PRODUCTS

HYDROXYBUTANEDIOIC ACID

Hydroxybutanedioic acid is the naturally occurring isomer of Hydroxybutanedioic acid, found mainly in sour and unripe fruits.
Hydroxybutanedioic acid is the most typical acid occurring in fruits, Hydroxybutanedioic acid contributes to sour tastes.
Hydroxybutanedioic acid is used as a food additive, Selective α-amino protecting reagent for amino acid derivatives.

CAS Number: 97-67-6
EC Number: 202-601-5
Molecular Formula: C4H6O5
Molecular Weight (g/mol): 134.087

Synonyms: Hydroxybutanedioic acid, DL-Hydroxybutanedioic acid, 6915-15-7, 2-Hydroxybutanedioic acid, 2-Hydroxysuccinic acid, 617-48-1, malate, hydroxysuccinic acid, Butanedioic acid, hydroxy-, Hydroxybutanedioic acid, DL-, Kyselina jablecna, hydroxybutanedioic acid, Pomalus acid, Deoxytetraric acid, Hydroxybutandisaeure, Musashi-no-Ringosan, alpha-Hydroxysuccinic acid, Caswell No. 537, Monohydroxybernsteinsaeure, Succinic acid, hydroxy-, FDA 2018, R,S(+-)-Hydroxybutanedioic acid, Malicum acidum, Pomalous acid, DL-2-hydroxybutanedioic acid, d,l-Hydroxybutanedioic acid, FEMA Number 2655, 2-Hydroxyethane-1,2-dicarboxylic acid, Kyselina jablecna [Czech], Hydroxybutanedioic acid [NF], (+-)-Hydroxybutanedioic acid, Aepfelsaeure, FEMA No. 2655, CCRIS 2950, CCRIS 6567, (+/-)-Hydroxybutanedioic acid, EPA Pesticide Chemical Code 051101, HSDB 1202, Kyselina hydroxybutandiova, Kyselina hydroxybutandiova [Czech], AI3-06292, H2mal, EINECS 210-514-9, EINECS 230-022-8, UNII-817L1N4CKP, NSC 25941, NSC-25941, 817L1N4CKP, CHEBI:6650, INS NO.296, DTXSID0027640, E296, INS NO. 296, INS-296, Hydroxybutanedioic acid, L-, (+-)-Hydroxysuccinic acid, L-Hydroxybutanedioic acid-1-13C, MLS000084707, DTXCID107640, E-296, (+-)-1-Hydroxy-1,2-ethanedicarboxylic acid, Hydroxybutanedioic acid, (+-)-, dl-Hydroxybutanedioic acid, EC 210-514-9, EC 230-022-8, NSC25941, Hydroxybutanedioic acid (NF), (+/-)-HYDROXYSUCCINIC ACID, DL-MALIC-2,3,3-D3 ACID, SMR000019054, DL-Apple Acid, HYDROXYBUTANEDIOIC ACID, (+/-)-, Hydroxybutanedioic acid (II), Hydroxybutanedioic acid [II], (R)-Hydroxybutanedioic acid, (S)-Hydroxybutanedioic acid, Hydroxybutanedioic acid (USP-RS), Hydroxybutanedioic acid [USP-RS], BUTANEDIOIC ACID, HYDROXY-, (S)-, R-Hydroxybutanedioic acid, Hydroxybutanedioic acid (EP MONOGRAPH), Hydroxybutanedioic acid (USP IMPURITY), Hydroxybutanedioic acid [EP MONOGRAPH], Hydroxybutanedioic acid [USP IMPURITY], Butanedioic acid, 2-hydroxy-, (2S)-, CAS-6915-15-7, L-(-)-MalicAcid, DL-hydroxysuccinic acid, C4H6O5, Hydroxybutanedioic acid, (-)-, MFCD00064213, (+/-)-2-Hydroxysuccinic acid, Racemic Hydroxybutanedioic acid, 180991-05-3, MFCD00064212, .+-.-Hydroxybutanedioic acid, Opera_ID_805, 2-hydroxyl-succinic acid, DL-Hydroxybutanedioic acid, 99%, Hydroxybutanedioic acid [MI], Hydroxybutanedioic acid,(DL), 2-Hydroxydicarboxylic acid, Hydroxybutanedioic acid [FCC], SCHEMBL856, 2-hydroxy-butanedioic acid, bmse000046, bmse000904, D03WNI, Hydroxybutanedioic acid [INCI], Hydroxybutanedioic acid [VANDF], Hydroxybutanedioic acid-, (L-form)-, DL-Hydroxybutanedioic acid, >=99%, HYOSCYAMINEHYDROBROMIDE, Oprea1_130558, Oprea1_624131, Hydroxybutanedioic acid [WHO-DD], butanedioic acid, 2-hydroxy-, DL-HYDROXYSUCOINIC ACID, Butanedioic acid, (.+-.)-, DL(+/-)-Hydroxybutanedioic acid, GTPL2480, 2-HYDROXY-SUCCINIC ACID, DL-HYROXYBUTANEDIOIC ACID, CHEMBL1455497, BDBM92495, DL-Hydroxybutanedioic acid, FCC, >=99%, HMS2358H06, HMS3371C13, (C4-H6-O5)x-, DL-Hydroxybutanedioic acid, analytical standard, HY-Y1311, STR03457, Tox21_201536, Tox21_300372, s9001, STL283959, HYDROXYBUTANEDIOIC ACID [HSDB], AKOS000120085, AKOS017278471, (+/-)-HYDROXYBUTANEDIOIC ACID, AM81418, Butanedioic acid, hydroxy-, (.+.)