Inositol

• Cyclohexanhexol
• Inositol

A11HA07, A05BA08 ( myo -inositol )

White, crystalline, odorless solid with a sweet taste

Fixed

1.75 g · cm -3

223-225 ° C

Readily soluble in water: 250 g · l-1 (20 ° C)

10,000 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Inositol ( the inositol; well, especially in Engl: inositol; outdated " muscle sugar ") is the common name for Cyclohexanhexol, a hexavalent cyclic alcohol. Depending on the position of the hydroxyl groups of nine stereoisomers are possible, including a pair of enantiomers ( chiro -inositol ). In the most common form in nature, the hydroxy groups on the carbon atoms 1, 2, 3 and 5 on the same side of the ring and the hydroxyl groups at C4 and C6 of the opposite side. This form carries the systematic name cyclohexane -cis -1 ,2,3,5 -trans -4 ,6- hexol, the trivial names myo- inositol and is found in many animal and plant tissues.

The trivial names of the other isomers are rare: scyllo -, D -chiro-, L -chiro-, muco -, neo -, allo -, epi - and cis- inositol.

All isomers have a sweetish taste.

Although inositol bears the common name " muscle sugar ", it is not, this is a carbohydrate because it has no carbonyl group and therefore can not form a cyclic hemiacetal. He only met the original criteria of a carbon hydrate ( hydrated carbon), namely that its molecular formula Cn (H2O ) n and that inositol is an isomer (the same empirical formula ) to glucose and fructose.

The actually derived from the Anglo- American language variant inositol has become the norm in the natural sciences, especially in compound words it is by far the more common variant.

Occurrence and significance

In the body, usually occurs inositol phosphates on esterified. He was formerly associated with the B vitamins, but the vitamin effect is controversial today. For micro- inositol acts as a growth factor and is designated there as I Bios. In almost all higher plants it occurs as a component of sphingolipids. In fungi, bacteria and some higher plants, the alcohol is found mainly as phytic acid ( inositolhexaphosphoric ) for phosphate storage.

Second messenger

The 1D -myo -inositol -1 ,4,5- trisphosphate (Simplified inositol triphosphate, IP3 ) plays as a second messenger in signal transduction in cells play an important role. It is determined by phospholipase mediated hydrolytic cleavage of the phospholipid phosphatidylinositol -4 ,5- bisphosphate ( PIP2 ) - releases - having a 1,2- diacylglycerol (DAG) and just IP3. IP3 is able to affect the cellular metabolism, it causes, for example, the rise in Ca2 concentration in the cell.

See also:

• Signaling pathways of insulin
• Inositol- 1 ,4,5 -triphosphate ( IP3) as a second messenger
• Function of the phospholipase C, protein kinase C signal transduction in
• Endoplasmic reticulum as a calcium storage

Extraction

Myo -inositol is obtained by hydrolysis of phytic acid from corn steep liquor is again isolatable:

Use

Inositol is commercially available as a dietary supplement for humans or horses. Due to its visual similarity, the easy availability and low price Inositpulver is often used for the stretching of cocaine or N-methyl amphetamine. It is also found in various energy drinks.