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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

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

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

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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
Xiaofen Li et al.
Cell reports, 3(1), 211-222 (2012-12-25)
Gambogic acid (GA) is a natural compound derived from Chinese herbs that has been approved by the Chinese Food and Drug Administration for clinical trials in cancer patients; however, its molecular targets have not been thoroughly studied. Here, we report
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
Abhishek Shetty et al.
Plant physiology and biochemistry : PPB, 118, 643-652 (2017-08-15)
The plant derived xanthanoid gambogic acid (GA) is well known for its anticancer activity. To date, biological actions of GA on plant system have not been reported. In the present study, we evaluated the potential acute genotoxic activity of GA
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