Dihydroxymalonic acid
Encyclopedia
Dihydroxymalonic acid is an organic compound
with formula C3H4O6 or HO-(C=O)-C(OH)2-(C=O)-OH, found in some plants such as alfalfa
and in beet
molasses
.
The compound may also be called dihydroxymesoxalic acid, dihydroxypropanedioic acid. It can be viewed as a hydrate
derivative of mesoxalic acid
, and indeed it is often called mesoxalic acid monohydrate and other silmilar names. This compound is unusual in containing stable geminal
hydroxy
groups.
Dihydroxymalonic acid is a water-soluble white solid. It crystallizes
in deliquescent prisms
that melt between 113°C and 121 °C without loss of water. It has been used in medical research as a hypoglycemic agent. and was patented in the United States in 1997 as a fast-acting antidote
to cyanide
poisoning.
of alloxan
with baryta water, by warming caffuric acid with lead acetate
solution, by electrolysis of tartaric acid in alkaline solution, or from glycerin diacetate
and concentrated nitric acid
in the cold. The product can be obtained also by oxidation of tartronic acid
or glycerol
.
by sodium amalgam
to tartronic acid
, and also combines with phenylhydrazine
and hydroxylamine
. It reduces ammoniacal silver
solutions. When heated with urea
to 100 °C, it forms allantoin
. By continued boiling of its aqueous solution it is decomposed into carbon dioxide
and glyoxylic acid
.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with formula C3H4O6 or HO-(C=O)-C(OH)2-(C=O)-OH, found in some plants such as alfalfa
Alfalfa
Alfalfa is a flowering plant in the pea family Fabaceae cultivated as an important forage crop in the US, Canada, Argentina, France, Australia, the Middle East, South Africa, and many other countries. It is known as lucerne in the UK, France, Australia, South Africa and New Zealand, and known as...
and in beet
Beet
The beet is a plant in the Chenopodiaceae family which is now included in Amaranthaceae family. It is best known in its numerous cultivated varieties, the most well known of which is the purple root vegetable known as the beetroot or garden beet...
molasses
Molasses
Molasses is a viscous by-product of the processing of sugar cane, grapes or sugar beets into sugar. The word molasses comes from the Portuguese word melaço, which ultimately comes from mel, the Latin word for "honey". The quality of molasses depends on the maturity of the sugar cane or sugar beet,...
.
The compound may also be called dihydroxymesoxalic acid, dihydroxypropanedioic acid. It can be viewed as a hydrate
Hydrate
Hydrate is a term used in inorganic chemistry and organic chemistry to indicate that a substance contains water. The chemical state of the water varies widely between hydrates, some of which were so labeled before their chemical structure was understood....
derivative of mesoxalic acid
Mesoxalic acid
Mesoxalic acid, also called oxomalonic acid or ketomalonic acid, is an organic compound with formula C3H2O5 or HO-3-OH.Mesoxalic acid is both a dicarboxylic acid and a ketonic acid. It readily loses two protons to yield the divalent anion C3O52−, called mesoxalate, oxomalonate, or ...
, and indeed it is often called mesoxalic acid monohydrate and other silmilar names. This compound is unusual in containing stable geminal
Geminal
In chemistry, the term geminal refers to the relationship between two functional groups that are attached to the same atom...
hydroxy
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
groups.
Dihydroxymalonic acid is a water-soluble white solid. It crystallizes
Crystallization
Crystallization is the process of formation of solid crystals precipitating from a solution, melt or more rarely deposited directly from a gas. Crystallization is also a chemical solid–liquid separation technique, in which mass transfer of a solute from the liquid solution to a pure solid...
in deliquescent prisms
Prism (geometry)
In geometry, a prism is a polyhedron with an n-sided polygonal base, a translated copy , and n other faces joining corresponding sides of the two bases. All cross-sections parallel to the base faces are the same. Prisms are named for their base, so a prism with a pentagonal base is called a...
that melt between 113°C and 121 °C without loss of water. It has been used in medical research as a hypoglycemic agent. and was patented in the United States in 1997 as a fast-acting antidote
Antidote
An antidote is a substance which can counteract a form of poisoning. The term ultimately derives from the Greek αντιδιδοναι antididonai, "given against"....
to cyanide
Cyanide
A cyanide is a chemical compound that contains the cyano group, -C≡N, which consists of a carbon atom triple-bonded to a nitrogen atom. Cyanides most commonly refer to salts of the anion CN−. Most cyanides are highly toxic....
poisoning.
