Quassin

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Quassin
Quassin test ACS.png
Names
IUPAC name
2,12-Dimethoxypicrasa-2,12-diene-1,11,16-trione
Systematic IUPAC name
(3aR,3a1S,6aR,7aS,8S,11aS,11bS)-2,10-Dimethoxy-3,3a1,8,11a-tetramethyl-3a,3a1,6a,7,7a,8,11a,11b-octahydrophenanthro[10,1-bc]pyran-1,5,11(4H)-trione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.897 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-985-9
PubChem CID
UNII
  • 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 Yes check.svgY=  Yes check.svgY
    Key: IOSXSVZRTUWBHC-LBTVDEKVSA-N Yes check.svgY=  Yes check.svgY
  • 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
  • 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
C22H28O6
Molar mass 388.460 g·mol−1
AppearanceWhite 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)
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).
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Quassin is a white, bitter, crystalline substance that is the prototypical example of the family of quassinoids. It can be extracted from the quassia tree, from which it gets its name. It was first isolated in 1937, [1] and its chemical structure was elucidated in 1961. [2]

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. [3]

Extracts of the bitterwood tree (Quassia amara) containing quassin are used as additives in soft drinks. [3]

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.

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<i>Quassia</i> Genus of plants in the Simaroubaceae family found in the tropics of the world

Quassia is a plant genus in the family Simaroubaceae. Its size is disputed; some botanists treat it as consisting of only one species, Quassia amara from tropical South America, while others treat it in a wide circumscription as a pantropical genus containing up to 40 species of trees and shrubs.

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Saponins, also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed but found particularly in soapwort, a flowering plant, the soapbark tree, common corn-cockle, baby’s breath and soybeans. They are used in soaps, medicines, fire extinguishers, as dietary supplements, for synthesis of steroids, and in carbonated beverages. Saponins are both water and fat soluble, which gives them their useful soap properties. Some examples of these chemicals are glycyrrhizin and quillaia, a bark extract used in beverages.

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<span class="mw-page-title-main">Lactisole</span> Chemical compound

Lactisole is the sodium salt and commonly supplied form of 2-(4-methoxyphenoxy)propionic acid, a natural carboxylic acid found in roasted coffee beans. Like gymnemic acid, it has the property of masking sweet flavors and is used for this purpose in the food industry.

<i>Quassia amara</i> Species of tree

Quassia amara, also known as amargo, bitter-ash, bitter-wood, or hombre grande is a species in the genus Quassia, with some botanists treating it as the sole species in the genus. The genus was named by Carl Linnaeus who named it after the first botanist to describe it: the Surinamese freedman Graman Quassi. Q. amara is used as insecticide, in traditional medicine and as additive in the food industry.

<i>Picrasma quassioides</i> Species of tree

Picrasma quassioides is a species of Picrasma native to temperate regions of southern Asia, from the northeast of Pakistan east along the Himalaya and through East Asia from southern, central and eastern China to Taiwan, Japan and Korea.

<i>Simarouba glauca</i> Species of tree

Simarouba glauca is a flowering tree that is native to Florida, South America, and the Caribbean. Common names include paradise-tree, dysentery-bark, and bitterwood. The tree is well suited for warm, humid, tropical regions. Its cultivation depends on rainfall distribution, water holding capacity of the soil, and sub-soil moisture. It is suited for temperature range of 10 to 40 °C, and can grow at elevations from sea level to 1,000 m (3,300 ft). It grows 40 to 50 ft tall and has a span of 25 to 30 ft. It bears yellow flowers and purple elongated oval fleshy fruits.

The Unique Ingredient Identifier (UNII) is an alphanumeric identifier linked to a substance's molecular structure or descriptive information and is generated by the Global Substance Registration System (GSRS) of the Food and Drug Administration (FDA). It classifies substances as chemical, protein, nucleic acid, polymer, structurally diverse, or mixture according to the standards outlined by the International Organization for Standardization in ISO 11238 and ISO DTS 19844. UNIIs are non-proprietary, unique, unambiguous, and free to generate and use. A UNII can be generated for substances at any level of complexity, being broad enough to include "any substance, from an atom to an organism."

<span class="mw-page-title-main">Ethane-1,1-dithiol</span> Chemical compound

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<span class="mw-page-title-main">Quassinoid</span> Class of chemical compounds

Quassinoids are degraded triterpene lactones of the Simaroubaceae plant family grouped into C-18, C-19, C-20, C-22 and C-25 types. The prototypical member of the group, quassin, was first described in the 19th century from plants of the genus Quassia from which it gets its name. It was isolated in 1937, and its structure elucidated in 1961.

<i>N</i>,<i>N</i>-Dimethylphenethylamine Chemical compound

N,N-Dimethylphenethylamine (N,N-DMPEA) is a substituted phenethylamine that is used as a flavoring agent. It is an alkaloid that was first isolated from the orchid Eria jarensis. Its aroma is described as "sweet, fishy". It is mainly used in cereal, cheese, dairy products, fish, fruit and meat. It is also being used in pre-workout and bodybuilding supplements with claims of a stimulant effect.

<i>Samadera indica</i> Species of plant

Samadera indica, the bitter wood or Niepa bark tree, is a species of plant in the family Simaroubaceae. It is a shrub or tree and grows primarily in wet tropical regions, from west Africa, through India, then down through Indonesia to Malesia.

References

  1. E.P. Clark, J. Amer. Chem. Soc. (1937)
  2. Valenta, Z.; Papadopoulos, S.; Podešva, C. (1961). "Quassin and Neoquassin". Tetrahedron. 15 (1–4): 100–110. doi:10.1016/0040-4020(61)80013-6.
  3. 1 2 Scientific Committee on Food Opinion of the Scientific Committee on Food on quassin (expressed on 2 July 2002). Archived 19 May 2011 at the Wayback Machine SCF/CS/FLAV/FLAVOUR/29 Final