Quassin

Quassin

IUPAC name 2,12-dimethoxypicrasa-2,12-diene-1,11,16-trione
Other names (3aS,6aR,7aS,8S,11aS,11bS,11cS) -1,3a,4,5,6a,7,7a,8,11,11a,11b,11c-dodecahydro-2,10-dimethoxy-3,8,11a,11c- tetramethyldibenzo[de,g]chromene-1,5,11-trione
Identifiers
CAS number	76-78-8^N
PubChem	65571
ChemSpider	59014^Y
EC number	200-985-9
ChEMBL	CHEMBL517016^Y
Jmol-3D images	Image 1
SMILES O=C1C(\OC)=C/[C@@H](C)[C@H]4[C@]1([C@H]3C(=O)C(\OC)=C(/[C@@H]2CC(=O)O[C@@H]([C@@]23C)C4)C)C
InChI InChI=1S/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3/t10-,12+,13+,15-,19+,21-,22+/m1/s1^Y= ^Y Key: IOSXSVZRTUWBHC-LBTVDEKVSA-N^Y= ^Y InChI=1/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3/t10-,12+,13+,15-,19+,21-,22+/m1/s1 Key: IOSXSVZRTUWBHC-LBTVDEKVBB
Properties
Molecular formula	C₂₂H₂₈O₆
Molar mass	388.45 g mol⁻¹
Appearance	White crystalline substance
Melting point	200-222 °C
Boiling point	586 °C
Solubility in water	Insoluble
Vapor pressure	13 mmHg (@25 °C)
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Quassin is a white bitter, crystalline substance extracted from the quassia tree. It is one of the most bitter substances found in nature with a bitter threshold of 0.08 ppm and it is 50 times more bitter than quinine.^[1]

Quassin is used as a medicine in traditional Chinese medicine.

Extracts of the Bitter tree (or bitter wood) (Quassia amara L. or Picrasma excelsa) are also used as additives in soft drinks.^[1]

Although its skeleton possesses 20 carbon atoms, quassin is not a diterpene but rather a triterpene lactone, which derives from euphol by loss of 10 carbon atoms including C4.

References

^ ^a ^b Scientific Committee on Food Opinion of the Scientific Committee on Food on quassin (expressed on 2 July 2002). SCF/CS/FLAV/FLAVOUR/29 Final