GAMBOGIC ACID

ChemicalBook > CAS DataBase List > GAMBOGIC ACID

Product Name: GAMBOGIC ACID
CAS No.: 2752-65-0
Chemical Name: GAMBOGIC ACID
Synonyms: Gambogic Acid (Guttatic Acid, Guttic Acid);GUTTIC ACID;GaMbogic aci;cambogicacid;β-Guttiferin;gamogic acid;GUTTATIC ACID;GAMBOGIC ACID;β-Guttilactone;b’’-guttiferin
CBNumber: CB1281965
Molecular Formula: C38H44O8
Formula Weight: 628.75
MOL File: 2752-65-0.mol

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GAMBOGIC ACID Property

Melting point:: 88.5°C
Boiling point:: 586.06°C (rough estimate)
alpha: D20 -685° (methanol)
Density: 1.1057 (rough estimate)
refractive index: 1.5290 (estimate)
storage temp.: -20°C
solubility: DMSO: ≥10mg/mL
form: powder
pka: 4.58±0.36(Predicted)
color: yellow to orange
Stability:: Stable for 1 year as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChIKey: GEZHEQNLKAOMCA-XKZIYDEJSA-N
LogP: 6.490 (est)

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Safety

Hazard Codes: T
Risk Statements: 25-36/37/38
Safety Statements: 26-45
RIDADR: UN 2811 6.1 / PGIII
WGK Germany: 1
RTECS: PB9268200
HS Code: 29189900
Toxicity: LD50 unreported in mammal (species unspecified): 55mg/kg

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PHL80455
Product name: Gambogic acid
Purity: phyproof Reference Substance
Packaging: 10mg
Price: $375
Updated: 2024/03/01

Sigma-Aldrich

Product number: 345701
Product name: Gambogic acid
Packaging: 25mg
Price: $265
Updated: 2024/03/01

Cayman Chemical

Product number: 14761
Product name: Gambogic Acid
Purity: ≥95% (mixture of epimers)
Packaging: 1mg
Price: $33
Updated: 2024/03/01

Cayman Chemical

Product number: 14761
Product name: Gambogic Acid
Purity: ≥95% (mixture of epimers)
Packaging: 5mg
Price: $89
Updated: 2024/03/01

Cayman Chemical

Product number: 14761
Product name: Gambogic Acid
Purity: ≥95% (mixture of epimers)
Packaging: 10mg
Price: $126
Updated: 2024/03/01

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GAMBOGIC ACID Chemical Properties,Usage,Production

Description

Gambogic acid (2752-65-0) induces apoptosis in a variety of cell lines acting as an antagonist of Bcl-2 family proteins (IC50 < 1 mM)1, however additional targets may contribute to its cytotoxicity. It suppresses cancer invasion and migration by inhibiting TGFb1-induced epithelial-to-mesenchymal transition.2 Potentiates the chemosensitivity of cancer cells to other agents.3 Down-regulates surviving, reversing docetaxel resistance in cancer cells.4

Uses

antiinflammatory, cytotoxic, inhibits HeLa cells in vitro;

Definition

ChEBI: A natural product found in Garcinia hanburyi.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biological Activity

Natural product isolated from the Garcinia hanburyi tree. Induces apoptosis in several tumor cell lines including T47D cells. Activates caspases with an EC 50 value of 0.78-1.64 μ M and competitively inhibits antiapoptotic Bcl-2 family proteins (IC 50 values are 1.47, 1.21, 2.02, 0.66, 1.06 and 0.79 μ M for Bcl-XL, Bcl-2, Bcl-W, Bcl-B, Bfl-1 and Mcl-1 respectively). Also blocks K IR 2.1 channels (EC 50 ≤ 100 nM).

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.

Anticancer Research

Gambogic acid is a xanthonoid, also known as kokum that is a resin from Garciniaindica, that can inhibit the proliferation of human breast, hepatoma, lung, and gastriccarcinoma cells. It is also an apoptotic inducer and inhibits telomerase and theexpression of telomerase reverse transcriptase mRNA and its promoter. It also suppressesCDK7-mediated CDC2/p34 phosphorylation, downregulates Bcl-2, andinteracts with c-myc. By interacting with transferrin receptors, it mediates apoptosisof cancer cells. It inhibits NF-κB pathway. In vivo and in vitro experiments determinedits potential to inhibit angiogenesis and VGEF-2 receptor, and thus it inhibitshuman endothelial cell growth, invasion, and migration, microvessel growth, andtube formation (Zhang et al. 2004; Pandey et al. 2007; Aggarwal et al. 2008).
GA, extract from Garcinia hanburyi, the most important active constituent of gamboge,inhibits the heat shock protein (Hsp90) (Zhang 2010). Hsp90 is the majorprotein in tumour regeneration as well as cell signalling, and its inhibition results ininduction of ER stress, thereby activating UPR target genes and ER stress sensorswhich further cause cell death (Lamoureux et al. 2014). Severe or sustained ERstress increases CHOP expression and stimulates IRE1α apoptotic signalling, ATF6and PERK. CHOP being the major regulator of Bcl2, Bim and DR5 leads to cellularapoptosis preventing tumour progression (Krajarng et al. 2015).

