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Inositol
From Wikipedia, the free encyclopedia
myo-Inositol[1]
myo-Inositol
myo-Inositol
IUPAC name[hide]
(1R,2R,3S,4S,5R,6S)-cyclohexane-1,2,3,4,5,6-hexol
Other names[hide]
cis-1,2,3,5-trans-4,6-Cyclohexanehexol , Cyclohexanehexol,
Mouse antialopecia factor,
Nucite, Phaseomannite,
Phaseomannitol,
Rat antispectacled eye
factor, and Scyllite
(for the structural
isomer scyllo-Inositol)
Identifiers
CAS number 87-89-8 Yes
PubChem 892
ChemSpider 10239179 Yes
UNII 4L6452S749 Yes
KEGG D08079 Yes
ChEBI CHEBI:17268 Yes
ChEMBL CHEMBL1222251 Yes
ATC code A11HA07
Jmol-3D images Image 1
SMILES
[show]
InChI
[show]
Properties
Molecular formula C6H12O6
Molar mass 180.16 g mol−1
Density 1.752 g/cm³
Melting point 225–227 °C
Hazards
NFPA 704
NFPA 704 four-colored diamond
010
Flash point 143 °C (289 °F; 416 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Yes (verify) (what is: Yes/?)
Infobox references
Inositol or cyclohexane-1,2,3,4,5,6-hexol is a chemical compound with formula C6H12O6 or (-CHOH-)6, a sixfold alcohol (polyol) of cyclohexane. It exists in nine possible stereoisomers, of which the most prominent form, widely occurring in nature, is cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol (former names meso-inositol or i-inositol).[2][3] Inositol is a carbohydrate, though not a classical sugar. It has a taste which has been assayed at half the sweetness of table sugar (sucrose).[4][5]
myo-Inositol plays an important role as the structural basis for a number of secondary messengers in eukaryotic cells, the various inositol phosphates. In addition, inositol serves as an important component of the structural lipids phosphatidylinositol (PI) and its various phosphates, the phosphatidylinositol phosphate (PIP) lipids.
Inositol or its phosphates and associated lipids are found in many foods, in particular fruit, especially cantaloupe and oranges.[6] In plants, the hexaphosphate of inositol, phytic acid or its salts, the phytates, are found. These serve as phosphate stores in the seed. Phytic acid occurs also in cereals with high bran content and also nuts and beans, but inositol when present as phytate is not directly bioavailable to humans in the diet, since it is not digestible (s)ome food preparation techniques partly break down phytates to change this. Inositol as it occurs in certain plant-derived substances such as lecithins, however, is well-absorbed and relatively bioavailable.
myo-Inositol (free of phosphate) was once considered a member of the vitamin B complex; however, because it is produced by the human body from glucose, it is not an essential nutrient.[7] Some substances such as niacin can also be synthesized in the body, but are not made in amounts considered adequate for good health, and thus are still classified as essential nutrients. However, there is no convincing evidence that this is the case for myo-inositol.
Contents [hide]
1 Isomers and structure
2 Synthesis
3 Function
3.1 Phytic acid in plants
4 Explosive potential
5 Counter to road salt
6 Clinical applications
6.1 Psychiatric conditions
6.2 Other conditions
7 Common use as a "cutting" agent
8 Nutritional sources
9 See also
10 References
11 External links
Isomers and structure[edit]
The isomer myo-inositol is a meso compound possessing an optically inactive plane of symmetry through the molecule, and meso-inositol is an obsolete name that refers to myo-inositol. Besides myo-inositol, the other naturally occurring stereoisomers (though in minimal quantities) are scyllo-, muco-, D-chiro-, and neo-inositol. The other possible isomers are L-chiro-, allo-, epi-, and cis-inositol. As their name denotes, the two chiro inositols are the only pair of inositol enantiomers, but they are enantiomers of each other, not of myo-inositol.
