Perillartine

Structural formula
	( S ) -Perillartin (left) and ( R ) -Perillartin (right)
General
Surname	Perillartine
other names	4- (1-methylethenyl) -1-cyclohexene-1-carbaldehyde oxime; 1-perillaldehyde-α-oxime; DL -perillartin; (±) -Perillartin; Perilla sugar;
Molecular formula	C 10 H 15 NO
External identifiers / databases
EC number	250-402-7
ECHA InfoCard	100.045.806
PubChem	5365782
Wikidata	Q416102
properties
Molar mass	165.23 g · mol -1
Physical state	firmly
Melting point	102 ° C
solubility	slightly soluble in water
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: ?
Toxicological data	2500 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Perillartin is a chiral racemic sweetener that is the ( E ) - oxime of perilla aldehyde . Its sweetening power is about 2,000 times that of sucrose . The water solubility is low and it also has a bitter aftertaste.

It is mainly used as a sweetener in Japan.

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

Isomerism

The oxime of perillaaldehyde has a carbon-nitrogen double bond with an ( E ) or ( Z ) arrangement. In addition, there is another stereogenic center in this molecule that can be ( S ) - or ( R ) -configured. Consequently there are four stereoisomers of the oxime of perillaaldehyde : the ( E , S ) form and the mirror image ( E , R ) form as well as the ( Z , S ) form and the ( Z , R ) form. The sweetener perillartin is used as a racemate (1: 1 mixture) of ( E , S ) form and the mirror image ( E , R ) form.

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

There is conflicting and confusing information about the structural formulas and correct chemical nomenclature of perillartin in the scientific literature. In the meantime, the structural formula has been clarified beyond any doubt by spectroscopy and X-ray structure analysis.

SRI Oxime V

Oxime V

Oxime V ( SRI Oxime V ) is an analogue of perillartin, which is only 450 times sweeter than sucrose, but more soluble in water. Oxime V has no undesirable aftertaste and is easily metabolized . Hence it is being discussed as an alternative to perillartin.

Individual evidence

↑ ^a ^b Susan Budavari (Ed.): The Merck Index . 12th edition. Merck & Co., Whitehouse Station, New Jersey, USA 1996, ISBN 0-911910-12-3 .
↑ ^a ^b H.-D. Belitz et al .: Textbook of Food Chemistry . 5th ed., Springer, Berlin a. a., 2001. p. 433.
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of (E) -4- (1-methylvinyl) cyclohexene-1-carbaldehyde oxime in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on July 10, 2020, is reproduced from a self-classification by distributors .
↑ ^a ^b Lyn O'Brien-Nabors (Ed.): Alternative Sweeteners . Marcel Dekker Inc., 3rd ed. 2001. ISBN 0-8247-0437-1 ; P. 221ff.
^ The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, pp. 7167-7168, ISBN 978-0-911910-00-1 .
↑ EM Acton, H. Stone, MA Leaffer and SM Oliver: Perillartine and Some Derivatives: Clarification of Structures , Cellular and Molecular Life Sciences 26 (1970) 473-474.
↑ RWW Hooft, P. van der Sluis, JA Kanters and J. Kroon: Structure of Racemic 4-Isopropenyl-1-cyclohexene-1-carbaldehyde Oxime (Perillartine) , Acta Crystallographica C46 (1990) 1133-1135.
↑ External identifiers or database links for Oxim V : CAS number: 59691-20-2, PubChem : 9577332 , ChemSpider : 7851769 , Wikidata : Q90570894 .

[merck_index-1] Susan Budavari (Ed.): The Merck Index . 12th edition. Merck & Co., Whitehouse Station, New Jersey, USA 1996, ISBN 0-911910-12-3 .

[Belitz-2] H.-D. Belitz et al .: Textbook of Food Chemistry . 5th ed., Springer, Berlin a. a., 2001. p. 433.

[3] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of (E) -4- (1-methylvinyl) cyclohexene-1-carbaldehyde oxime in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on July 10, 2020, is reproduced from a self-classification by distributors .

[alter-4] Lyn O'Brien-Nabors (Ed.): Alternative Sweeteners . Marcel Dekker Inc., 3rd ed. 2001. ISBN 0-8247-0437-1 ; P. 221ff.

[MerckIndex-5] The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, pp. 7167-7168, ISBN 978-0-911910-00-1 .

[Acton-6] EM Acton, H. Stone, MA Leaffer and SM Oliver: Perillartine and Some Derivatives: Clarification of Structures , Cellular and Molecular Life Sciences 26 (1970) 473-474.

[Hooft-7] RWW Hooft, P. van der Sluis, JA Kanters and J. Kroon: Structure of Racemic 4-Isopropenyl-1-cyclohexene-1-carbaldehyde Oxime (Perillartine) , Acta Crystallographica C46 (1990) 1133-1135.

[8] External identifiers or database links for Oxim V : CAS number: 59691-20-2, PubChem : 9577332 , ChemSpider : 7851769 , Wikidata : Q90570894 .