(±)-Gossypol | 2579

Isolated from cotton seeds. It causes infertility in a variety of cotton pests and spermatogenesis arrest in humans. Gossypol also has antimalarial properties, preventing the growth of P. falciparum at low micromolar concentrations. It inhibits aldose reductase (Ki = 0.5 µM).Gossypol also acts as an anticancer agent, inhibiting cell growth in various cancer cell lines, in part by blocking the anti-apoptotic functions of Bcl-2 and Bcl-xL, again at low micromolar concentrations. Also acts as a non-selective competitive inhibitor of NADH binding to LDH, with K(i) values of 1.9, 1.4, and 4.2 µM for LDH-A4, -B4, and -C4, respectively.

Gossypol causes infertility in a variety of cotton pests and spermatogenesis arrest in humans. Gossypol also has antimalarial properties, preventing the growth of P. falciparum at low micromolar concentrations. It inhibits aldose reductase (Ki = 0.5 µM).Gossypol also acts as an anticancer agent, inhibiting cell growth in various cancer cell lines, in part by blocking the anti-apoptotic functions of Bcl-2 and Bcl-xL, again at low micromolar concentrations. Also acts as a non-selective competitive inhibitor of NADH binding to LDH, with K(i) values of 1.9, 1.4, and 4.2 µM for LDH-A4, -B4, and -C4, respectively

2579 | (±)-Gossypol DataSheet

Alternate Name/Synonyms: (±)-2,2′-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene; NSC 56817; NSC 524336; BL 193; Pogosin

Appearance: Yellow solid

Formulation: N/A

CAS Number: 303-45-7

Structure Available?: Y

Peptide sequence: N/A

Salt Form: No

Molecular Formula: C₃₀H₃₀O₈

Molecular Weight: 518.55

Cell-Permeable?: Yes

Purity: ≥95%

Solubilities: DMSO (>10 mg/ml) or EtOH (>10 mg/ml with slight warming)

Handling: Protect from air and light

Country of Origin: USA

Tag Line: An anticancer agent and LDH inhibitor

MDL Number: MFCD00017352

PubChem CID: 3503

SMILES: CC1=C(C(=C2C(=C1)C(=C(C(=C2C=O)O)O)C(C)C)O)C3=C(C=C4C(=C3O)C(=C(C(=C4C(C)C)O)O)C=O)C

InChi: InChI=1S/C30H30O8/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/h7-12,33-38H,1-6H3

InChi Key: QBKSWRVVCFFDOT-UHFFFAOYSA-N