Aldaric acids are a group of

sugar acid In organic chemistry, a sugar acid or acidic sugar is a monosaccharide with a carboxyl group at one end or both ends of its Polymer backbone, chain. Main classes of sugar acids include: * Aldonic acids, in which the aldehyde group () located at t ...

s, where the terminal

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

and

carbonyl In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double bond, double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such a ...

groups of the

sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecul ...

s have been replaced by terminal

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...

s, and are characterised by the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

HO₂C-(CHOH)_n-CO₂H. Oxidation of just the aldehyde yields an

aldonic acid Aldonic acids are sugar acids with the general chemical formula, HO2C(CHOH)nCH2OH. They are obtained by oxidizing the aldehyde (-CHO group) of an aldose to form a carboxylic acid (-COOH group). Aldonic acids are generally found in their ring form ...

while oxidation of just the terminal hydroxyl group yields an

uronic acid 300px, The glucose.html" ;"title="Fischer projections of D-glucose">Fischer projections of D-glucose (left) and D-glucuronic acid (right). Glucose's terminal carbon's primary alcohol group has been oxidized to a carboxylic acid. Uronic acids ...

.) Aldaric acids cannot form cyclic

hemiacetal In organic chemistry, a hemiacetal is a functional group the general formula , where is a hydrogen atom or an organic substituent. They generally result from the nucleophilic Addition reaction, addition of an Alcohol (chemistry), alcohol (a compo ...

s like unoxidized sugars, but they can sometimes form

lactone Lactones are cyclic carboxylic esters. They are derived from the corresponding hydroxycarboxylic acids by esterification. They can be saturated or unsaturated. Lactones are formed by lactonization, the intramolecular esterification of the corresp ...

Synthesis and reactions

Aldaric acids are usually synthesized by the

oxidation Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...

aldose An aldose is a monosaccharide (a simple sugar) with a carbon backbone chain with a carbonyl group on the endmost carbon atom, making it an aldehyde, and hydroxyl groups connected to all the other carbon atoms. Aldoses can be distinguished from ket ...

s with

nitric acid Nitric acid is an inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into nitrogen oxide, oxides of nitrogen. Most com ...

. In this reaction it is the open-chain (polyhydroxyaldehyde) form of the sugar that reacts. These compounds are of interest as bio-derived chemicals including to bio-derived

polyester Polyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include some natura ...

Structure

Nomenclature of the aldaric acids is based on the sugars from which they are derived; for example,

glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...

is oxidized to

glucaric acid Saccharic acid is a chemical compound with the formula C6H10O8. It is an aldaric acid, naturally occurring in fruits and vegetables. The salts of saccharic acid are called saccharates or glucarates. Synthesis Saccharic acid can be prepared by ...

and

xylose Xylose ( , , "wood") is a sugar first isolated from wood, and named for it. Xylose is classified as a monosaccharide of the aldopentose type, which means that it contains five carbon atoms and includes an aldehyde functional group. It is deriv ...

to xylaric acid. Unlike their parent sugars, aldaric acids have the same

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

at both ends of their

carbon chain In chemistry, catenation is the bonding of atoms of the same element into a series, called a ''chain''. A chain or a ring may be ''open'' if its ends are not bonded to each other (an open-chain compound), or ''closed'' if they are bonded in a ...

; therefore, two different sugars can yield the same aldaric acid (this can be understood by looking at the

Fischer projection In chemistry, the Fischer projection, devised by Emil Fischer in 1891, is a two-dimensional representation of a three-dimensional organic molecule by projection. Fischer projections were originally proposed for the depiction of carbohydrates a ...

of a sugar upside down—with normal aldoses, this is a different compound due to the

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

function at the top and the

function at the bottom, but with aldaric acids, there is a

function on both ends, so upside down and right side up do not matter). For example, D-glucaric acid and L-gularic acid are the same compound (but the first name is preferred, because of D- prefix). A consequence of this is that some aldaric acids are

meso form A meso compound or meso isomer is an optically inactive isomer in a set of stereoisomers, at least two of which are optically active. This means that despite containing two or more stereocenters, the molecule is not chiral. A meso compound is sup ...

s with no

optical activity Optical rotation, also known as polarization rotation or circular birefringence, is the rotation of the orientation of the plane of polarization about the optical axis of linearly polarized light as it travels through certain materials. Circul ...

despite their multiple

chiral Chirality () is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek language, Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is dist ...

centers—this occurs if a sugar and its

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

oxidize to the same aldaric acid. An example is D-

galactose Galactose (, ''wikt:galacto-, galacto-'' + ''wikt:-ose#Suffix 2, -ose'', ), sometimes abbreviated Gal, is a monosaccharide sugar that is about as sweetness, sweet as glucose, and about 65% as sweet as sucrose. It is an aldohexose and a C-4 epime ...

—it has four

centers, but D-galactaric and L-galactaric acids, which have the opposite configuration at each chiral center and therefore would be expected to be

s, are actually the same compound; therefore, galactaric acid is an

achiral Chirality () is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is distinguishable from ...

with no

. Again, this can be understood by taking the Fischer projection of either acid and looking at it upside down—the configuration is now switched at every carbon.

Adipic acid Adipic acid or hexanedioic acid is the organic compound with the formula C6H10O4. It a white crystalline powder at standard temperature and pressure. From an industrial perspective, it is the most important dicarboxylic acid at about 2.5 billion ...

, HO₂C(CH₂)₄CO_OH, is not an aldaric acid, but a simple

dicarboxylic acid In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic.Boy Cornils, Peter Lappe "Dicarbox ...

References

* Carey, Francis A. (2006). ''Organic Chemistry'', Sixth Edition, New York, NY: McGraw-Hill. {{ISBN, 0-07-111562-5. Carboxylic acids Dicarboxylic acids Sugar acids