Hernandulcin

Structural formula
General
Surname	Hernandulcin
other names	6- (1,5-dimethyl-1-hydroxy-hex-4-enyl) -3-methyl-cyclohex-2-enone; (6 S ) -6 - [(2 S ) -2-Hydroxy-6-methylhept-5-en-2-yl] -3-methylcyclohex-2-en-1-one ( IUPAC ); (6 S , 1 ' S ) -6- (1'-Hydroxy-1', 5'-dimethyl-4'-hexenyl) -3-methyl-2-cyclohexenone;
Molecular formula	C 15 H 24 O 2
External identifiers / databases
PubChem	125608
Wikidata	Q418686
properties
Molar mass	236.35 g mol −1
boiling point	130–140 ° C (at 0.12 h Pa )
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hernandulcin is a sweet tasting sesquiterpene that is found in the Aztec sweet herb (Lippia dulcis) .

Occurrence

Hernandulcin was isolated as a colorless, oily substance from the Aztec sweet herb and named after the Spanish doctor Francisco Hernández , who was the first to describe the Aztec sweet herb in 1570.

properties

The sweetness of hernandulcine compared to sucrose is 1,250 in a 0.25 molar solution . The sweet taste is slightly less pleasant than that of sucrose and is accompanied by a bitter aftertaste.

The specific rotation value of the natural (+) - hernandulcin is + 126 ° (c = 0.113 in ethanol at 22 ° C ).

After synthesis of all stereoisomers it was found that only the natural (+) - hernandulcin with (2 S , 6 S ) -configuration tastes sweet. All other non-natural stereoisomers only taste bitter.

Manufacturing

In the meantime it has been possible to synthesize (+) - hernandulcin in an enantiospecific manner .

Individual evidence

↑ ^a ^b ^c Kenji Mori; Minoru Kato: Synthesis of (6S, 1'S) - (+) - Hernandulcin, a sweetner and its stereoisomers , Tetrahedron 42, 5895-5900, 1986.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Jung Hun Kima; Hyun Jin Lima; Seung Hoon Cheon: Synthesis of (+) - hernandulcin and (+) - epihernandulcin , Tetrahedron Letters 43, 4721-4722, 2002 doi : 10.1016 / S0040-4039 (02) 00939-5 .

literature

H.-D. Belitz et al .: Textbook of Food Chemistry . 5th ed., Springer, Berlin et al., 2001. 435-436.
JA Miller: “A simple sweet from an Aztec herb - hernandulcin”. Science News (January 26, 1985). here online .

[mori-1] Kenji Mori; Minoru Kato: Synthesis of (6S, 1'S) - (+) - Hernandulcin, a sweetner and its stereoisomers , Tetrahedron 42, 5895-5900, 1986.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[kima-3] Jung Hun Kima; Hyun Jin Lima; Seung Hoon Cheon: Synthesis of (+) - hernandulcin and (+) - epihernandulcin , Tetrahedron Letters 43, 4721-4722, 2002 doi : 10.1016 / S0040-4039 (02) 00939-5 .