Pyrroline
Encyclopedia
Pyrrolines, also known under the name dihydropyrroles, are three different heterocyclic
organic
chemical compound
s that differ in the position of the double bond
. Pyrrolines are formally derived from the aromate
pyrrole
by hydrogenation
. 1-Pyrroline is a cyclic imine
, whereas 2-pyrroline and 3-pyrroline are cyclic amine
s.
Heterocyclic compound
A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....
organic
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...
chemical compound
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
s that differ in the position of the double bond
Double bond
A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two. The most common double bond, that between two carbon atoms, can be found in alkenes. Many types of double bonds between two different elements exist, for example in...
. Pyrrolines are formally derived from the aromate
Aromaticity
In organic chemistry, Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. The earliest use of the term was in an article by August...
pyrrole
Pyrrole
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4H4NH. It is a colourless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3...
by hydrogenation
Hydrogenation
Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...
. 1-Pyrroline is a cyclic imine
Imine
An imine is a functional group or chemical compound containing a carbon–nitrogen double bond, with the nitrogen attached to a hydrogen atom or an organic group. If this group is not a hydrogen atom, then the compound is known as a Schiff base...
, whereas 2-pyrroline and 3-pyrroline are cyclic amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
s.
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| 1-Pyrroline | 2-Pyrroline | 3-Pyrroline |
Substituted pyrrolines
- 2-Acetyl-1-pyrroline2-Acetyl-1-pyrroline2-Acetyl-1-pyrroline, abbreviated 2AP, with the IUPAC name 1-ethanone, is an aroma compound and flavor that gives white bread, jasmine rice and basmati rice, the spice pandan , and bread flowers their typical smell...
, an aroma compoundAroma compoundAn aroma compound, also known as odorant, aroma, fragrance or flavor, is a chemical compound that has a smell or odor...
with a white bread-like smell - ThienamycinThienamycinThienamycin, one of the most potent naturally produced antibiotics known thus far, was discovered in Streptomyces cattleya in 1976. Thienamycin has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes.Thienamycin is a zwitterion...
, a beta-lactam antibiotic - MTSLMTSLMTSL is a chemical compound which can be used as a nitroxide paramagnetic spin label in protein Electron paramagnetic resonance spectroscopy experiments. MTSL is attached via a disulfide bond to a cysteine residue, enabling site-directed spin labelling...
, a chemical used for certain NMR experiments - 1-Pyrroline-5-carboxylic acid1-Pyrroline-5-carboxylic acid1-Pyrroline-5-carboxylic acid, also known as 1-pyrroline-5-carboxylate, delta-1-pyrroline-5-carboxylic acid, and P5C, is an imino acid...
, a biosynthetic metabolite - PorphyrinPorphyrinPorphyrins are a group of organic compounds, many naturally occurring. One of the best-known porphyrins is heme, the pigment in red blood cells; heme is a cofactor of the protein hemoglobin. Porphyrins are heterocyclic macrocycles composed of four modified pyrrole subunits interconnected at...
, consisting of two alternating pairs of pyrrol and pyrroline connected via methine (=CH-) bridges
See also
- PyrrolePyrrolePyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4H4NH. It is a colourless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3...
, the aromatic analog with two double bonds - PyrrolidinePyrrolidinePyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula C4H9N. It is a cyclic secondary amine with a five-membered heterocycle containing four carbon atoms and one nitrogen atom...
, the fully saturated analog without double bonds
External links
- Pyrroline, 1-pyrroline, 2-pyrroline, and 3-pyrroline at EMBL-EBI