-, CCG-266122, DB12751, LS-2394, DL-Hydroxybutanedioic acid, ReagentPlus(R), 99%, NCGC00043225-02, NCGC00043225-03, NCGC00254259-01, NCGC00259086-01, 78644-42-5, DL-Hydroxybutanedioic acid, >=98% (capillary GC), LS-88709, SY003313, SY009804, DL-Hydroxybutanedioic acid, ReagentPlus(R), >=99%, DL-Hydroxybutanedioic acid 1000 microg/mL in Methanol, DL-Hydroxybutanedioic acid, USP, 99.0-100.5%, CS-0017784, E 296, EU-0067046, FT-0605225, FT-0625484, FT-0625485, FT-0625539, FT-0632189, M0020, DL-Hydroxybutanedioic acid, SAJ first grade, >=99.0%, EN300-19229, A19426, C00711, C03668, D04843, DL-Hydroxybutanedioic acid, Vetec(TM) reagent grade, 98%, M-0825, AB00443952-12, Hydroxybutanedioic acid, meets USP/NF testing specifications, 4-ethoxyphenyltrans-4-propylcyclohexanecarboxylate, L023999, Q190143, Q-201028, 0C9A2DC0-FEA2-4864-B98B-0597CDD0AD06, F0918-0088, Z104473230, Hydroxybutanedioic acid (CONSTITUENT OF CRANBERRY LIQUID PREPARATION), Hydroxybutanedioic acid, United States Pharmacopeia (USP) Reference Standard, Hydroxybutanedioic acid (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC], Hydroxybutanedioic acid, Pharmaceutical Secondary Standard; Certified Reference Material, DL-Hydroxybutanedioic acid, meets analytical specification of FCC, E296, 99-100.5% (alkalimetric), L-(−)-Hydroxybutanedioic acid, (-)-(S)-Hydroxybutanedioic acid, (-)-L-Hydroxybutanedioic acid, (-)-Hydroxybutanedioic acid, (2S)-2-Hydroxybernsteinsäure [German] [ACD/IUPAC Name], (2S)-2-hydroxybutanedioic acid, (2S)-2-Hydroxysuccinic acid [ACD/IUPAC Name], (S)-(-)-2-Hydroxysuccinic acid, (S)-(−)-2-Hydroxysuccinic acid, (S)-(-)-Hydroxysuccinic acid, (S)-(-)-Hydroxybutanedioic acid, (S)-hydroxy-Butanedioic acid, (S)-Hydroxybutanedioic acid, (S)-Malate, (S)-Hydroxybutanedioic acid, 1723541 [Beilstein], 202-601-5 [EINECS], 97-67-6 [RN], Acide (2S)-2-hydroxysuccinique [French] [ACD/IUPAC Name], Butanedioic acid, 2-hydroxy-, (2S)- [ACD/Index Name], Butanedioic acid, hydroxy-, (2S)-, L-(-)-Hydroxybutanedioic acid, L-Hydroxybutanedioic acid, L-Hydroxysuccinic acid, l-Hydroxybutanedioic acid, Hydroxybutanedioic acid, L-, MFCD00064213 [MDL number], S-(-)-Hydroxybutanedioic acid, S-2-Hydroxybutanedioic acid, (-)-(S)-Malate, (-)-Hydroxysuccinate, (2S)-2-hydroxybutanedioate, (S)-(-)-Hydroxysuccinate, (S)-hydroxy-Butanedioate, (S)-Hydroxybutanedioate, L-Hydroxybutanedioate, L-Hydroxysuccinate, S-(-)-Malate, S-2-Hydroxybutanedioate, (-)-Hydroxysuccinic acid, (??)-Hydroxybutanedioic acid, (S)-(-)-Hydrosuccinic acid, (S)-2-hydroxysuccinic acid, [97-67-6] [RN], 210-514-9 [EINECS], 617-48-1 [RN], 6915-15-7 [RN], 99-98-9 [RN], APPLE ACID, BUTANEDIOIC ACID, HYDROXY-, (S)-, D-malate, FLC, l-(-)-Hydroxybutanedioic acid, ???, L-(-)-Hydroxybutanedioic acid|(2S)-2-Hydroxybutanedioic acid, l-(-)-Hydroxybutanedioic acid-cp, L-2-Hydroxybutanedioic acid, laevo-Hydroxybutanedioic acid, L-Apple acid, l-malicacid, LMR, M-0850, mal, MALATE ION, Hydroxybutanedioic acid, (L), MLT, Oxaloacetate Ion, UNII:J3TZF807X5, UNII-817L1N4CKP, UNII-J3TZF807X5, pinguosuan, L-Mailcacid, L-Hydroxybutanedioic acid, L(-)-Hydroxybutanedioic acid, l-(ii)-malicacid, L-(-)-Hydroxybutanedioic acid, L-(-)-Hydroxybutanedioic acid, CP, L-Hydroxysuccinic acid, L-Gydroxybutanedioicacid, (2S)-2-hydroxybutanedioate, (S)-(-)-Hydroxysuccinic acid, hydroxy-,(S)-Butanedioicacid, Butanedioicacid,hydroxy-,(S)-, (2S)-2-hydroxybutanedioic acid, Butanedioic acid, 2-hydroxy-, (2S)-

Hydroxybutanedioic acid is an organic compound with the molecular formula C4H6O5.
Hydroxybutanedioic acid is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive.

Hydroxybutanedioic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally.
The salts and esters of Hydroxybutanedioic acid are known as malates.
The malate anion is an intermediate in the citric acid cycle.

Hydroxybutanedioic acid is the naturally occurring isomer of Hydroxybutanedioic acid, found mainly in sour and unripe fruits.

Hydroxybutanedioic acid is the most typical acid occurring in fruits, Hydroxybutanedioic acid contributes to sour tastes.
Hydroxybutanedioic acid is commonly used in beverages, confectionary and personal care products.

