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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
Molecular Weight:
628.75
MDL Number:
MFCD16878985
MOL File:
2752-65-0.mol
Last updated:2023-06-08 09:02:14

GAMBOGIC ACID Properties

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)
FDA UNII 8N585K83U2

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301-H315-H319-H335
Precautionary statements  P261-P264-P270-P301+P310-P302+P352-P305+P351+P338
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
NFPA 704
0
2 0

GAMBOGIC ACID price More Price(39)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHL80455 Gambogic acid phyproof Reference Substance 2752-65-0 10mg $375 2024-03-01 Buy
Sigma-Aldrich 345701 Gambogic acid 2752-65-0 25mg $265 2024-03-01 Buy
Cayman Chemical 14761 Gambogic Acid ≥95% (mixture of epimers) 2752-65-0 1mg $33 2024-03-01 Buy
Cayman Chemical 14761 Gambogic Acid ≥95% (mixture of epimers) 2752-65-0 5mg $89 2024-03-01 Buy
Cayman Chemical 14761 Gambogic Acid ≥95% (mixture of epimers) 2752-65-0 10mg $126 2024-03-01 Buy
Product number Packaging Price Buy
PHL80455 10mg $375 Buy
345701 25mg $265 Buy
14761 1mg $33 Buy
14761 5mg $89 Buy
14761 10mg $126 Buy

GAMBOGIC ACID Chemical Properties,Uses,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

Global( 224)Suppliers
Supplier Tel Email Country ProdList Advantage
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070 product@chemlin.com.cn CHINA 3012 60
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3620 58
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
Chengdu Biopurify Phytochemicals Ltd.
+8618080483897 sales@biopurify.com China 3424 58
Hubei xin bonus chemical co. LTD
86-13657291602 linda@hubeijusheng.com CHINA 22968 58
BOC Sciences
+1-631-485-4226 inquiry@bocsci.com United States 19553 58
Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58
Shanghai Standard Technology Co., Ltd.
18502101150 ft-sales@nature-standard.com CHINA 1923 58
Neostar United (Changzhou) Industrial Co., Ltd.
+86-519-519-85557386 marketing1@neostarunited.com China 8348 58
Wuhan ChemNorm Biotech Co.,Ltd.
+86-27-8439 4403 18971486879 sales@chemnorm.com CHINA 2935 58

View Lastest Price from GAMBOGIC ACID manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Gambogic acid pictures 2023-02-24 Gambogic acid
2752-65-0
US $0.00 / mg 5mg ≥98%(HPLC) 10 g Shanghai Standard Technology Co., Ltd.
cambogicacid pictures 2023-02-13 cambogicacid
2752-65-0
US $90.00 / KG 1KG 99% 100mt Hebei baicao biology science and technology co., ltd
GAMBOGIC ACID pictures 2019-07-06 GAMBOGIC ACID
2752-65-0
US $1.00 / kg 1g 99% 100KG Career Henan Chemical Co
  • Gambogic acid pictures
  • Gambogic acid
    2752-65-0
  • US $0.00 / mg
  • ≥98%(HPLC)
  • Shanghai Standard Technology Co., Ltd.
  • cambogicacid pictures
  • cambogicacid
    2752-65-0
  • US $90.00 / KG
  • 99%
  • Hebei baicao biology science and technology co., ltd

GAMBOGIC ACID Spectrum

GaMbogic aci BETA-GUTTIFERIN BETA-GUTTILACTONE GAMBOGIC ACID GUTTATIC ACID β-Guttilactone 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, 95%, a caspases activator 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