Perillartine

• 4 - (1- methylethenyl )-1 -cyclohexene -1 - carbaldehyde
• 1- perillaldehyde - α -oxime
• DL- perillartine
• (±)- perillartine
• Perilla sugar

• 30950-27-7 [ (E, RS)- perillartine ]
• 319907-28-3 [ (S, S)- perillartine ]
• 30674-09-0 [ (Z, RS)- Perillaaldehydoxim ]

Fixed

102 ° C

Slightly soluble in water

2500 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Perillartine is a chiral racemic sweetener, which is the (E)- oxime of the Perillaaldehyds. Its sweetening power is about 2000 times as large as that of sucrose. The water solubility is low, in addition, it has a bitter aftertaste.

As a sweetener, it is mainly used in Japan.

Of perilla aldehyde is the major component of the essential oil of the perilla plant (also called sesame leaf ).

Isomerism

The oxime of Perillaaldehyds has a carbon-nitrogen double bond with (E) - or (Z) configuration. There are also in this molecule is another stereogenic center, the (S) - or (R) -configuration may be. Consequently, the oxime of Perillaaldehyds four stereoisomers: the (S, S) form and its mirror image (S, R) form and the (Z, S) form and the (Z, R)-form. The sweetener is used as perillartine racemate ( 1:1 mixture ) of (S, S) form and the mirror image (S, R)- form.

The (Z, S) form and the (Z, R)-form have no practical significance.

In the scientific literature there are conflicting and confusing information about the structure of formulas and the correct chemical nomenclature of perillartine. Meanwhile, the structural formula was elucidated unambiguously by spectroscopy and by X-ray structural analysis.

SRI oxime V

Oxime V ( engl. SRI oximes V) is a derivative of Perillartins which, although only 450 times sweeter than sucrose, but more water soluble. Oxime V has no undesirable aftertaste and is metabolized easily. Therefore, it will be discussed as an alternative to perillartine.