Skip to Content
Merck
All Photos(1)

Documents

G8171

Sigma-Aldrich

Gambogic acid

≥95% (HPLC), powder

Synonym(s):

1,5-Methano-1H,3H,11H-furo(3,4-g)pyrano(3,2-b)xanthene-1-crotonic acid, B"-Guttiferrin, Beta-Guttiferrin, Beta-Guttilactone, Cambogic acid, Guttatic acid, Guttic acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C38H44O8
CAS Number:
2752-65-0
Molecular Weight:
628.75
UNSPSC Code:
12352200
PubChem Substance ID:
329799975

Assay

≥95% (HPLC)

form

powder

color

yellow to orange

solubility

DMSO: ≥10 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

C\C(C)=C\CC[C@@]1(C)Oc2c(C\C=C(\C)C)c3O[C@@]45[C@@H]6C[C@@H](C=C4C(=O)c3c(O)c2C=C1)C(=O)[C@]5(C\C=C(\C)C(O)=O)OC6(C)C

InChI

1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-/t23-,27+,36-,37+,38-/m1/s1

InChI key

GEZHEQNLKAOMCA-RRZNCOCZSA-N

Looking for similar products? Visit Product Comparison Guide

Biochem/physiol Actions

Gambogic acid acts as a caspase activator and apoptosis inducer, which causes an irreversible arrest in the G2/M phase of the cell cycle.

Features and Benefits

This compound is featured on the Caspases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Jing Geng et al.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], 62(2), 165-172 (2012-10-16)
Gambogic acid (GBA) targeted Heat shock protein 90 (Hsp90) and prohibited TNF-α/NF-κB signaling pathway. It can be inferred that the anti-inflammatory activity of GBA results from inhibiting the cytokine production via NF-κB signaling pathway. We used the RAW264.7 cell line
Jing Yang et al.
Journal of natural products, 75(6), 1108-1116 (2012-06-06)
Gambogic acid (1) is a cytotoxic caged xanthone derived from the resin of Garcinia hanburyi. Compound 1 selectively induces apoptosis in cancer cells, at least partially, by targeting the stress response to reactive oxygen species (ROS). However, the molecular mechanism
Hao-Peng Sun et al.
Chemistry & biodiversity, 9(8), 1579-1590 (2012-08-18)
The natural product gambogic acid exhibits high potency in inhibiting cancer cell lines. Rational medicinal modifications on gambogic acid will improve its physicochemical properties and drug-like characters. To investigate the structure-activity relationship of gambogic acid and also to find rational
Li-jing Yang et al.
Acta pharmacologica Sinica, 34(2), 191-198 (2013-01-01)
Gambogic acid (GA) is the main active ingredient of gamboge, a brownish to orange dry resin secreted from Garcinia hanburyi, a plant that is widely distributed in nature. Recent in vitro and in vivo studies have demonstrated that GA exerts
Lianghua Fang et al.
International journal of nanomedicine, 7, 4109-4118 (2012-08-14)
The present study evaluated whether magnetic nanoparticles containing Fe(3)O(4) could enhance the activity of gambogic acid in human colon cancer cells, and explored the potential mechanisms involved. Cytotoxicity was evaluated by MTT assay. The percentage of cells undergoing apoptosis was
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service