Gossypol

Base Information

• Chemical Name: Gossypol
• CAS No.: 303-45-7
• Deprecated CAS: 732279-01-5,40112-23-0,123732-23-0,40112-23-0
• Molecular Formula: C30H30O8
• Molecular Weight: 518.563
• Hs Code.: 29124990
• European Community (EC) Number: 636-899-7
• NSC Number: 728875,726190,624336,56817
• UNII: 8DY2X8LXW4,XNA7DR63CQ,KAV15B369O
• DSSTox Substance ID: DTXSID5023110
• Nikkaji Number: J126.059F,J2.536.108C,J2.536.109A,J858.559H,J21.393D
• Wikipedia: Gossypol
• Wikidata: Q411882
• NCI Thesaurus Code: C529
• Pharos Ligand ID: 729J55RF7KWH
• Metabolomics Workbench ID: 28312
• ChEMBL ID: CHEMBL51483
• Mol file: 303-45-7.mol

Synonyms:Dipotassium Salt, Gossypol;Gossypol;Gossypol Dipotassium Salt;Gossypol Sodium Salt;Gossypol, (+)-Isomer;Gossypol, (+-)-Isomer;Gossypol, (-)-Isomer;Sodium Salt, Gossypol

Chemical Property of Gossypol

Chemical Property:

• Melting Point: 181-183 °C
• Refractive Index: 1.4900 (estimate)
• Boiling Point: 707.888 °C at 760 mmHg
• PKA: 7.15±0.50(Predicted)
• Flash Point: 395.872 °C
• PSA: 155.52000
• Density: 1.403 g/cm³
• LogP: 6.38220
• Storage Temp.: 2-8°C
• Solubility.: ≥25.95 mg/mL in DMSO; insoluble in H2O; ≥2.1 mg/mL in EtOH
• Water Solubility.: Soluble in 100%ethanol (25 mg/ml), DMF (25 mg/ml), acetone, DMSO (25 mM), methanol (2 mg/ml), ether, chloroform, sodium carbonat
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 518.19406791
• Heavy Atom Count: 38
• Complexity: 780

Purity/Quality:

Gossypol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xn,Xi
• Statements: 22-40-36/37/38
• Safety Statements: 22-36-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC2=C(C(=C(C(=C2C(C)C)O)O)C=O)C(=C1C3=C(C4=C(C=C3C)C(=C(C(=C4C=O)O)O)C(C)C)O)O
• Recent ClinicalTrials: Safety, Tolerability, and Efficacy of AT101 in Patients With Relapsed or Refractory B-cell Non-Hodgkin's Lymphoma
• Description: Gossypol is mainly present in the roots, stems, leaves, and seeds of the plant cotton, and the highest content is found in cotton seeds. Its chemical structure was first determined by Adams in 1938 and was used to be studied in antitumor research.
• Physical properties: Appearance: plate or needle-like crystals with yellow color, odorless, and tasteless. Solubility: do not dissolve in water, slightly soluble in ethanol, and soluble in chloroform, ether, acetone, ethyl acetate, dichloroethane, carbon tetrachloride, and pyridine. Difficult to dissolve in cyclohexane, benzene, and petroleum ether. Melting point: 184–214?°C. Gossypol has a chiral structure with two optical isomers in the left and right. The formic acid gossypol or gossypol acetate was commonly used.
• Uses: antispermatogenic, antineoplastic, antiHIV Gossypol acts as an inhibitor for several dehydrogenase enzymes. Gossypol has also long been known to possess antimalarial properties. Gossypol provided reliable contraception. gossypol provokes infertility and causes spermatogenesis. Gossypol is used as an active antifertility agent in a variety of male animals, including mice, rats, hamsters, monkeys, rabbits, and bulls.
• Indications: This product as gossypol acetate is recorded in the tenth volume of national standards for chemical drugs. Solid formulations include compound acetate gossypol tablets and gossypol potassium chloride vitamin B capsule. Gossypol was used as male contraceptive drug in clinic previously but terminated due to the induced severer hypokalemia. Now, compound acetate gossypol tablets consisted of acetate gossypol and potassium chloride, vitamins are used for the treatment of uterine functional bleeding, uterine fibroids, and menorrhagia and endometriosis.
• Clinical Use: Due to the presence of hypokalemia and irreversible antifertility risk of gossypol, the clinical indications of male contraceptives are not approved by the Chinese Food and Drug Administration. At present, gossypol and its derivatives are mainly used for female uterine fibroids, functional uterine bleeding, and endometriosis treatment. In addition, the treatment of gossypol and its derivatives in the tumor is gradually confirmed clinically, such as gossypol combined with docetaxel or cisplatin for the treatment of malignant non-small cell lung cancer, and is currently in phase III clinical trial . Gossypol combined with rituximab can achieve better therapeutic efficacy against granulocytic leukemia and is currently in phase II clinical trials .

Technology Process of Gossypol

There total 43 articles about Gossypol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

(±)-gossypol acetic acid (5453-04-3,866541-93-7,1189561-66-7) → (rac)-gossypol (303-45-7)

Guidance literature:

With iron(III) chloride; In acetone; at 60 ℃;

Reference yield: 76.1%

2,3,8-trihydroxy-4-isopropyl-6-methyl-1-naphthaldehyde (40817-07-0) → (rac)-gossypol (303-45-7)

Guidance literature:

With tert-butyl peroxyacetate; In 1,2-dichloro-ethane; at 80 ℃; for 4h; Inert atmosphere;

DOI:10.1002/ejoc.201301126

Reference yield: 72.0%

apogossypol (784206-41-3,475-56-9) + N,N'-diphenylformamidine (864131-95-3) → (rac)-gossypol (303-45-7)

Guidance literature:

With hydroquinone; at 180 ℃; for 2.5h; under 5 - 15 Torr;

DOI:10.1021/jo00217a021

upstream raw materials:

4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one)

Gossypol

apogossypol

N,N'-diphenylformamidine

Downstream raw materials:

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-(4-nitro-benzylimine)

apogossypol

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-(4-carboxy-phenylimine)

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-phenethylimine

Refernces

• 1、 Liu, Jinggao,Stipanovic, Robert D.,Bell, Alois A.,Puckhaber, Lorraine S.,Magill, Clint W.. "Stereoselective coupling of hemigossypol to form (+)-gossypol in moco cotton is mediated by a dirigent protein". . p. 3038 - 3042. Retrieved 2008.
• 2、 Cao, Tongxiang,Kong, Yi,Luo, Kui,Chen, Lianfen,Zhu, Shifa. "Cascade Claisen Rearrangement: Rapid Synthesis of Polysubstituted Salicylaldehydes and Total Syntheses of Hemigossypol and Gossypol". . p. 8702 - 8707. Retrieved 2018.
• 3、 Jiang, Hai-Xia,Cao, Xing-Xin,Huang, Hao,Jiang, Biao. "An expedient route for the practical preparation of optically active (-)-gossypol". . p. 2437 - 2441. Retrieved 2007.
• 4、 -. "Synthetic method of semi-gossypol, gossypol and analogues of semi-gossypol and gossypol". Paragraph 0141-0143; 0159; 0235-0238. . Retrieved 2019/08/30.