References

1) Zhai et al. (2008), Gambogic acid is an antagonist of antiapoptotic Bcl-2 family proteins; Mol. Cancer Ther. 7 1639 2) Zhao et al. (2017), Gambogic acid suppresses cancer invasion and migration by inhibiting TGFβ1-induced epithelial-to-mesenchymal transition; Oncotarget 8 27120 3) Wei et al. (2017), Gambogic acid potentiates the chemosensitivity of colorectal cancer cells to 5-fluorouracil by inhibiting proliferation and inducing apoptosis; Exp. Ther. Med. 13 662 4) Wang et al. (2008), Gambogic acid, a potent inhibitor of surviving, reverses docetaxel resistance in gastric cancer cells; Cancer Lett. 262 214

GAMBOGIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from GAMBOGIC ACID manufacturers

Shanghai Standard Technology Co., Ltd.

Product: Gambogic acid 2752-65-0
Price: US $0.00/mg
Min. Order: 5mg
Purity: ≥98%(HPLC)
Supply Ability: 10 g
Release date: 2019-12-27

Career Henan Chemical Co

Product: GAMBOGIC ACID 2752-65-0
Price: US $1.00/kg
Min. Order: 1g
Purity: 99%
Supply Ability: 100KG
Release date: 2018-12-24

2752-65-0, GAMBOGIC ACIDRelated Search:

4'-Hydroxynonanophenone 4-Hexanoylresorcinol 6-METHYL-4-CHROMANONE GAMBOGIC ACID 2-ETHOXYCYCLOHEXANONE 3,7-DIMETHYL-2-METHYLENE-OCT-6-ENAL 2,2,5,5-TETRAMETHYLTETRAHYDROFURAN 2,2-DIMETHYL-CHROMAN-4-ONE 2-ETHYL-2-METHYL-CHROMAN-4-ONE CHEMBRDG-BB 6484841 5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE 5,7-dihydroxy-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one CHEMBRDG-BB 6571093 CHEMBRDG-BB 4021965 3-(3,5-DIMETHYL-4-METHOXYPHENYL)-2-METHYL-1-PROPENE 7-METHOXY-2,2-DIMETHYL-3-CHROMENE DIHYDROSORBICILLIN 7-HYDROXY-2,2-DIMETHYL-CHROMAN-4-ONE

GaMbogic aci

BETA-GUTTIFERIN

BETA-GUTTILACTONE

GAMBOGIC ACID

GUTTATIC ACID

β-Guttilactone

Gambogic acid, 95%, a caspases activator

2-Butenoic acid, 2-methyl-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-hydroxy-3,3,11-trimethyl-13-(3-methyl-2-buten-1-yl)-11-(4-methyl-3-penten-1-yl)-7,15-dioxo-1,5-methano-1H,3H,11H-furo[3,4-g]pyrano[3,2-b]xanthen-1-yl]-, (2Z)-

1,5-Methano-1H,3H,11H-furo(3,4-g)pyrano(3,2-b)xanthene-1-crotonic acid

Gambogic acid, >=98%

GUTTIC ACID

(z)-methyl-3-pentenyl)-

1,5-methano-1h,3h,11h-furo(3,4-g)pyrano(3,2-b)xanthene-1-crotonicacid,3a,4,5,

3,3,11-tetramethyl-13-(3-methyl-2-butenyl)-11-(4-7-tetrahydro-8-hydroxy-alph

b’’-guttiferin

cambogicacid

1,51,5-Methano-1H,3H,11H-furo(3,4-G)pyrano(3,2-B)xanthene-1-crotonic acid

B"-Guttiferrin

Beta-Guttiferrin

Guttatic acid Guttic acid

(2Z)-2-Methyl-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-hydroxy-3,3,11-trimethyl-13-(3-methyl-2-butenyl)-11-(4-methyl-3-pentenyl)-7,15-dioxo-1,5-methano-1H,3H,11H-furo[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-butenoicacid

alpha-GaMbogic acid

β-Guttiferin

Gambogic acid, 97%(HPLC)

R,S-Gambogic acid

Gambogic Acid, Garcinia hanburyi - CAS 2752-65-0 - Calbiochem

Gambogic Acid (Guttatic Acid, Guttic Acid)

gamogic acid

(Z)-4-((1S,3aR,5S,11R,14aS)-8-Hydroxy-2,2,11-trimethyl-13-(3-methylbut-2-en-1-yl)-11-(4-methylpent-3-en-1-yl)-4,7-dioxo-1,2,5,7-tetrahydro-11H-1,5-methanofuro[3,2-g]pyrano[3,2-b]xanthen-3a(4H)-yl)-2-methylbut-2-enoic acid

2-Butenoic acid,2-methyl-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-hydroxy-3,3,11-trimethyl-13-(3-methyl-2-buten-1-yl)-11-(4-methyl-3-penten-1-yl)-7,15-dioxo-1,5-methano-1H,3H,11H-furo[3,4-g]pyran

Gambogic acid (7CI)

(Z)-4-((1S,3aR,11R,14aS)-8-hydroxy-2,2,11-trimethyl-13-(3-methylbut-2-en-1-yl)-11-(4-methylpent-3-en-1-yl)-4,7-dioxo-2,3a,4,5,7,11-hexahydro-1H-1,5-methanofuro[3,2-g]pyrano[3,2-b]xanthen-3a-yl)-2-methylbut-2-enoic acid

2752-65-0

C38H44O8

Inhibitors

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract