRA717 on a defined medium with glucose, a high productivity of 11.80 g.L-1.h-1 with a yield of 1.37 mol of Amber acid per mole of glucose and a titer of 83 g.L-1 has been reported after 7 h.
An extended cultivation resulted in a product concentration of 146 g.L-1 after 46 h.
Handling and Storage of Amber Acid:
Amber acid should be handled in accordance with good industrial hygiene and safety practices.
Avoid contact with eyes, skin, and clothing.
Ensure adequate ventilation in working areas to minimize dust formation.
When handling, use appropriate personal protective equipment.
Store in a cool, dry, and well-ventilated place, away from incompatible substances like strong oxidizers and bases.
Containers should be kept tightly closed and protected from moisture to maintain product quality.
Reactivity and Stability of Amber Acid:
Amber acid is generally stable under recommended storage conditions.
Amber acid is chemically stable at room temperature and under normal atmospheric pressure.
However, Amber acid may react with strong oxidizing agents and strong bases.
At elevated temperatures, Amber acid may decompose, releasing carbon monoxide, carbon dioxide, and other irritating fumes.
Avoid excessive heat and sources of ignition.
First Aid Measures of Amber Acid:
Inhalation:
Move the person to fresh air immediately.
If breathing is difficult, administer oxygen and seek medical attention.
Skin Contact:
Wash affected area thoroughly with soap and water.
Remove contaminated clothing and seek medical advice if irritation persists.
Eye Contact:
Rinse immediately with plenty of water for at least 15 minutes.
Seek medical attention if irritation develops or persists.
Ingestion:
Rinse mouth with water.
Do not induce vomiting unless instructed by medical personnel.
Seek medical attention immediately.
Firefighting Measures of Amber Acid:
Suitable Extinguishing Media:
Use water spray, dry chemical powder, carbon dioxide (CO₂), or appropriate foam.
Specific Hazards Arising from the Chemical:
Thermal decomposition may produce carbon oxides (CO and CO₂).
Protective Equipment for Firefighters:
Wear self-contained breathing apparatus (SCBA) and full protective clothing to prevent contact with skin and eyes during fire situations.
Accidental Release Measures of Amber Acid:
Personal Precautions:
Use personal protective equipment.
Avoid breathing dust and ensure adequate ventilation.
Evacuate personnel to safe areas if necessary.
Environmental Precautions:
Prevent further leakage or spillage if Amber acid can be done safely.
Avoid discharge into drains, surface water, or groundwater.
Methods for Cleaning Up:
Sweep or vacuum the spilled material carefully to avoid dust formation.
Place in a suitable, closed container for disposal according to local regulations.
Exposure Controls / Personal Protective Equipment of Amber Acid:
Engineering Controls:
Provide adequate ventilation, especially in confined areas.
Use local exhaust ventilation where dust may be generated.
Eye Protection:
Safety glasses with side shields or goggles.
Skin Protection:
Protective gloves (e.g., rubber, neoprene) and appropriate protective clothing.
Respiratory Protection:
If exposure limits are exceeded or respiratory irritation occurs, use a NIOSH/MSHA-approved dust respirator.
Hygiene Measures:
Wash hands, forearms, and face thoroughly after handling and before eating, drinking, or smoking.
Remove contaminated clothing and wash before reuse.
