View source for Quassin

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464378137
| Name = Quassin
| ImageFile = Quassin test ACS.png
| ImageSize = 
| ImageName = (+)-Quassin
| IUPACName = 2,12-Dimethoxypicrasa-2,12-diene-1,11,16-trione
| SystematicName = (3a''R'',3a<sup>1</sup>''S'',6a''R'',7a''S'',8''S'',11a''S'',11b''S'')-2,10-Dimethoxy-3,3a<sup>1</sup>,8,11a-tetramethyl-3a,3a<sup>1</sup>,6a,7,7a,8,11a,11b-octahydrophenanthro[10,1-''bc'']pyran-1,5,11(4''H'')-trione
| OtherNames = 
|Section1={{Chembox Identifiers
| EINECS = 200-985-9
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 59014
| InChI1 = 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
| InChIKey1 = IOSXSVZRTUWBHC-LBTVDEKVBB
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}= {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}= {{stdinchicite|correct|chemspider}}
| StdInChIKey = IOSXSVZRTUWBHC-LBTVDEKVSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 76-78-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QP1YAK6QGK
| PubChem = 65571
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 517016
| 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
| InChIKey = IOSXSVZRTUWBHC-LBTVDEKVBB
  }}
|Section2={{Chembox Properties
| C=22 | H=28 | O=6
| Appearance = White crystalline substance
| MeltingPtC = 200 to 222
| MeltingPt_notes = 
| BoilingPtC = 586
| Solubility = Insoluble
| VaporPressure = 13 mmHg  (@25 °C)
  }}
}}

'''Quassin''' is a white, bitter, crystalline substance that is the prototypical example of the family of [[quassinoid]]s. It can be extracted from the [[quassia]] tree, from which it gets its name.  It was first isolated in 1937,<ref>E.P. Clark, J. Amer. Chem. Soc. (1937)</ref> and its chemical structure was elucidated in 1961.<ref>{{cite journal |last1=Valenta |first1=Z. |last2=Papadopoulos |first2=S. |last3=Podešva |first3=C. |title=Quassin and Neoquassin |journal=Tetrahedron |date=1961 |volume=15 |issue=1–4 |pages=100–110 |doi=10.1016/0040-4020(61)80013-6}}</ref> 

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]].<ref name=ooscf-2002>Scientific Committee on Food [http://ec.europa.eu/food/fs/sc/scf/out134_en.pdf Opinion of the Scientific Committee on Food on quassin (expressed on 2 July 2002).] {{webarchive|url=https://web.archive.org/web/20110519191751/http://ec.europa.eu/food/fs/sc/scf/out134_en.pdf |date=19 May 2011 }} SCF/CS/FLAV/FLAVOUR/29 Final </ref>

Extracts of the [[Quassia amara|bitterwood tree]] (''Quassia amara'') containing quassin are used as additives in [[soft drink]]s.<ref name=ooscf-2002/>

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 ==
{{reflist}}

<!-- Metadata: see [[Wikipedia:InChI]] 
{{InChI|
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
}}
--->

[[Category:Bitter compounds]]
[[Category:Ethers]]
[[Category:Quassinoids]]
[[Category:Heterocyclic compounds with 4 rings]]
[[Category:Diketones]]
[[Category:Enones]]
[[Category:Enol ethers]]