Hydroxybutanedioic acid, a hydroxydicarboxylic acid, is found in all forms of life.
Hydroxybutanedioic acid exists naturally only as the L-enantiomer.
Hydroxybutanedioic acid should not be confused with the similar sounding maleic and malonic acids.

Hydroxybutanedioic acid gives many fruits, particularly apples, their characteristic flavor.
Hydroxybutanedioic acid is often referred to as “apple acid”.
The word malic is derived from the Latin mālum, for which Malus, the genus that contains all apple species, is also named.

The global market size for Hydroxybutanedioic acid (natural and manufactured1) is ≈US$200 million; the US market is ≈$35 million.
The primary end use in the United States is for flavoring beverages, foods, and confectionaries, with much smaller quantities used in cosmetics and personal care products.
The price of Hydroxybutanedioic acid ranges from US$0.90 to $10.00/kg, depending on the purity, quantity, and end use.

Hydroxybutanedioic acid is used as a food additive, Selective α-amino protecting reagent for amino acid derivatives.
Versatile synthon for the preparation of chiral compounds including κ-opioid receptor agonists, 1α,25-dihydroxyvitamin D3 analogue, and phoslactomycin B.

Hydroxybutanedioic acid is a relevant component of the citric acid cycle that is found in animals, plants and microorganisms.
Hydroxybutanedioic acid is one of the most important fruit acids found in nature and Hydroxybutanedioic acid is the acid present in highest concentrations in wine.

Hydroxybutanedioic acid may be used in food production because Hydroxybutanedioic acid is a stronger acid than citric acid.
Microbial decomposition of Hydroxybutanedioic acid leads to the formation of L-lactate; this can be a desirable reaction in the wine industry, where the level of Hydroxybutanedioic acid is monitored, along with L-lactic acid, during malolactic fermentation.
Hydroxybutanedioic acid may be used as a food preservative (E296) or flavour enhancing additive.

Hydroxybutanedioic acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use only.
Hydroxybutanedioic acid is used at industrial sites.

Hydroxybutanedioic acid is a dicarboxylic acid and organic compound made by all living organisms.
Hydroxybutanedioic acid is responsible for the sour taste of most fruits and is utilized as a food additive.
Ungraded products supplied by Spectrum are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use.

Hydroxybutanedioic acid is nearly odorless with a tart, acidic taste.
Hydroxybutanedioic acid is nonpungent.

Hydroxybutanedioic acid is an organic acid that is commonly found in wine.
Hydroxybutanedioic acid plays an important role in wine microbiological stability.

Hydroxybutanedioic acid can be prepared by hydration of maleic acid; by fermentation from sugar.
Occurs in maple sap, apple, melon, papaya, beer, grape wine, cocoa, sake, kiwifruit and chicory root.

Hydroxybutanedioic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally.
The salts and esters of Hydroxybutanedioic acid are known as malates.

The malate anion is an intermediate in the citric acid cycle.
Hydroxybutanedioic acid, a hydroxydicarboxylic acid, is found in all forms of life.

Hydroxybutanedioic acid exists naturally only as the L-enantiomer.
Hydroxybutanedioic acid should not be confused with the similar sounding maleic and malonic acids.

Hydroxybutanedioic acid is L-hydroxysuccinic acid, by enzyme engineering method or fermentation method and separation and purification.
The content of C4H6Os shall not be less than 99.0% calculated as anhydrous.

Hydroxybutanedioic acid gives many fruits, particularly apples, their characteristic flavor.
Hydroxybutanedioic acid is often referred to as “apple acid”.

The word malic is derived from the Latin mālum, for which Malus, the genus that contains all apple species, is also named.
Hydroxybutanedioic acid is a dicarboxylic acid that is found in many fruits and vegetables.

Hydroxybutanedioic acid is the substrate for the enzyme malate dehydrogenase, which catalyzes the oxidation of L-malate to oxaloacetate.
Hydroxybutanedioic acid is used to study mitochondrial function, as Hydroxybutanedioic acid can be used as an alternative energy source.

The Hydroxybutanedioic acid monosodium salt (LAM) has been shown to be effective in preventing muscle damage caused by exercise.
This may be due to Hydroxybutanedioic acid's ability to decrease oxidative stress and increase ATP production through increased mitochondrial activity.

Hydroxybutanedioic acid also has been shown to promote photoreceptor cell survival and improve retinal function in animals with damaged photoreceptors, although Hydroxybutanedioic acid does not have any effect on normal animal eyes.
Hydroxybutanedioic acid, is an alpha-hydroxy organic acid, is sometimes referred to as a fruit acid.

Hydroxybutanedioic acid is found in apples and other fruits.
Hydroxybutanedioic acid is also found in plants and animals, including humans.

In fact, Hydroxybutanedioic acid, in the form of Hydroxybutanedioic acid anion malate, is a key intermediate in the major biochemical energy-producing cycle in cells known as the citric acid or Krebs cycle located in the cells' mitochondria.
Hydroxybutanedioic acid is used in many food products and is a very popular product in beverages and sweets.
Hydroxybutanedioic acid, also known as apple acid and hydroxysuccinic acid, is a chiral molecule.

Hydroxybutanedioic acid, disodium salt is a dicarboxylic acid used to differentiate microorganisms based on their varying metabolic properties.
Hydroxybutanedioic acid is a source of CO2 in the Calvin cycle and an intermediate of the citric acid cycle.

Hydroxybutanedioic acid, is a naturally occurring carboxylic acid abundantly present in the human body.
This acid is not only found in the human body but also occurs naturally in a wide range of foods.

