Quassin

Quassin

Names
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 Registry Number	76-78-8 N
ChEMBL	ChEMBL517016 Y
ChemSpider	59014 Y
EC number	200-985-9
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
Jmol-3D images	Image
PubChem	65571
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
Properties
Molecular formula	C22H28O6
Molar mass	388.45 g·mol−1
Appearance	White crystalline substance
Melting point	200 to 222 °C (392 to 432 °F; 473 to 495 K)
Boiling point	586 °C (1,087 °F; 859 K)
Solubility in water	Insoluble
Vapor pressure	13 mmHg (@25 °C)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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