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 Number	76-78-8^N
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL517016^Y
ChemSpider	59014^Y
ECHA InfoCard	100.000.897
EC Number	200-985-9
PubChem	65571
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 Key: IOSXSVZRTUWBHC-LBTVDEKVBB 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
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
Chemical formula	C₂₂H₂₈O₆
Molar mass	388.46 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Quassin is a white bitter, crystalline substance extracted from the quassia tree, isolated in 1937 and elucidated in 1961. It is the 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

1 2 Scientific Committee on Food Opinion of the Scientific Committee on Food on quassin (expressed on 2 July 2002). SCF/CS/FLAV/FLAVOUR/29 Final

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