cis-aconitic acid | |
trans-aconitic acid | |
Names | |
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Preferred IUPAC name Prop-1-ene-1,2,3-tricarboxylic acid | |
Other names Achilleic acid; equisetic acid; citridinic acid; pyrocitric acid; achilleaic acid; acinitic acid | |
Identifiers | |
ChemSpider |
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ECHA InfoCard | 100.007.162 |
PubChem CID |
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UNII |
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CompTox Dashboard (EPA) | |
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Properties | |
C6H6O6 | |
Molar mass | 174.108 g·mol−1 |
Appearance | Colorless crystals |
Melting point | 190 °C (374 °F; 463 K) (decomposes) (mixed isomers), 173 °C (cis and trans isomers) |
Acidity (pKa) | 2.80, 4.46 (trans isomer) [2] 2.78, 4.41, 6.21 (cis isomer) [3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Aconitic acid refers to organic compounds with the formula HO2CCH2C(CO2H)=CHCO2H. A white solid, it is clasified as a tricarboxylic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerization of citrate to isocitrate in the citric acid cycle. It is acted upon by the enzyme aconitase.
Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid: [4]
A mixture of isomers are generated in this way.
Aconitic acid was originally isolated from Aconitum napellus by Swiss chemist and apothecary Jacques Peschier in 1820. [5] [6] It was first prepared by thermal dehydration. [7]
Like the conjugate bases of other polycarboxylic acid, acotinic acid forms a variety of coordination complexes. One example is the coordination polymer [Zn3(C6H3O6)2(H2O)6]n. [8]
In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. These compounds contain a distinctive functional group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.
Citric acid is an organic compound with the formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in the metabolism of all aerobic organisms.
Cystine is the oxidized derivative of the amino acid cysteine and has the formula (SCH2CH(NH2)CO2H)2. It is a white solid that is poorly soluble in water. As a residue in proteins, cystine serves two functions: a site of redox reactions and a mechanical linkage that allows proteins to retain their three-dimensional structure.
Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.
The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring. Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution.
In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.
A dipeptide is an organic compound derived from two amino acids. The constituent amino acids can be the same or different. When different, two isomers of the dipeptide are possible, depending on the sequence. Several dipeptides are physiologically important, and some are both physiologically and commercially significant. A well known dipeptide is aspartame, an artificial sweetener.
In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile". The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.
In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. The compounds are structurally related to acid anhydrides, although imides are more resistant to hydrolysis. In terms of commercial applications, imides are best known as components of high-strength polymers, called polyimides. Inorganic imides are also known as solid state or gaseous compounds, and the imido group (=NH) can also act as a ligand.
Cyclohexa-1,3-diene is an organic compound with the formula (C2H4)(CH)4. It is a colorless, flammable liquid. Its refractive index is 1.475 (20 °C, D). It is one of two isomers of cyclohexadiene, the other being 1,4-cyclohexadiene.
Manganese(II) chloride is the dichloride salt of manganese, MnCl2. This inorganic chemical exists in the anhydrous form, as well as the dihydrate (MnCl2·2H2O) and tetrahydrate (MnCl2·4H2O), with the tetrahydrate being the most common form. Like many Mn(II) species, these salts are pink, with the paleness of the color being characteristic of transition metal complexes with high spin d5 configurations.
Thionyl chloride is an inorganic compound with the chemical formula SOCl2. It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.
An isocyanide is an organic compound with the functional group –N+≡C−. It is the isomer of the related nitrile (–C≡N), hence the prefix is isocyano. The organic fragment is connected to the isocyanide group through the nitrogen atom, not via the carbon. They are used as building blocks for the synthesis of other compounds.
In organic chemistry, the Knoevenagel condensation reaction is a type of chemical reaction named after German chemist Emil Knoevenagel. It is a modification of the aldol condensation.
Hexafluoroacetone (HFA) is a chemical compound with the formula (CF3)2CO. It is structurally similar to acetone; however, its reactivity is markedly different. It is a colourless, hygroscopic, nonflammable, highly reactive gas characterized by a musty odour. According to electron diffraction, HFA and acetone adopt very similar structures, the C-O distance being only longer in the fluorinated compound (124.6 vs 121.0 pm), possibly due to steric effects.
Isocrotonic acid (also known as quartenylic acid; formally named (Z)-2-butenoic acid) is the cis isomer of crotonic acid. It is an oil, possessing an odor similar to that of brown sugar. At its boiling point of 171.9 °C, it converts into crotonic acid. The compound can be prepared from 1,3‑dibromo-2‑butanone via the Favorskii rearrangement.
Isonicotinic acid or pyridine-4-carboxylic acid is an organic compound with the formula C5H4N(CO2H). It is a derivative of pyridine with a carboxylic acid substituent at the 4-position. It is an isomer of picolinic acid and nicotinic acid, which have the carboxyl group at the 2- and 3-position respectively compared to the 4-position for isonicotinic acid.
Mucobromic acid is an organic compound that consists of a dibrominated alkene with aldehyde and carboxylic acid functional groups. It easily tautomerizes to a furanone hemiacetal form. This compound, and the analogous mucochloric acid, form the group of known mucohalic acids. The bromide appears to behave similarly to the more heavily studied chloride.
α,β-Unsaturated carbonyl compounds are organic compounds with the general structure (O=CR)−Cα=Cβ−R. Such compounds include enones and enals, but also carboxylic acids and the corresponding esters and amides. In these compounds, the carbonyl group is conjugated with an alkene. Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β-carbon. This pattern of reactivity is called vinylogous. Examples of unsaturated carbonyls are acrolein (propenal), mesityl oxide, acrylic acid, and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction.
Rhizoferrin is an organic compound with the formula (CH2CH2NHCOCH2C(OH)(CO2H)CH2CO2H)2. It is multifunctional molecule with two secondary alcohols, four carboxylic acid groups, and two amide groups. In aqueous solution, it is highly ionized, but the term rhizoferrin is still applied to these species.