QUASSIN

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 Search

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

Molecular Formula	C22H28O6
Molecular Weight	388.4541
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://ec.europa.eu/food/sites/food/files/safety/docs/fs_food-improvement-agents_flavourings-out134.pdf | https://www.webmd.com/vitamins-supplements/ingredientmono-290-quassia.aspx | www.google.ca/patents/US5747021 | https://www.google.ca/patents/US6337080 | https://www.google.ca/patents/US5747021

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

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Anti-tuberculosis activity of quassinoids.	1997 Sep	9332005

Patents

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:25:43 UTC 2023` Edited by `admin` on `Fri Dec 15 15:25:43 UTC 2023`
Record UNII	QP1YAK6QGK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUASSIN

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