Identifiers of Amber Acid:
CAS number: 110-15-6
EC number: 203-740-4
Grade: ChP,NF,JPE,ACS
Hill Formula: C₄H₆O₄
Chemical formula: HOOCCH₂CH₂COOH
Molar Mass: 118.09 g/mol
HS Code: 2917 19 80
CAS Number: 110-15-6
EC Number: 203-740-4
Molecular Formula: C₄H₆O₄
Molecular Weight: 118.09 g/mol
PubChem CID: 1110
ChEBI ID: CHEBI:15741
ChemSpider ID: 1078
UNII: KZK58I7ZUJ
InChI: InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
InChI Key: KDYFGRWQOYBRFD-UHFFFAOYSA-N
SMILES: C(CC(=O)O)C(=O)O
CAS Registry Number: 110-15-6
EC Number: 203-740-4
Molecular Formula: C₄H₆O₄
Molecular Weight: 118.09 g/mol
PubChem CID: 1110
ChEBI ID: CHEBI:15741
ChEMBL ID: CHEMBL519482
ChemSpider ID: 1078
UNII: KZK58I7ZUJ
RTECS Number: WN0350000
Beilstein Reference: 1723850
Merck Index Number: 12, 9220
MDL Number: MFCD00002747
InChI: InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
InChI Key: KDYFGRWQOYBRFD-UHFFFAOYSA-N
Canonical SMILES: C(CC(=O)O)C(=O)O
Standard SMILES: O=C(O)CCC(=O)O
HS Code: 29171980
Properties of Amber Acid:
Molecular Weight: 118.09
XLogP3: -0.6
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 3
Exact Mass: 118.02660867
Monoisotopic Mass: 118.02660867
Topological Polar Surface Area: 74.6 Ų
Heavy Atom Count: 8
Formal Charge: 0
Complexity: 92.6
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Appearance: Colorless to white crystalline solid
Odor: Odorless
Molecular Formula: C₄H₆O₄
Molecular Weight: 118.09 g/mol
Melting Point: 184 °C to 187 °C (363 °F to 369 °F)
Boiling Point (Decomposes): 235 °C (455 °F) – decomposition occurs before true boiling
Density: 1.56 g/cm³ (at 20 °C)
Solubility in Water: Soluble (about 83 g/L at 20 °C)
Solubility in Other Solvents: Slightly soluble in ethanol, ether, acetone
pKa Values:
pKa₁ ≈ 4.21
pKa₂ ≈ 5.64 (indicating it is a weak diprotic acid)
LogP (Partition Coefficient, octanol/water): -0.59 (shows hydrophilic character)
Vapor Pressure: Negligible at 25 °C
Flash Point: 206 °C (403 °F)
Refractive Index: Not applicable for solids (but in solutions can be measured)
Heat of Combustion: Approx. –1,361 kJ/mol
Crystal Structure: Monoclinic
Specifications of Amber Acid:
Boiling point: 235 °C (1013 hPa)
Density:1.57 g/cm3 (25 °C)
Ignition temperature: 470 °C
Melting Point: 188 °C
pH value: 2.7 (10 g/l, H₂O, 20 °C)
Bulk density: 940 kg/m3
Solubility: 58 g/l
Assay (alkalimetric) : 99.0 - 100.5 %
Assay (HPLC) : 99.0 - 100.5 %
Identity (IR) : passes test
Identity (HPLC) : passes test
Identity (wet chemistry) : passes test
In water insoluble matter : ≤ 0.01 %
Melting range (lower value) : ≥ 185.0 °C
Melting range (upper value) : ≤ 190.0 °C
Melting point : 185.0 - 190.0 °C
Chloride (Cl) : ≤ 0.001 %
Phosphate (PO₄) : ≤ 0.001 %
Sulfate (SO₄) : ≤ 0.003 %
Heavy metals (as Pb) : ≤ 0.0020 %
Heavy metals (as Pb) (ACS) : ≤ 5 ppm
Nitrogen compounds (as N) : ≤ 0.001 %
Fe (Iron) : ≤ 5 ppm
As (Arsenic) : ≤ 0.00015 %
Substances reducing permanganate : conforms
Residual solvents (ICH Q3C) : excluded by production process
Sulfated ash (600 °C) : ≤ 0.02 %
Names of Amber Acid:
Regulatory process names:
1,2-Ethanedicarboxylic acid
1,4-Butanedioic acid
Acidum succinicum
Amber acid
Asuccin
Bernsteinsaure
Butandisaeure
Dihydrofumaric acid
DL-Malic acid
Ethylene dicarboxylic acid
Ethylenesuccinic acid
Katasuccin
Kyselina jantarova
Succinate
Succinic acid
Succinic acid
succinic acid
Succinicum acidum
Wormwood acid
CAS names:
Butanedioic acid
IUPAC names:
1,4-Butanedioic acid
Butanedioic Acid
Butanedioic acid
butanedioic acid
Butanedionic acid
Registration dossier
Ethanedicarboxylic acid
Succinic
SUCCINIC ACID
Succinic Acid
Succinic acid
succinic acid
Succinic Acid
Succinic acid
succinic acid
1,4-Butanedioic acid
Butanedioic Acid
Butanedioic acid
butanedioic aci
Butanedionic acid
Ethanedicarboxylic acid
Succinic
Trade names:
Biosuccinium™
Succinic acid
Succinic Acid 99,7
Other identifiers:
110-15-6
2087491-34-5
2087491-34-5
623158-99-6
623158-99-6
