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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

Description

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

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
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.