Moreover, Hydroxybutanedioic acid is produced during the fermentation of carbohydrates.
Beyond Hydroxybutanedioic acid biological significance, Hydroxybutanedioic acid finds application in diverse industrial sectors.

Hydroxybutanedioic acid contributes to the production of plastics, solvents, and detergents.
However, the precise mechanism of action of Hydroxybutanedioic acid remains partially understood.

Hydroxybutanedioic acid is hypothesized to be involved in ATP production and the transport of electrons within the electron transport chain.
Furthermore, Hydroxybutanedioic acid is believed to partake in the metabolism of carbohydrates, fats, and proteins.

Hydroxybutanedioic acid is a dicarboxylic acid found in fruits and vegetables, especially apples.
The name Hydroxybutanedioic acid comes from the Latin word for apple, mālum.

Many fruits owe their tart and sour flavors to Hydroxybutanedioic acid.
The salts and esters of Hydroxybutanedioic acid are known as malate.

Many supplements bond to malate to improve their bioavailability, such as citrulline malate and magnesium malate.
Malate is also part of the citric acid cycle (CAC), sometimes referred to as the Krebs cycle or the tricarboxylic acid cycle (TCA).

The CAC is the primary pathway that delivers energy to all areas of the body.
The CAC uses malate to produce NADPH, which then converts to NADH.

NADH is essential for producing adenosine triphosphate (ATP), also known as the energy currency for cells.
ATP provides the necessary energy for various chemical reactions and biochemical processes that occur throughout the body.

Hydroxybutanedioic acid has many uses in food, beverage, pharmaceutical, chemical and medical industries.
Hydroxybutanedioic acid can be produced by one-step fermentation, enzymatic transformation of fumaric acid to L-malate and acid hydrolysis of polyHydroxybutanedioic acid.

However, the process for one-step fermentation is preferred as Hydroxybutanedioic acid has many advantages over any other process.
The pathways of Hydroxybutanedioic acid biosynthesis in microorganisms are partially clear and three metabolic pathways including non-oxidative pathway, oxidative pathway and glyoxylate cycle for the production of Hydroxybutanedioic acid from glucose have been identified.

Usually, high levels of L-malate are produced under the nitrogen starvation conditions, L-malate, as a calcium salt, is secreted from microbial cells and CaCO3 can play an important role in calcium malate biosynthesis and regulation.
However, Hydroxybutanedioic acid is still unclear how Hydroxybutanedioic acid is secreted into the medium.
To enhance L-malate biosynthesis and secretion by microbial cells, Hydroxybutanedioic acid is very important to study the mechanisms of Hydroxybutanedioic acid biosynthesis and secretion at enzymatic and molecular levels.

Hydroxybutanedioic acid is formed as a by-product of the metabolic processes of sugars and occurs under several names, such as:
Hydroxysuccinic acid,
2-hydroxybutanedioic acid,
Acidum malicum,
Hydroxybutanedioic acid,
Acidity regulator E296.

Hydroxybutanedioic acid belongs to the group of natural hydroxy acids.
This means that the molecule contains a hydroxyl group, consisting of oxygen (O) and hydrogen (H).

The structural formula of acidum malicum is as follows:
HOOC–CH(OH)–CH2–COOH.

The molecular formula for Hydroxybutanedioic acid is: C4H6O5.
As an optically active compound, this acid is classified into two forms:

L-Hydroxybutanedioic acid (left-handed form, found in fruits),
D-Hydroxybutanedioic acid (right-handed form, does not occur in nature).
As a result of industrial treatment of hydroxysuccinic acid, a mixture in the form of a racemate (DHydroxybutanedioic acid), which has no optical activity, is formed.

Applications of Hydroxybutanedioic acid:
Hydroxybutanedioic acid is used as a food additive, Selective α-amino protecting reagent for amino acid derivatives.
Versatile synthon for the preparation of chiral compounds including κ-opioid receptor agonists, 1α,25-dihydroxyvitamin D3 analogue, and phoslactomycin B.

Hydroxybutanedioic acid may be used to prepare:
Diethyl (S)-malate
Ethyl (R)-2-hydroxyl-4-phenylbutanoate
Ethyl (S)-2-hydroxyl-4-phenylbutanoate
D-homophenylalanine ethyl ester hydrochloride
Furo[3,2-i]indolizines

Uses of Hydroxybutanedioic acid:
Hydroxybutanedioic acid may improve dry mouth, dry mouth caused by medication in particular.
Hydroxybutanedioic acid helps produce more saliva due to Hydroxybutanedioic acid sour flavor.

One six-week study examined the effects of a Hydroxybutanedioic acid spray solution on dry mouth compared to a placebo.
The Hydroxybutanedioic acid group had noticeably improved dry mouth symptoms and better saliva flow than the placebo group.

Another two-week trial produced similar results.
Most individuals tolerate Hydroxybutanedioic acid well, given that Hydroxybutanedioic acid’s a common compound in many fruits and vegetables.

Hydroxybutanedioic acid may cause mild side effects, including nausea, diarrhea, and headaches.
Individuals taking medications to lower their blood pressure should consult with a physician before taking Hydroxybutanedioic acid supplements, as they may lower blood pressure.

Kidney stones are painful and can affect many people.
Hydroxybutanedioic acid has been researched for Hydroxybutanedioic acid potential role in preventing and treating kidney stones.

In one preliminary study set in a lab, Hydroxybutanedioic acid was found to increase urine pH levels, making kidney stone formation less likely.
The researchers concluded that Hydroxybutanedioic acid supplementation might help treat calcium kidney stones.4

A 2016 review on the importance of a healthy diet to prevent kidney stones suggested pears could be a potential treatment option.
Per the review, the Hydroxybutanedioic acid in pears may be used to prevent the formation of kidney stones.
This is because Hydroxybutanedioic acid is a precursor for citrate, a compound that inhibits crystal growth in the kidneys.

