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12542-36-8 (Gossypol (acetic acid))

1

Identification

Gossypol (acetic acid) Gossypol (acetic acid)
Name Gossypol (acetic acid)
Formula C32H34O10
MW 578.6064
CAS No. 12542-36-8
EINECS
Smiles OC1=C(C2=C(O)C(C(C=O)=C(O)C(O)=C3C(C)C)=C3C=C2C)C(C)=CC4=C(C(C)C)C(O)=C(O)C(C=O)=C41.O=C(O)C
Synonyms (±)-Gossypol-acetic aci
InChI InChI=1S/C30H30O8.C2H4O2/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36;1-2(3)4/h7-12,33-38H,1-6H3;1H3,(H,3,4)
2

Introduction

Gossypol, a natural product isolated from cottonseeds and roots, binds to Bcl-xL protein and Bcl-2 protein with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively.

Background Information

Acetate gossypol may represent a promising new anticancer agent with a novel molecular mechanism and warrants further investigation as a single agent, or in combination with other chemotherapeutics, for human multiple myeloma with Bcl-2 overexpression. ......by BOC Sciences
Gossypol, a natural product isolated from cottonseeds and roots, binds to Bcl-xL protein and Bcl-2 protein with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively. ......by MedChemexpress Co., Ltd.
AT-101 is the orally bioavailable solvate of the R-(-) enantiomer of gossypol and acetic acid with potential antineoplastic activity. As a BH3 mimetic, R-(-)-gossypol binds to the hydrophobic surface binding groove BH3 of the anti-apoptotic proteins Bcl-2 and Bcl-xL, blocking their heterodimerization with pro-apoptotic members of the Bcl-2 family of proteins such as Bad, Bid, and Bim; this may result in the inhibition of tumor cell proliferation and the induction of tumor cell apoptosis. Racemic gossypol is a polyphenolic compound isolated from cottonseed. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus). Shelf life: >2 years if stored properly Drug formulation: ......by MedKoo Biosciences, Inc.
Gossypol-acetic acid, a polyphenolic compound isolated from cottonseeds, inhibits Bcl-2 by acting as a BH3 mimetic. ......by Target Molecule Corp.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:Light yellow to yellow Solid EBNumber:EB000012609

Storage condition

Solubility

DMSO by MedChemexpress Co., Ltd.
5

Mechanism and Indication

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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Gossypol (acetic acid) University of Michigan Comprehensive Cancer Center Larynx tumor 2012/3/31 2016/1/31 Phase 2 Clinical
Gossypol (acetic acid) University of Michigan Comprehensive Cancer Center Head and neck tumor 2010/6/30 2016/1/31 Phase 2 Clinical
Gossypol (acetic acid) Memorial Sloan-Kettering Cancer Center Metastatic non small cell lung cancer 2009/9/30 2010/5/31 Phase 2 Clinical
Gossypol (acetic acid) The Cancer Institute of New Jersey Metastatic prostate cancer 2009/7/31 2011/5/31 Phase 2 Clinical
Gossypol (acetic acid) Ascenta Therapeutics Inc Non-small-cell lung cancer 2007/9/30 2009/4/1 Phase 2 Clinical
Gossypol (acetic acid) National Cancer Institute Adrenal cortical carcinoma 2009/2/28 2012/3/1 Phase 2 Clinical
Gossypol (acetic acid) - No Development Reported
7

Safety Data of Gossypol (acetic acid)

Hazard Symbols : Xn
Risk Statements : R22;R40
Safety Statements : S22;S36
RTECS : MD7360000
WGKGermany : 3
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
Alfa Chemistry USA
BOC Sciences
CHEMSCENE, LLC 200mg/USD114();500mg/USD210() USA
Carbosynth Limited 5g/USD325()
MedChemexpress Co., Ltd. 200mg/USD114();500mg/USD210() USA
MedKoo Biosciences, Inc. USA
Santa Cruz Biotechnology, Inc. 250mg/USD120() USA
Selleck Chemicals LLC USA
Shanghai Haoyuan Chemexpress Co., Ltd. 200mg/USD114();500mg/USD210() China
Sigma-Aldrich, Inc. 250mg/USD126() USA
Target Molecule Corp. 5mg/USD24();10mg/USD45();20mg/USD88();100mg/USD198();250mg/USD329() USA
Wuhan ChemFaces Biochemical Co., Ltd. 20mg/USD100() China
Zhejiang Yixin Pharmaceutical Co., Ltd. China
10

Related Products

Other Forms of 12542-36-8

Name CAS No Formula MW
Gossypol 303-45-7 C30H30O8 518.55

Recommended Compounds in Bcl-2 Family

Name CAS No Formula MW
MIM1 509102-00-5 C17H21N3O3S 347.43
713492-66-1
Marinopyrrole A 1227962-62-0 C22H12Cl4N2O4 510.15
WEHI-539 1431866-33-9 C31H29N5O3S2 583.72
Gambogic Acid 2752-65-0 C38H44O8 628.75
ABT-199 1257044-40-8 C45H50ClN7O7S 868.44
(±)-Apogossypol 475-56-9 C28H30O6 462.5342
Gossypol 303-45-7 C30H30O8 518.55
AT-101 90141-22-3 C30H30O8 518.55
BAM7 331244-89-4 C21H19N5O2S 405.47
SZ4TA2 406231-90-1 C28H32N4O5S2 568.71
TW-37 877877-35-5 C33H35NO6S 573.7
HA14-1 65673-63-4 C17H17BrN2O5 409.23
Obatoclax 803712-79-0 C21H23N3O4S 413.49
ABT-737 852808-04-9 C42H45ClN6O5S2 813.43
Navitoclax 923564-51-6 C47H55ClF3N5O6S3 974.61
Bax inhibitor peptide V5 579492-81-2 C27H50N6O6S 586.79
A-1331852 1430844-80-6 C38H38N6O3S 658.81
A-1155463 1235034-55-5 C35H32FN5O4S2 669.79
Bz 423 216691-95-1 C27H21ClN2O2 440.92

Recommended Compounds in Same Indication

Name CAS No Formula MW
LDK378 1032900-25-6 C28H36ClN5O3S 558.14
Pemetrexed (disodium) 150399-23-8 C20H19N5Na2O6 471.37
Volasertib 755038-65-4 C34H50N8O3 618.81
ALK inhibitor 1 761436-81-1 C23H28BrN7O3S 562.48
Olaparib 763113-22-0 C24H23FN4O3 434.46
Afatinib (dimaleate) 850140-73-7 C32H33ClFN5O11 718.08
MGCD-265 analog 875337-44-3 C26H20FN5O2S2 517.5977
Crizotinib 877399-52-5 C21H22Cl2FN5O 450.34
AT-101 90141-22-3 C30H30O8 518.55
Bicalutamide 90357-06-5 C18H14F4N2O4S 430.37
Tivantinib 905854-02-6 C23H19N3O2 369.42
Enzalutamide 915087-33-1 C21H16F4N4O2S 464.44
Dovitinib 405169-16-6 C21H21FN6O 392.43
Tivozanib 475108-18-0 C22H19ClN4O5 454.86
Nordihydroguaiaretic acid 500-38-9 C18H22O4 302.36
Sunitinib 557795-19-4 C22H27FN4O2 398.47
Orteronel 566939-85-3 C18H17N3O2 307.35
Linsitinib 867160-71-2 C26H23N5O 421.49
Leuprolide (Acetate) 74381-53-6 C61H88N16O14 1269.45
TAK-700 (R-form) 752243-39-3 C18H17N3O2 307.35
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Route of Synthesis

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References

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More Information

Gossypol (acetic acid)

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