Names | |
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IUPAC name 1D-chiro-Inositol | |
Systematic IUPAC name (1R,2S,3R,4S,5S,6S)-6-Methoxycyclohexane-1,2,3,4,5-pentol | |
Other names 3-O-Methyl-D-chiro-inositol D-(+)-chiro-Inositol D-Pinitol Inzitol D-(+)-Pinitol (+)-Pinitol Sennitol Pinnitol | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C7H14O6 | |
Molar mass | 194.183 g·mol−1 |
Melting point | 179 to 185 °C (354 to 365 °F; 452 to 458 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Pinitol is a cyclitol, a cyclic polyol. It is a known anti-diabetic agent isolated from Sutherlandia frutescens leaves. [1] [2] Gall plant tannins can be differentiated by their content of pinitol. [3] It was first identified in the sugar pine ( Pinus lambertiana ). [4] It is also found in other plants, such as in the pods of the carob tree. [5]
Certain variants of the bacteria Pseudomonas putida have been used in organic synthesis, the first example being the oxidation of benzene, employed by Steven Ley in the synthesis of (±)-pinitol. [6]
Ciceritol is a pinitol digalactoside that can be isolated from seeds of chickpea, lentil and white lupin. [7]
A cyclitol derivative can be found in the marine sponge Petrosia sp. [8]
D-pinitol is the most widely distributed inositol ether in plants. [9] In Angiosperms, D-pinitol has a relatively straight forward and short biosynthesis which proceeds via the Loewus pathway. The precursor to the biosynthesis pathway is glucose-6-phosphate, which is converted to D-ononitol (1-D-4-O-methyl-myo-inositol) via myo-inositol. Ononitol is epimerized to yield D-pinitol via a D-ononitol epimerase using NADPH as a cofactor. [10]
Porphyrins are a group of heterocyclic macrocycle organic compounds, composed of four modified pyrrole subunits interconnected at their α carbon atoms via methine bridges (=CH−). In vertebrates, an essential member of the porphyrin group is heme, which is a component of hemoproteins, whose functions include carrying oxygen in the bloodstream. In plants, an essential porphyrin derivative is chlorophyll, which is involved in light harvesting and electron transfer in photosynthesis.
Inositol, primarily the isomer myo-inositol, is a carbocyclic sugar that is abundant in the brain and other mammalian tissues; it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and participates in osmoregulation. Concerning regulation of osmosis, in most mammalian cells the intracellular concentrations of myo-inositol are 5 to 500 times greater than the extracellular concentrations.
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone.
Quinic acid is a cyclitol, a cyclic polyol, and a cyclohexanecarboxylic acid. It is a colorless solid that can be extracted from plant sources. Quinic acid is implicated in the perceived acidity of coffee.
The polyol pathway is a two-step process that converts glucose to fructose. In this pathway glucose is reduced to sorbitol, which is subsequently oxidized to fructose. It is also called the sorbitol-aldose reductase pathway.
β-sitosterol (beta-sitosterol) is one of several phytosterols with chemical structures similar to that of cholesterol. It is a white, waxy powder with a characteristic odor, and is one of the components of the food additive E499. Phytosterols are hydrophobic and soluble in alcohols.
Inositol oxygenase, also commonly referred to as myo-inositol oxygenase (MIOX), is a non-heme di-iron enzyme that oxidizes myo-inositol to glucuronic acid. The enzyme employs a unique four-electron transfer at its Fe(II)/Fe(III) coordination sites and the reaction proceeds through the direct binding of myo-inositol followed by attack of the iron center by diatomic oxygen. This enzyme is part of the only known pathway for the catabolism of inositol in humans and is expressed primarily in the kidneys. Recent medical research regarding MIOX has focused on understanding its role in metabolic and kidney diseases such as diabetes, obesity and acute kidney injury. Industrially-focused engineering efforts are centered on improving MIOX activity in order to produce glucaric acid in heterologous hosts.
The Rubottom oxidation is a useful, high-yielding chemical reaction between silyl enol ethers and peroxyacids to give the corresponding α-hydroxy carbonyl product. The mechanism of the reaction was proposed in its original disclosure by A.G. Brook with further evidence later supplied by George M. Rubottom. After a Prilezhaev-type oxidation of the silyl enol ether with the peroxyacid to form the siloxy oxirane intermediate, acid-catalyzed ring-opening yields an oxocarbenium ion. This intermediate then participates in a 1,4-silyl migration to give an α-siloxy carbonyl derivative that can be readily converted to the α-hydroxy carbonyl compound in the presence of acid, base, or a fluoride source.
In enzymology, an inositol-3-phosphate synthase is an enzyme that catalyzes the chemical reaction
The enzyme Inositol phosphate-phosphatase is of the phosphodiesterase family of enzymes. It is involved in the phosphophatidylinositol signaling pathway, which affects a wide array of cell functions, including but not limited to, cell growth, apoptosis, secretion, and information processing. Inhibition of inositol monophosphatase may be key in the action of lithium in treating bipolar disorder, specifically manic depression.
In enzymology, 1-phosphatidylinositol-4-phosphate 5-kinase is an enzyme that catalyzes the chemical reaction
Inositol monophosphatase 1 is an enzyme that in humans is encoded by the IMPA1 gene.
Pancratistatin (PST) is a natural compound initially extracted from spider lily, a Hawaiian native plant of the family Amaryllidaceae (AMD).
The aminocyclitols are compounds related to cyclitols. They possess features of relative and absolute configuration that are characteristic of their class and have been extensively studied; but these features are not clearly displayed by general methods of stereochemical nomenclature, so that special methods of specifying their configuration are justified and have long been used. In other than stereochemical respects, their nomenclature should follow the general rules of organic chemistry.
In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is C
nH
2n-x(OH)
x or C
nH
2nO
x where 3 ≤ x ≤ n.
5-Deoxyinositol (quercitol) is a cyclitol. It can be found in wines aged in oak wood barrels. It can also be found in Quercus sp. (oaks) and in Gymnema sylvestre. It is different from quercetol, a synonym of quercetin.
Bornesitol is a cyclitol. It can be found in the gentianaceae and menyanthaceae plant families. Chemically, it is a methyl ether of D-myo-inositol.
Ciceritol is a cyclitol. It is a pinitol digalactoside that can be isolated from seeds of chickpea, lentil and white lupin.
1,2,3,4,5-Cyclopentanepentol, also named cyclopentane-1,2,3,4,5-pentol or 1,2,3,4,5-pentahydroxycyclopentane is a chemical compound with formula C
5H
10O
5 or (–CHOH–)
5, whose molecule consists of a ring of five carbon atoms, each connected to one hydrogen and one hydroxyl group. The unqualified term "cyclopentanepentol" usually refers to this compound. There are four distinct stereoisomers with this same structure.
Erythrina alkaloids, generally containing benzyl-tetrahydroisoquinoline structure, are widely distributed in Erythrina species, a genus of plants which belong to the Fabaceae family in tropical and subtropical regions. The Erythrina alkaloids can be found in several organs of Erythrina trees but are primarily found in their seeds. They display several unique properties, and are the subject of active scientific research relating to their synthesis and bioactivity.