Hydroxybutanedioic acid contains natural emollient ingredients, which can remove wrinkles on the skin surface, make the skin become tender and white, smooth and elastic, so in the cosmetic formula favored; Hydroxybutanedioic acid can be formulated a variety of flavors, spices, for a variety of daily chemical products, such as toothpaste, shampoo, etc.
Hydroxybutanedioic acid is used abroad to replace citric acid as a new type of detergent additive for the synthesis of high-grade special detergents.

Hydroxybutanedioic acid can be used in pharmaceutical preparations, tablets, syrup, can also be mixed into the amino acid solution, can significantly improve the absorption rate of amino acids; Hydroxybutanedioic acid can be used for the treatment of liver disease, anemia, low immunity, uremia, hypertension, liver failure and other diseases, and can reduce the toxic effect of anticancer drugs on normal cells; Can also be used for the preparation and synthesis of insect repellents, anti-Tartar agents.
In addition, Hydroxybutanedioic acid can also be used as industrial cleaning agent, resin curing agent, synthetic material plasticizer, feed additive, etc.

Hydroxybutanedioic acid is used to resolve α-phenylethylamine, a versatile resolving agent in Hydroxybutanedioic acid own right.

Hydroxybutanedioic acid is found in unripe apples and other fruit.
Hydroxybutanedioic acid is used to make wine, stucco (plaster), cosmetics, pharmaceuticals, dentifrices, and coumarin derivatives.

Hydroxybutanedioic acid is also used as a chelating agent, metal cleaner, electroplating chemical, acidulant, discoloration inhibitor, food flavor, and antioxidant for fats and oils.
Hydroxybutanedioic acid is naturally occurring biochemical that can be converted into citric acid in the citric acid cycle.

Hydroxybutanedioic acid is used as a preservative in animal feeds.
Hydroxybutanedioic acid is used as a flavoring agent and acidity regulator in food.
Hydroxybutanedioic acid is permitted for use as an inert ingredient in non-food pesticide products

Hydroxybutanedioic acid is intermediate in chemical synthesis.
Hydroxybutanedioic acid is chelating and buffering agent.

Hydroxybutanedioic acid is flavoring agent, flavor enhancer and acidulant in foods.
Hydroxybutanedioic acid is manufacture of various esters and salts, wine manufacture, chelating agent, food acidulant, flavoring.

Natural acids of organic origin have long been used in industry.

Hydroxybutanedioic acid serves, among others, as a preservative and acidity regulator – such as the popular E296 – that’s added to:
Preserves,
Jams,
Marmalade,
Candy,
Jellies, etc.

In food production, an ingredient called E296 is used as one of the best citric acid substitutes.
Hydroxybutanedioic acid makes the products stay fresh and attractive for longer.
The acid is effective in impeding the appearance of clouding and the loss of colour of various substances.

In chemical industry, Hydroxybutanedioic acid is also useful in the process of organic synthesis.
Thanks to this, Hydroxybutanedioic acid is possible to obtain, among others, esters used in the production of cleaning agents and cosmetics.

Manufacturers in the pharmaceutical industry make good use of the beneficial properties of acidum malicum.
Organic acid is a healthy stimulant for the digestive system and improves the condition of the epidermis, and therefore Hydroxybutanedioic acid is used as an ingredient in medicinal rinses, capsules and dietary supplements.

Use in cosmetics and the beauty industry:
The antibacterial, stabilising, preserving and brightening properties of acidum malicum are appreciated especially by manufacturers from the cosmetic and beauty industries.

Hydroxybutanedioic acid is used as an ingredient in many cosmetics for everyday use, such as:
Moisturising and anti-wrinkle creams,
Brightening masks for face and hair,
Shampoos and hair rinses (including bleaches, colour fixers),
Regenerating and cleansing milks and tonics (soothing, brightening, anti-acne),
Natural rinses for hair and nails.

In recent years, people associated with the beauty industry have also become interested in Hydroxybutanedioic acid.
This antibacterial and antioxidant compound is more and more often used for specialised cosmetology treatments for skin and hair.

Among others, these are:
Brightening masks,
Exfoliating scrubs for the face and body,
Aesthetic anti-ageing treatments.

Treatments with Hydroxybutanedioic acid are aimed at improving the condition of the epidermis, inhibiting bacterial growth and the ageing of cells.
Exposing the skin to intense acid action also helps to get rid of discolouration, blemishes and shrink unattractive-looking pores.

Uses at industrial sites:
Hydroxybutanedioic acid is used in the following products: laboratory chemicals and pharmaceuticals.
Hydroxybutanedioic acid is used for the manufacture of: chemicals.
Release to the environment of Hydroxybutanedioic acid can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).

Industry Uses:
Cleaning agent
Not Known or Reasonably Ascertainable
Other (specify)
Preservative
Process regulators

Consumer Uses:
Not Known or Reasonably Ascertainable
Other (specify)
Preservative
Process regulators

Industrial Processes with risk of exposure:
Acid and Alkali Cleaning of Metals
Electroplating
Farming (Feed Additives)

Plant defense of Hydroxybutanedioic acid:
Soil supplementation with molasses increases microbial synthesis of MA.
This is thought to occur naturally as part of soil microbe suppression of disease, so soil amendment with molasses can be used as a crop treatment in horticulture.

Benefits of Hydroxybutanedioic acid:

Potential Hydroxybutanedioic acid Benefits For Exercise Performance:
Hydroxybutanedioic acid may improve exercise performance by boosting energy and decreasing muscle fatigue.
Hydroxybutanedioic acid also enhances the absorption of other sports performance enhancers like creatine and citrulline.

