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74134

Sigma-Aldrich

epi-Inositol

≥98.0% (HPLC)

Synonym(s):

epi-Cyclohexanehexol

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About This Item

Empirical Formula (Hill Notation):
C6H12O6
CAS Number:
Molecular Weight:
180.16
EC Number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

Assay

≥98.0% (HPLC)

form

crystals

storage temp.

2-8°C

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-NIPYSYMMSA-N

Biochem/physiol Actions

epi-Inositol has regulatory effects on expression of the most highly regulated gene in the inositol biosynthetic pathway.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Akari Ozaki et al.
Journal of bioscience and bioengineering, 109(4), 337-340 (2010-03-17)
Phospholipase D-mediated synthesis of phosphatidylinositols having various inositol stereoisomers was studied. Seven inositol stereoisomers were tested, all of which were found to be substrates of the enzyme, generating the corresponding phosphatidylinositols. Based on the substrate specificity, models for the recognition
A Shaldubina et al.
Molecular psychiatry, 7(2), 174-180 (2002-02-13)
Myo-inositol exerts behavioral effects in animal models of psychiatric disorders and is effective in clinical trials in psychiatric patients. Interestingly, epi-inositol exerts behavioral effects similar to myo-inositol, even though epi-inositol is not a substrate for synthesis of phosphatidylinositol. We postulated
Xiao-Long Liu et al.
Pesticide biochemistry and physiology, 164, 7-13 (2020-04-15)
Insect gustatory system plays important roles in multiple behaviors including feeding, mating, and oviposition. Gustatory receptors (GRs), located on the dendritic membrane of gustatory sensory neurons (GSNs), are crucial in peripheral coding of non-volatile compounds. However, GRs and their detailed
J McLaurin et al.
The Journal of biological chemistry, 275(24), 18495-18502 (2000-04-15)
Inositol has 8 stereoisomers, four of which are physiologically active. myo-Inositol is the most abundant isomer in the brain and more recently shown that epi- and scyllo-inositol are also present. myo-Inositol complexes with Abeta42 in vitro to form a small
JoAnne McLaurin et al.
Nature medicine, 12(7), 801-808 (2006-06-13)
When given orally to a transgenic mouse model of Alzheimer disease, cyclohexanehexol stereoisomers inhibit aggregation of amyloid beta peptide (Abeta) into high-molecular-weight oligomers in the brain and ameliorate several Alzheimer disease-like phenotypes in these mice, including impaired cognition, altered synaptic

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