Myo-inositol.svg Scyllo-inositol.svg Muco-inositol.svg Chiro-inositol.svg
myo- scyllo- muco- chiro-
Neo-inositol.svg Allo-inositol.svg Epi-inositol.svg
Cis-inositol.svg
neo- allo- epi- cis-
In its most stable conformational geometry, the myo-inositol isomer assumes the chair conformation, which puts the maximum number of hydroxyls to the equatorial position, where they are farthest apart from each other. In this conformation the natural myo isomer has a structure in which five of the six hydroxyls (the 1st, 3rd, 4th, 5th, and 6th) are equatorial, whereas the 2nd hydroxyl group is axial.[8]
Synthesis[edit]
myo-Inositol is synthesized from glucose-6-phosphate (G-6-P) in two steps. First, G-6-P is isomerised by an inositol-3-phosphate synthase enzyme (called ISYNA1) to myo-inositol 1-phosphate, which is then dephosphorylated by an inositol monophosphatase enzyme (called IMPase 1) to give free myo-inositol. In humans most inositol is synthesized in the kidneys, in typical amounts of a few grams per day.[9]
Function[edit]
Inositol and some of its mono and polyphosphates function as the basis for a number of signaling and secondary messenger molecules. They are involved in a number of biological processes, including:
Insulin signal transduction[10]
Cytoskeleton assembly
Nerve guidance (Epsin)
Intracellular calcium (Ca2+) concentration control[11]
Cell membrane potential maintenance[12]
Breakdown of fats [13]
Gene expression[14][15]
Phytic acid in plants[edit]
Phytic acid, which is inositol hexakisphosphate (IP6), also known as phytate when in salt form, is the principal storage form of phosphorus in many plant tissues, especially bran and seeds.[16] Neither the inositol nor the phosphate in phytic acid in plants is available to humans, or to animals that are not ruminants, since it cannot be broken down, except by bacteria. Moreover, phytic acid also chelates important minerals such as calcium, magnesium, iron, and zinc, making them unabsorbable, and contributing to mineral deficiencies in people whose diets rely highly on bran and seeds for their mineral intake, such as occurs in developing countries.[17][18]
Inositol penta- (IP5), tetra- (IP4), and triphosphate (IP3) are also called "phytates."
Explosive potential[edit]
At the 1936 meeting of the American Chemical Society, professor Edward Bartow of the University of Iowa presented a commercially viable means of extracting large amounts of inositol from the phytic acid naturally present in waste corn. As a possible use for the chemical, he suggested inositol nitrate as a more stable alternative to nitroglycerin.[19] Today, inositol nitrate is used to gelatinize nitrocellulose, and thus can be found in many modern explosives and solid rocket propellants.[20]
Counter to road salt[edit]
When plants are exposed to increasing concentrations of road salt, the plant cells become dysfunctional, and commit apoptosis, leading to an inhibition of growth in plants. Inositol pretreatment could reverse the effects of salt on plants.
Clinical applications[edit]
Psychiatric conditions[edit]
Some preliminary results of studies on high-dose inositol supplements show promising results for people suffering from problems such as bulimia, panic disorder, obsessive-compulsive disorder (OCD), agoraphobia, and unipolar and bipolar depression.[21][22][23]
Eur Neuropsychopharmacol. 1997 May;7(2):147-55.
In a single double-blind study on 13 patients, myo-inositol (18 grams daily) has been found to reduce the symptoms of OCD significantly, with effectiveness equal to SSRIs and virtually without side-effects.[24] In a double-blind, controlled trial, myo-inositol (18 grams daily) was superior to fluvoxamine for decreasing the number of panic attacks and other side-effects.[21]
A double-blind, placebo-controlled study of depressed patients showed that a high dose of inositol (12 grams daily) resulted in significant improvement of symptoms, with no changes noted in liver, kidney, or hematological function.[22] A meta-analysis that included only four randomized trials of inositol for depression could not determine whether or not inositol is of benefit for depression. However, in addition to studies against placebo, the meta-analysis included only four trials and took the unusual steps of contacting pharmaceutical companies for any unpublishable studies to include, and of including studies comparing the effect of inositol against known effective treatments, without placebo. The studies of the latter type were larger and had more weight. [25]
Other studies suggest that lithium treatment may further inhibit the enzyme inositol monophosphatase, leading to higher intracellular levels of inositol triphosphate,[26] an effect that was enhanced further by administration of an inositol triphosphate reuptake inhibitor.
Other conditions[edit]
D-chiro-Inositol (DCI) has been found in two double-blind studies to be an effective treatment for many of the clinical hallmarks of polycystic ovary syndrome (PCOS), including insulin resistance, hyperandrogenism, and oligo-amenorrhea;[27][28] the impetuses for these studies were the observed defects in DCI metabolism in PCOS and the implication of DCI in insulin signal transduction.[10][29] Another small, placebo-controlled study has demonstrated that myo-inositol supplementation improves features of dysmetabolic syndrome in post-menopausal women, including triglycerides, HDL cholesterol, and diastolic blood pressure.[30]
Animal studies suggest inositol reduces the severity of the osmotic demyelination syndrome if given before rapid correction of chronic hyponatraemia.[31] Further study is required before its application in humans for this indication.
Studies from in vitro experiments, animal studies, and limited clinical experiences, claim that inositol may be used effectively against some types of cancer, in particular, when used in combination with phytic acid.[32]
Common use as a "cutting" agent[edit]
Inositol has been used as an adulterant (or cutting agent) in many illegal drugs, such as cocaine, methamphetamine, and sometimes heroin.[33] It is presumed that this use is connected with one or more of the substance's properties of solubility, powdery texture, or reduced sweetness (50%) as compared with more common sugars.
Inositol is also used as a stand-in for cocaine on television.[34]
Nutritional sources[edit]
myo-Inositol is naturally present in a variety of foods, although tables of this do not always distinguish between the bioavailable lecithin form, and the non-available phytate form in grains.[35] According to research, foods containing the highest concentrations of myo-inositol (including its compounds) include fruits, beans, grains and nuts.[35] Beans and grains, however, as seeds, contain large amounts of inositol as phytate.
See also[edit]
From Wikipedia, the free encyclopedia
myo-Inositol[1]
myo-Inositol
myo-Inositol
IUPAC name[hide]
(1R,2R,3S,4S,5R,6S)-cyclohexane-1,2,3,4,5,6-hexol
Other names[hide]
cis-1,2,3,5-trans-4,6-Cyclohexanehexol , Cyclohexanehexol,
Mouse antialopecia factor,
Nucite, Phaseomannite,
Phaseomannitol,
Rat antispectacled eye
factor, and Scyllite
(for the structural
isomer scyllo-Inositol)
Identifiers
CAS number 87-89-8 Yes
PubChem 892
ChemSpider 10239179 Yes
UNII 4L6452S749 Yes
KEGG D08079 Yes
ChEBI CHEBI:17268 Yes
ChEMBL CHEMBL1222251 Yes
ATC code A11HA07
Jmol-3D images Image 1
SMILES
[show]
InChI
[show]
Properties
Molecular formula C6H12O6
Molar mass 180.16 g mol−1
Density 1.752 g/cm³
Melting point 225–227 °C
Hazards
NFPA 704
NFPA 704 four-colored diamond
010
Flash point 143 °C (289 °F; 416 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Yes (verify) (what is: Yes/?)
Infobox references
Inositol or cyclohexane-1,2,3,4,5,6-hexol is a chemical compound with formula C6H12O6 or (-CHOH-)6, a sixfold alcohol (polyol) of cyclohexane. It exists in nine possible stereoisomers, of which the most prominent form, widely occurring in nature, is cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol (former names meso-inositol or i-inositol).[2][3] Inositol is a carbohydrate, though not a classical sugar. It has a taste which has been assayed at half the sweetness of table sugar (sucrose).[4][5]
myo-Inositol plays an important role as the structural basis for a number of secondary messengers in eukaryotic cells, the various inositol phosphates. In addition, inositol serves as an important component of the structural lipids phosphatidylinositol (PI) and its various phosphates, the phosphatidylinositol phosphate (PIP) lipids.
Inositol or its phosphates and associated lipids are found in many foods, in particular fruit, especially cantaloupe and oranges.[6] In plants, the hexaphosphate of inositol, phytic acid or its salts, the phytates, are found. These serve as phosphate stores in the seed. Phytic acid occurs also in cereals with high bran content and also nuts and beans, but inositol when present as phytate is not directly bioavailable to humans in the diet, since it is not digestible (s)ome food preparation techniques partly break down phytates to change this. Inositol as it occurs in certain plant-derived substances such as lecithins, however, is well-absorbed and relatively bioavailable.
myo-Inositol (free of phosphate) was once considered a member of the vitamin B complex; however, because it is produced by the human body from glucose, it is not an essential nutrient.[7] Some substances such as niacin can also be synthesized in the body, but are not made in amounts considered adequate for good health, and thus are still classified as essential nutrients. However, there is no convincing evidence that this is the case for myo-inositol.
Contents [hide]
1 Isomers and structure
2 Synthesis
3 Function
3.1 Phytic acid in plants
4 Explosive potential
5 Counter to road salt
6 Clinical applications
6.1 Psychiatric conditions
6.2 Other conditions
7 Common use as a "cutting" agent
8 Nutritional sources
9 See also
10 References
11 External links
Isomers and structure[edit]
The isomer myo-inositol is a meso compound possessing an optically inactive plane of symmetry through the molecule, and meso-inositol is an obsolete name that refers to myo-inositol. Besides myo-inositol, the other naturally occurring stereoisomers (though in minimal quantities) are scyllo-, muco-, D-chiro-, and neo-inositol. The other possible isomers are L-chiro-, allo-, epi-, and cis-inositol. As their name denotes, the two chiro inositols are the only pair of inositol enantiomers, but they are enantiomers of each other, not of myo-inositol.
Myo-inositol.svg Scyllo-inositol.svg Muco-inositol.svg Chiro-inositol.svg
myo- scyllo- muco- chiro-
Neo-inositol.svg Allo-inositol.svg Epi-inositol.svg
Cis-inositol.svg
neo- allo- epi- cis-
In its most stable conformational geometry, the myo-inositol isomer assumes the chair conformation, which puts the maximum number of hydroxyls to the equatorial position, where they are farthest apart from each other. In this conformation the natural myo isomer has a structure in which five of the six hydroxyls (the 1st, 3rd, 4th, 5th, and 6th) are equatorial, whereas the 2nd hydroxyl group is axial.[8]
Synthesis[edit]
myo-Inositol is synthesized from glucose-6-phosphate (G-6-P) in two steps. First, G-6-P is isomerised by an inositol-3-phosphate synthase enzyme (called ISYNA1) to myo-inositol 1-phosphate, which is then dephosphorylated by an inositol monophosphatase enzyme (called IMPase 1) to give free myo-inositol. In humans most inositol is synthesized in the kidneys, in typical amounts of a few grams per day.[9]
Function[edit]
Inositol and some of its mono and polyphosphates function as the basis for a number of signaling and secondary messenger molecules. They are involved in a number of biological processes, including:
Insulin signal transduction[10]
Cytoskeleton assembly
Nerve guidance (Epsin)
Intracellular calcium (Ca2+) concentration control[11]
Cell membrane potential maintenance[12]
Breakdown of fats [13]
Gene expression[14][15]
Phytic acid in plants[edit]
Phytic acid, which is inositol hexakisphosphate (IP6), also known as phytate when in salt form, is the principal storage form of phosphorus in many plant tissues, especially bran and seeds.[16] Neither the inositol nor the phosphate in phytic acid in plants is available to humans, or to animals that are not ruminants, since it cannot be broken down, except by bacteria. Moreover, phytic acid also chelates important minerals such as calcium, magnesium, iron, and zinc, making them unabsorbable, and contributing to mineral deficiencies in people whose diets rely highly on bran and seeds for their mineral intake, such as occurs in developing countries.[17][18]
Inositol penta- (IP5), tetra- (IP4), and triphosphate (IP3) are also called "phytates."