One study found that a creatine-malate combination improved several aspects of athletes’ running performance, including peak power, distance traveled, hormone levels, and total work.
Bonding Hydroxybutanedioic acid with citrulline produces citrulline malate.
Hydroxybutanedioic acid enhances citrulline’s innate ability to improve nitric oxide levels, remove muscle waste, increase energy, and reduce muscle soreness.

Potential Hydroxybutanedioic acid Benefits For Dry Mouth:
Hydroxybutanedioic acid may improve dry mouth, dry mouth caused by medication in particular.
Hydroxybutanedioic acid helps produce more saliva due to Hydroxybutanedioic acid sour flavor.

One six-week study examined the effects of a Hydroxybutanedioic acid spray solution on dry mouth compared to a placebo.
Hydroxybutanedioic acid group had noticeably improved dry mouth symptoms and better saliva flow than the placebo group.
Another two-week trial produced similar results.

Biochem/physiol Actions of Hydroxybutanedioic acid:
Hydroxybutanedioic acid is a part of cellular metabolism.
Hydroxybutanedioic acid's application is recognized in pharmaceutics.

Hydroxybutanedioic acid is useful in the treatment of hepatic malfunctioning, effective against hyper-ammonemia.
Hydroxybutanedioic acid is used as a part of amino acid infusion.

Hydroxybutanedioic acid also serves as a nanomedicine in the treatment of brain neurological disorders.
A TCA (Krebs cycle) intermediate and partner in the Hydroxybutanedioic acid aspartate shuttle.

Hydroxybutanedioic acid is the naturally occurring form, whereas a mixture of L- and D-Hydroxybutanedioic acid is produced synthetically.
Malate plays an important role in biochemistry.

In the C4 carbon fixation process, malate is a source of CO2 in the Calvin cycle.
In the citric acid cycle, (S)-malate is an intermediate, formed by the addition of an -OH group on the si face of fumarate.

Hydroxybutanedioic acid can also be formed from pyruvate via anaplerotic reactions.
Hydroxybutanedioic acid is also synthesized by the carboxylation of phosphoenolpyruvate in the guard cells of plant leaves.

Hydroxybutanedioic acid , as a double anion, often accompanies potassium cations during the uptake of solutes into the guard cells in order to maintain electrical balance in the cell.
The accumulation of these solutes within the guard cell decreases the solute potential, allowing water to enter the cell and promote aperture of the stomata.

General Manufacturing Information of Hydroxybutanedioic acid:

Industry Processing Sectors:
All Other Basic Inorganic Chemical Manufacturing
Computer and Electronic Product Manufacturing
Food, beverage, and tobacco product manufacturing
Not Known or Reasonably Ascertainable
Soap, Cleaning Compound, and Toilet Preparation Manufacturing

Biochemistry of Hydroxybutanedioic acid:
Hydroxybutanedioic acid is the naturally occurring form, whereas a mixture of L- and D-Hydroxybutanedioic acid is produced synthetically.

Hydroxybutanedioic acid plays an important role in biochemistry.
In the C4 carbon fixation process, malate is a source of CO2 in the Calvin cycle.

In the citric acid cycle, (S)-malate is an intermediate, formed by the addition of an -OH group on the si face of fumarate.
Hydroxybutanedioic acid can also be formed from pyruvate via anaplerotic reactions.

Hydroxybutanedioic acid is also synthesized by the carboxylation of phosphoenolpyruvate in the guard cells of plant leaves.
Hydroxybutanedioic acid, as a double anion, often accompanies potassium cations during the uptake of solutes into the guard cells in order to maintain electrical balance in the cell.
The accumulation of these solutes within the guard cell decreases the solute potential, allowing water to enter the cell and promote aperture of the stomata.

In food:
Hydroxybutanedioic acid was first isolated from apple juice by Carl Wilhelm Scheele in 1785.
Antoine Lavoisier in 1787 proposed the name acide malique, which is derived from the Latin word for apple, mālum—as is Hydroxybutanedioic acid genus name Malus.

In German Hydroxybutanedioic acid is named Äpfelsäure (or Apfelsäure) after plural or singular of a sour thing from the apple fruit, but the salt(s) are called Malat(e).
Hydroxybutanedioic acid is the main acid in many fruits, including apricots, blackberries, blueberries, cherries, grapes, mirabelles, peaches, pears, plums, and quince and is present in lower concentrations in other fruits, such as citrus.

Hydroxybutanedioic acid contributes to the sourness of unripe apples.
Sour apples contain high proportions of the acid.

Hydroxybutanedioic acid is present in grapes and in most wines with concentrations sometimes as high as 5 g/L.
Hydroxybutanedioic acid confers a tart taste to wine; the amount decreases with increasing fruit ripeness.

The taste of Hydroxybutanedioic acid is very clear and pure in rhubarb, a plant for which Hydroxybutanedioic acid is the primary flavor.
Hydroxybutanedioic acid is also the compound responsible for the tart flavor of sumac spice.
Hydroxybutanedioic acid is also a component of some artificial vinegar flavors, such as "salt and vinegar" flavored potato chips.

In citrus, fruits produced in organic farming contain higher levels of Hydroxybutanedioic acid than fruits produced in conventional agriculture.

The process of malolactic fermentation converts Hydroxybutanedioic acid to much milder lactic acid.
Hydroxybutanedioic acid occurs naturally in all fruits and many vegetables, and is generated in fruit metabolism.

Hydroxybutanedioic acid, when added to food products, is denoted by E number E296.
Hydroxybutanedioic acid is sometimes used with or in place of the less sour citric acid in sour sweets.

These sweets are sometimes labeled with a warning stating that excessive consumption can cause irritation of the mouth.
Hydroxybutanedioic acid is approved for use as a food additive in the EU, US and Australia and New Zealand (where Hydroxybutanedioic acid is listed by its INS number 296).

