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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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GAMBOGIC ACID Suppliers

InvivoChem
Tel
13549236410
Email
sales@invivochem.cn
Country
China
ProdList
6753
Advantage
58
Chengdu Peter-like Biotechnology Co., Ltd.
Tel
028-81700200 18108052721
Email
2850505130@qq.com
Country
China
ProdList
5177
Advantage
58
Huzhou ZhanShu Biotechnology Co.,Ltd
Tel
0572-8889530 18167260939
Email
zsubio@163.com
Country
China
ProdList
357
Advantage
58
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
8415
Advantage
55
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
19172
Advantage
64
Shandong Xiya Chemical Co., Ltd
Tel
4009903999 13355009207
Fax
0539-6365991
Email
3007715519@qq.com
Country
China
ProdList
18738
Advantage
57
Sichuan Kulinan Technology Co., Ltd
Tel
400-1166-196 18981987031
Fax
028-84555506 800101999
Email
cdhxsj@163.com
Country
China
ProdList
11707
Advantage
57
China Langchem Inc.
Tel
0086-21-58956006
Fax
0086-21-58956100
Country
China
ProdList
7811
Advantage
57
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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:


  • 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