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I5125

Sigma-Aldrich

myo-Inositol

≥99% (GC), powder, precursor of membrane phospho-inositides and phospholipid

Synonym(s):

1,2,3,4,5,6-Hexahydroxycyclohexane, i-Inositol, meso-Inositol

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About This Item

Empirical Formula (Hill Notation):
C6H12O6
CAS Number:
Molecular Weight:
180.16
Beilstein:
1907329
EC Number:
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:
NACRES:
NA.77

product name

myo-Inositol, ≥99%

vapor density

6.2 (vs air)

Quality Level

Assay

≥99%

mp

222-227 °C (lit.)

solubility

H2O: 50 mg/mL

SMILES string

O[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-

InChI key

CDAISMWEOUEBRE-GPIVLXJGSA-N

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General description

myo-Inositol (MI) is a sugar-like molecule, found primarily in the glial cells of human brain. It is a stereoisomer of a C6 sugar alcohol, which is part of the inositol family. It serves as the precursor of inositol triphosphate, and as an intracellular second messenger. Myo-inositol regulates several hormones like thyroid-stimulating hormone, follicle-stimulating hormone (FSH), and insulin. Myo-inositol and d-chiro-inositol, which is another stereoisomeric form of inositol, contribute to balancing various metabolic deregulations associated with insulin resistance (IR) in different ways.

Application

myo-Inositol has been used:
  • as a standard for monosaccharide analysis by gas-liquid chromatography (GC)
  • as a component of R-free seahorse media for cultivation of peritoneal macrophages (PMΦs) to study cellular glycolytic metabolism
  • as a SOFaaci media supplement for extending in vitro embryo growth
  • as a component of α minimum essential medium (αMEM) complete media to culture natural killer (NK) cell line

Biochem/physiol Actions

myo-Inositol (MI) serves as an osmolyte and is an important precursor of membrane phospho-inositides and phospholipids. It aids in the formation of the cell membrane and myelin sheet structures. Increased concentration of myo-Inositol (MI) is observed in various brain disorders such as Alzheimer′s disease, gliomatosis cerebri, and brain tumors.
A component of membrane phospholipids, glycosyl­phosphatidyl­inositol anchors that bind glycoproteins to cell membranes, and inositol phosphate second messengers.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hiroki Okada et al.
STAR protocols, 2(3), 100733-100733 (2021-08-31)
Microscopy-based analysis of protein accumulation at a given subcellular location in real time provides invaluable insights into the function of a protein in a specific process. Here, we describe a detailed protocol for determining protein accumulation kinetics at the division
Satu Hänninen et al.
Bio-protocol, 7(9), e2268-e2268 (2017-05-05)
Glycerophospholipids consist of a glycerophosphate backbone to which are esterified two acyl chains and a polar head group. The head group (e.g., choline, ethanolamine, serine or inositol) defines the glycerophospholipid class, while the acyl chains together with the head group
Carmen G Palii et al.
Cell stem cell, 24(5), 812-820 (2019-03-19)
Hematopoiesis provides an accessible system for studying the principles underlying cell-fate decisions in stem cells. Proposed models of hematopoiesis suggest that quantitative changes in lineage-specific transcription factors (LS-TFs) underlie cell-fate decisions. However, evidence for such models is lacking as TF
M Utriainen et al.
Journal of neuro-oncology, 62(3), 329-338 (2003-06-05)
The signal of choline containing compounds (Cho) in proton magnetic resonance spectroscopy (1H-MRS) is elevated in brain tumors. [11C]choline uptake as assessed using positron emission tomography (PET) has also been suggested to be higher in brain tumors than in the
Pascal M Groenen et al.
American journal of obstetrics and gynecology, 189(6), 1713-1719 (2004-01-08)
The purpose of this study was to investigate the maternal and children's myo-inositol, glucose, and zinc status in association with spina bifida risk. Sixty-three mothers and 70 children with spina bifida and 102 control mothers and 85 control children were

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