Hydroxybutanedioic acid contains 10 kJ (2.39 kilocalories) of energy per gram.

Pharmacology and Biochemistry of Hydroxybutanedioic acid:

Bionecessity:
Hydroxybutanedioic acid is an intermediate in the citric acid cycle.
Hydroxybutanedioic acid is formed from fumaric acid and is oxidized to oxaloacetic acid.

Hydroxybutanedioic acid is also metabolized to pyruvic acid by malic enzyme which is present in many biologic systems, including bacteria and plants.
L-Malic and dHydroxybutanedioic acid are both rapidly metabolized in the rat.

Orally or ip administered l- or dHydroxybutanedioic acid was extensively eliminated as carbon dioxide (83 to 92%).
No differences between the two forms were found in the rates (90 to 95% in 24 hr) or routes of excretion.

Malate occurs in all living organisms as an intermediate in the citric acid cycle.
Hydroxybutanedioic acid occurs in relatively high amounts in many fruits and vegetables.
Hydroxybutanedioic acid has two stereoisomeric forms (L- and D-enantiomers), although only the L-isomer exists naturally.

Production and Main Reactions of Hydroxybutanedioic acid:
Racemic Hydroxybutanedioic acid is produced industrially by the double hydration of maleic anhydride.
In 2000, American production capacity was 5,000 tons per year.

The enantiomers may be separated by chiral resolution of the racemic mixture.
S-Hydroxybutanedioic acid is obtained by fermentation of fumaric acid.

Self-condensation of Hydroxybutanedioic acid in the presence of fuming sulfuric acid gives the pyrone couHydroxybutanedioic acid.

Note that this scheme is incorrect. 4 H2O and 2 CO (carbon monoxide, not carbon dioxide) are liberated during the condensation.

Hydroxybutanedioic acid was important in the discovery of the Walden inversion and the Walden cycle, in which (−)-Hydroxybutanedioic acid first is converted into (+)-chlorosuccinic acid by action of phosphorus pentachloride.
Wet silver oxide then converts the chlorine compound to (+)-Hydroxybutanedioic acid, which then reacts with PCl5 to the (−)-chlorosuccinic acid.
The cycle is completed when silver oxide takes Hydroxybutanedioic acid back to (−)-Hydroxybutanedioic acid.

Etymology of Hydroxybutanedioic acid:
The word 'malic' is derived from Latin 'mālum', meaning 'apple'.
The related Latin word mālus, meaning 'apple tree', is used as the name of the genus Malus, which includes all apples and crabapples; and the origin of other taxonomic classifications such as Maloideae, Malinae, and Maleae.

Handling and storage of Hydroxybutanedioic acid:

Conditions for safe storage, including any incompatibilities:

Storage conditions:
Tightly closed.
Dry.

Storage class:
Storage class (TRGS 510): 11: Combustible Solids

Stability and reactivity of Hydroxybutanedioic acid:

Reactivity:
The following applies in general to flammable organic substances and mixtures:
In correspondingly fine distribution, when whirled up a dust explosion potential may generally be assumed.

Chemical stability:
Hydroxybutanedioic acid is chemically stable under standard ambient conditions (room temperature).

Possibility of hazardous reactions:

Violent reactions possible with:
Bases
Oxidizing agents
Reducing agents
Alkali metals

Conditions to avoid:
Heat.

First aid measures of Hydroxybutanedioic acid:

General advice:
Show Hydroxybutanedioic acid safety data sheet to the doctor in attendance.

If inhaled:

After inhalation:
Fresh air.

In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.

In case of eye contact:

After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.

If swallowed

After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.

Firefighting measures of Hydroxybutanedioic acid:

Suitable extinguishing media:
Water Foam Carbon dioxide (CO2) Dry powder

Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.

Special hazards arising from Hydroxybutanedioic acid or mixture:
Carbon oxides
Combustible.
Development of hazardous combustion gases or vapours possible in the event of fire.

Advice for firefighters:
Stay in danger area only with self-contained breathing apparatus.
Prevent skin contact by keeping a safe distance or by wearing suitable protective clothing.

Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

Accidental release measures of Hydroxybutanedioic acid:

Personal precautions, protective equipment and emergency procedures:

Advice for non-emergency personnel:
Avoid inhalation of dusts.
Avoid substance contact.

Ensure adequate ventilation.
Evacuate the danger area, observe emergency procedures, consult an expert.

Environmental precautions:
Do not let product enter drains.

Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.

Observe possible material restrictions,
Take up dry.

Dispose of properly.
Clean up affected area.
Avoid generation of dusts.

Identifiers of Hydroxybutanedioic acid:
CAS Number: 6915-15-7

ChEBI:
CHEBI:6650
CHEBI:30796 D-(+)
CHEBI:30797 L-(–)

ChEMBL: ChEMBL1455497

ChemSpider:
510
83793 D-(+)-Hydroxybutanedioic acid
193317 L-(–)-Hydroxybutanedioic acid

ECHA InfoCard: 100.027.293
EC Number: 230-022-8
E number: E296 (preservatives)
IUPHAR/BPS: 2480

KEGG:
C00711
C00497 D-(+)
C00149 L-(–)

PubChem CID:
525
92824 D-(+)
222656 L-(–)

UNII: 817L1N4CKP
CompTox Dashboard (EPA): DTXSID0027640
InChI: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
Key: BJEPYKJPYRNKOW-UHFFFAOYSA-N
InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
Key: BJEPYKJPYRNKOW-UHFFFAOYAM
SMILES: O=C(O)CC(O)C(=O)O