Explosive potential[edit]
At the 1936 meeting of the American Chemical Society, professor Edward Bartow of the University of Iowa presented a commercially viable means of extracting large amounts of inositol from the phytic acid naturally present in waste corn. As a possible use for the chemical, he suggested inositol nitrate as a more stable alternative to nitroglycerin.[19] Today, inositol nitrate is used to gelatinize nitrocellulose, and thus can be found in many modern explosives and solid rocket propellants.[20]
Counter to road salt[edit]
When plants are exposed to increasing concentrations of road salt, the plant cells become dysfunctional, and commit apoptosis, leading to an inhibition of growth in plants. Inositol pretreatment could reverse the effects of salt on plants.
Clinical applications[edit]
Psychiatric conditions[edit]
Some preliminary results of studies on high-dose inositol supplements show promising results for people suffering from problems such as bulimia, panic disorder, obsessive-compulsive disorder (OCD), agoraphobia, and unipolar and bipolar depression.[21][22][23]
Eur Neuropsychopharmacol. 1997 May;7(2):147-55.
In a single double-blind study on 13 patients, myo-inositol (18 grams daily) has been found to reduce the symptoms of OCD significantly, with effectiveness equal to SSRIs and virtually without side-effects.[24] In a double-blind, controlled trial, myo-inositol (18 grams daily) was superior to fluvoxamine for decreasing the number of panic attacks and other side-effects.[21]
A double-blind, placebo-controlled study of depressed patients showed that a high dose of inositol (12 grams daily) resulted in significant improvement of symptoms, with no changes noted in liver, kidney, or hematological function.[22] A meta-analysis that included only four randomized trials of inositol for depression could not determine whether or not inositol is of benefit for depression. However, in addition to studies against placebo, the meta-analysis included only four trials and took the unusual steps of contacting pharmaceutical companies for any unpublishable studies to include, and of including studies comparing the effect of inositol against known effective treatments, without placebo. The studies of the latter type were larger and had more weight. [25]
Other studies suggest that lithium treatment may further inhibit the enzyme inositol monophosphatase, leading to higher intracellular levels of inositol triphosphate,[26] an effect that was enhanced further by administration of an inositol triphosphate reuptake inhibitor.
Other conditions[edit]
D-chiro-Inositol (DCI) has been found in two double-blind studies to be an effective treatment for many of the clinical hallmarks of polycystic ovary syndrome (PCOS), including insulin resistance, hyperandrogenism, and oligo-amenorrhea;[27][28] the impetuses for these studies were the observed defects in DCI metabolism in PCOS and the implication of DCI in insulin signal transduction.[10][29] Another small, placebo-controlled study has demonstrated that myo-inositol supplementation improves features of dysmetabolic syndrome in post-menopausal women, including triglycerides, HDL cholesterol, and diastolic blood pressure.[30]
Animal studies suggest inositol reduces the severity of the osmotic demyelination syndrome if given before rapid correction of chronic hyponatraemia.[31] Further study is required before its application in humans for this indication.
Studies from in vitro experiments, animal studies, and limited clinical experiences, claim that inositol may be used effectively against some types of cancer, in particular, when used in combination with phytic acid.[32]
Common use as a "cutting" agent[edit]
Inositol has been used as an adulterant (or cutting agent) in many illegal drugs, such as cocaine, methamphetamine, and sometimes heroin.[33] It is presumed that this use is connected with one or more of the substance's properties of solubility, powdery texture, or reduced sweetness (50%) as compared with more common sugars.
Inositol is also used as a stand-in for cocaine on television.[34]
Nutritional sources[edit]
myo-Inositol is naturally present in a variety of foods, although tables of this do not always distinguish between the bioavailable lecithin form, and the non-available phytate form in grains.[35] According to research, foods containing the highest concentrations of myo-inositol (including its compounds) include fruits, beans, grains and nuts.[35] Beans and grains, however, as seeds, contain large amounts of inositol as phytate.
See also[edit]