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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28O6
Molecular Weight 388.4541
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUASSIN

SMILES

[H][C@]12C[C@@]3([H])[C@H](C)C=C(OC)C(=O)[C@]3(C)[C@@]4([H])C(=O)C(OC)=C(C)[C@]([H])(CC(=O)O1)[C@]24C

InChI

InChIKey=IOSXSVZRTUWBHC-LBTVDEKVSA-N
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

HIDE SMILES / InChI
Quassin is the archetypal example of compounds from the quassinoids family. It is a naturally occurring metabolite of the quassia tree. It was first isolated in 1937 and is known to be one of the most bitter substances used in nature. It is safe to consume and is therefore used as a food additive. Quassia extracts are used as nutritional supplements to treat anorexia, constipation, and fever. Quassin has also been used in non-medicinal/non-nutritional products such as aftershaves, furniture polish, and insect mats.

Originator

Curator's Comment: preservative agent against moths and the like

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Anti-tuberculosis activity of quassinoids.
1997 Sep
Antiviral activity of simalikalactone D, a quassinoid from Quassia africana.
2002 Jan
Patents

Sample Use Guides

No signs of acute toxicity were observed in albino rats for both oral dosing and peritoneal injections up to 100 mg/kg per day for 9 days. A statistically significant increase in intestinal movement was observed at the maximum dose.
Route of Administration: Oral
In Vitro Use Guide
Quassin was found to inhibit both the basal and LH-stimulated testosterone secretion of rat Leydig cells in a dose-dependent fashion at doses between 50 - 250 micro-g/mL.
Name Type Language
QUASSIN
INCI   MI  
INCI  
Official Name English
QUASSIN [MI]
Common Name English
QUASSIN [INCI]
Common Name English
NIGAKILACTONE D
Common Name English
2,12-DIMETHOXYPICRASA-2,12-DIENE-1,11,16-TRIONE
Common Name English
NSC-36342
Code English
Code System Code Type Description
EPA CompTox
DTXSID30878613
Created by admin on Fri Dec 15 15:25:43 GMT 2023 , Edited by admin on Fri Dec 15 15:25:43 GMT 2023
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NSC
36342
Created by admin on Fri Dec 15 15:25:43 GMT 2023 , Edited by admin on Fri Dec 15 15:25:43 GMT 2023
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PUBCHEM
65571
Created by admin on Fri Dec 15 15:25:43 GMT 2023 , Edited by admin on Fri Dec 15 15:25:43 GMT 2023
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SMS_ID
100000165914
Created by admin on Fri Dec 15 15:25:43 GMT 2023 , Edited by admin on Fri Dec 15 15:25:43 GMT 2023
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MESH
C010317
Created by admin on Fri Dec 15 15:25:43 GMT 2023 , Edited by admin on Fri Dec 15 15:25:43 GMT 2023
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EVMPD
SUB179775
Created by admin on Fri Dec 15 15:25:43 GMT 2023 , Edited by admin on Fri Dec 15 15:25:43 GMT 2023
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CAS
76-78-8
Created by admin on Fri Dec 15 15:25:43 GMT 2023 , Edited by admin on Fri Dec 15 15:25:43 GMT 2023
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ECHA (EC/EINECS)
200-985-9
Created by admin on Fri Dec 15 15:25:43 GMT 2023 , Edited by admin on Fri Dec 15 15:25:43 GMT 2023
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WIKIPEDIA
QUASSIN
Created by admin on Fri Dec 15 15:25:43 GMT 2023 , Edited by admin on Fri Dec 15 15:25:43 GMT 2023
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FDA UNII
QP1YAK6QGK
Created by admin on Fri Dec 15 15:25:43 GMT 2023 , Edited by admin on Fri Dec 15 15:25:43 GMT 2023
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MERCK INDEX
m9412
Created by admin on Fri Dec 15 15:25:43 GMT 2023 , Edited by admin on Fri Dec 15 15:25:43 GMT 2023
PRIMARY Merck Index