CAS: 97-67-6
Molecular Formula: C4H6O5
Molecular Weight (g/mol): 134.087
MDL Number: MFCD00064213
InChI Key: BJEPYKJPYRNKOW-REOHCLBHSA-N
PubChem CID: 222656
ChEBI: CHEBI:30797
IUPAC Name: (2S)-2-hydroxybutanedioic acid
SMILES: C(C(C(=O)O)O)C(=O)O
Synonym(s): (S)-(−)-2-Hydroxysuccinic acid, L-Hydroxybutanedioic acid
Linear Formula: HO2CCH2CH(OH)CO2H
CAS Number: 97-67-6
Molecular Weight: 134.09
Beilstein: 1723541
EC Number: 202-601-5
MDL number: MFCD00064213
PubChem Substance ID: 24896463
NACRES: NA.22

CAS number: 97-67-6
EC number: 202-601-5
Hill Formula: C₄H₆O₅
Chemical formula: HOOCCH(OH)CH₂COOH
Molar Mass: 134.08 g/mol
HS Code: 2918 19 98

Properties of Hydroxybutanedioic acid:
Chemical formula: C4H6O5
Molar mass: 134.09 g/mol
Appearance: Colorless
Density: 1.609 g⋅cm−3
Melting point: 130 °C (266 °F; 403 K)
Solubility in water: 558 g/L (at 20 °C)
Acidity (pKa): pKa1 = 3.40
pKa2 = 5.20

Quality Level: 200 - 300
Assay: ≥95% (titration)
form: powder
pKa (25 °C): (1) 3.46, (2) 5.10
mp: 101-103 °C (lit.)
solubility: water: 100 mg/mL, clear to very slightly hazy, colorless
SMILES string: O[C@@H](CC(O)=O)C(O)=O
InChI: 1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
InChI key: BJEPYKJPYRNKOW-REOHCLBHSA-N

Boiling point: 140 °C (decomposition)
Density: 1.60 g/cm3 (20 °C)
Melting Point: 98 - 103 °C
pH value: 2.2 (10 g/l, H₂O, 20 °C)
Bulk density: 600 kg/m3
Solubility: 160 g/l

Molecular Weight: 134.09 g/mol
XLogP3: -1.3
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 5
Rotatable Bond Count: 3
Exact Mass: 134.02152329 g/mol
Monoisotopic Mass: 134.02152329 g/mol
Topological Polar Surface Area: 94.8Å²
Heavy Atom Count: 9
Complexity: 129
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Hydroxybutanedioic acid:
Assay (acidimetric): ≥ 99.0 %
Melting range (lower value): ≥ 98 °C
Melting range (upper value): ≤ 104 °C
Spec. rotation [α²0/D (c=5 in pyridine): -30.0 - -27.0 °
Identity (IR): passes test

Melting Point: 100°C to 106°C
Color: White
Density: 1.6
Flash Point: 220°C (428°F)
Quantity: 2.5 kg
Beilstein: 1723541
Merck Index: 14,5707
Solubility Information: Soluble in water(363g/L).
Optical Rotation: −26° (c=5.5 in pyridine)
Formula Weight: 134.09
Percent Purity: 99%
Physical Form: Crystalline Powder
Chemical Name or Material: L-(-)-Hydroxybutanedioic acid

Related compounds of Hydroxybutanedioic acid:
Butanol
Butyraldehyde
Crotonaldehyde
Sodium malate

Other anions:
Malate

Related carboxylic acids:
Succinic acid
Tartaric acid
Fumaric acid

Related Products of Hydroxybutanedioic acid:
2,3-Dichlorophenoxyacetic Acid
D674580
rac Geosmin
Germacrene D (~90%) (Stabilized with Hydroquinone)
Germacrene D-d3

Names of Hydroxybutanedioic acid:

Regulatory process names:
(-)-Hydroxysuccinic acid
(-)-Hydroxybutanedioic acid
2-Hydroxybutanedioic acid, (S)-
Apple acid
Butanedioic acid, 2-hydroxy-, (2S)-
Butanedioic acid, hydroxy-, (2S)-
Butanedioic acid, hydroxy-, (S)-
Butanedioic acid, hydroxy-, (S)- (9CI)
Hydroxybutanedioic acid, (S)-
Hydroxysuccinnic acid (-)
L-(-)-Hydroxybutanedioic acid
L-Hydroxybutanedioic acid
L-Hydroxybutanedioic acid
Hydroxybutanedioic acid L-(-)-form
Hydroxybutanedioic acid, L-
S-(-)-Hydroxybutanedioic acid
S-2-Hydroxybutanedioic acid

IUPAC names:
(2S)-2-hydroxybutanedioic acid
(S)-(−)-2-Hydroxysuccinic acid
2-hydroxybutanedioic acid
Butenedioic acid
L(-)-Hydroxybutanedioic acid
L-(-)-Hydroxybutanedioic acid
L-(-)-Äpfelsäure
L-Hydroxybutanedioic acid
L-Hydroxysuccinic acid
l-hydroxysuccinic acid
L-Hydroxybutanedioic acid
L-Hydroxybutanedioic acid
L-Hydroxybutanedioic acid
L-Hydroxybutanedioic acid
Hydroxybutanedioic acid
S-2-Hydroxybutanedioic acid
S-HYDROXYBUTANEDIOIC ACID

Preferred IUPAC name:
2-Hydroxybutanedioic acid

Trade names:
Acido Malico
L-(-)-Hydroxybutanedioic acid

Other names:
Hydroxybutanedioic acid
2-Hydroxysuccinic acid
(L/D)-Hydroxybutanedioic acid
(±)-Hydroxybutanedioic acid
(S/R)-Hydroxybutanedioic acid

Other identifiers:
124501-05-9
498-37-3
6294-10-6
84781-39-5
97-67-6