Synthesis
Dihydroxymalonic acid can be obtained synthetically by hydrolysisHydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
of alloxan
Alloxan
Alloxan is an oxygenated pyrimidine derivative. It is present as alloxan hydrate in aqueous solution.-History:...
with baryta water, by warming caffuric acid with lead acetate
Lead acetate
Lead acetate can refer to:* Lead acetate , Pb4* Lead acetate , Pb2...
solution, by electrolysis of tartaric acid in alkaline solution, or from glycerin diacetate
Acetate
An acetate is a derivative of acetic acid. This term includes salts and esters, as well as the anion found in solution. Most of the approximately 5 billion kilograms of acetic acid produced annually in industry are used in the production of acetates, which usually take the form of polymers. In...
and concentrated nitric acid
Nitric acid
Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosive and toxic strong acid.Colorless when pure, older samples tend to acquire a yellow cast due to the accumulation of oxides of nitrogen. If the solution contains more than 86% nitric acid, it is referred to as fuming...
in the cold. The product can be obtained also by oxidation of tartronic acid
Tartronic acid
Tartronic acid or 2-hydroxymalonic acid is a dicarboxylic acid with the structural formula of HOOCCHCOOH.Its derivative, 2-methyltartronic acid, is isomalic acid.-Uses:...
or glycerol
Glycerol
Glycerol is a simple polyol compound. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. The glycerol backbone is central to all lipids...
.
Reactions
Like typical hydrated ketonic acids, it is reduced in aqueous solutionAqueous solution
An aqueous solution is a solution in which the solvent is water. It is usually shown in chemical equations by appending aq to the relevant formula, such as NaCl. The word aqueous means pertaining to, related to, similar to, or dissolved in water...
by sodium amalgam
Sodium amalgam
Sodium amalgam, commonly denoted Na, is an alloy of mercury and sodium. The term amalgam is used for alloys, intermetallic compounds, and solutions involving mercury as a major component. Sodium amalgam is often used in reactions as strong reducing agents with better handling properties compared...
to tartronic acid
Tartronic acid
Tartronic acid or 2-hydroxymalonic acid is a dicarboxylic acid with the structural formula of HOOCCHCOOH.Its derivative, 2-methyltartronic acid, is isomalic acid.-Uses:...
, and also combines with phenylhydrazine
Phenylhydrazine
Phenylhydrazine is the chemical compound with the formula C6H5NHNH2. Organic chemists abbreviate the compound as PhNHNH2.- Chemical properties :...
and hydroxylamine
Hydroxylamine
Hydroxylamine is an inorganic compound with the formula NH2OH. The pure material is a white, unstable crystalline, hygroscopic compound. However, hydroxylamine is almost always provided and used as an aqueous solution. It is used to prepare oximes, an important functional group. It is also an...
. It reduces ammoniacal silver
Silver
Silver is a metallic chemical element with the chemical symbol Ag and atomic number 47. A soft, white, lustrous transition metal, it has the highest electrical conductivity of any element and the highest thermal conductivity of any metal...
solutions. When heated with urea
Urea
Urea or carbamide is an organic compound with the chemical formula CO2. The molecule has two —NH2 groups joined by a carbonyl functional group....
to 100 °C, it forms allantoin
Allantoin
Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid....
. By continued boiling of its aqueous solution it is decomposed into carbon dioxide
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...
and glyoxylic acid
Glyoxylic acid
Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially....
.