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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

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About This Item

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

Quality Level

100

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

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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.
Gambogic acid acts as a caspase activator and apoptosis inducer.

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

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Certificates of Analysis (COA)

Lot/Batch Number
034M4737V
121M4705V
111M4710V
088K47103
088K47102

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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
Tao Chen et al.
Molecules (Basel, Switzerland), 17(6), 6249-6268 (2012-05-29)
Gambogic acid (GA) is in a phase II clinical trial as an antitumor and antiangiogenesis agent. In this study, 36 GA derivatives were synthesized and screened in a zebrafish model to evaluate their antiangiogenic activity and toxicity. Derivatives 4, 32
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
Xu Wang et al.
Anti-cancer agents in medicinal chemistry, 12(8), 994-1000 (2012-02-22)
Gambogic acid (GA) is a caged xanthone that is derived from Garcinia hanburyi and functions as a strong apoptotic inducer in many types of cancer cells. The distinct effectiveness of GA has led to its characterization as a novel anti-cancer
Gianni Guizzunti et al.
Chembiochem : a European journal of chemical biology, 13(8), 1191-1198 (2012-04-26)
The natural product gambogic acid (GA) has shown significant potential as an anticancer agent as it is able to induce apoptosis in multiple tumor cell lines, including multidrug-resistant cell lines, as well as displaying antitumor activity in animal models. Despite
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