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G4528

Sigma-Aldrich

Gossypolone

~98%

Synonym(s):

6,6′,7,7′-Tetrahydroxy-5,5′-diisopropyl-3,3′-dimethyl-(2,2′-binaphthalene)-1,1′,4,4′-tetraone-8,8′-dicarboxyaldehyde

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About This Item

Empirical Formula (Hill Notation):
C30H26O10
CAS Number:
4547-72-2
Molecular Weight:
546.52
MDL number:
MFCD00133381
UNSPSC Code:
41116105
PubChem Substance ID:
329799929

assay

~98%

storage temp.

2-8°C

SMILES string

CC(C)c1c(O)c(O)c(C=O)c2C(=O)C(=C(C)C(=O)c12)C3=C(C)C(=O)c4c(C(C)C)c(O)c(O)c(C=O)c4C3=O

InChI

1S/C30H26O10/c1-9(2)15-21-19(13(7-31)25(35)29(15)39)27(37)17(11(5)23(21)33)18-12(6)24(34)22-16(10(3)4)30(40)26(36)14(8-32)20(22)28(18)38/h7-10,35-36,39-40H,1-6H3

InChI key

YSPBCFMMSKAENM-UHFFFAOYSA-N

Biochem/physiol Actions

Antimotile agent on human spermatozoa;[1] suppressor of progesterone synthesis on bovine luteal cells.[2]

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
082H4022
082H4021

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I C Kim et al.
Contraception, 30(3), 253-259 (1984-09-01)
The comparative in vitro spermicidal effects of (+)-gossypol, (-)-gossypol and (+/-)-gossypol were evaluated on the spermatozoa of human, monkey, rabbit, mouse, rat and hamster. The spermicidal effects of gossypol isomers were also compared with those of gossypolone, which is a
Vi-Thuy Dao et al.
Bioorganic & medicinal chemistry, 11(9), 2001-2006 (2003-04-03)
New dithiane or dithiolane derivatives of gossypol and gossypolone were synthesized with dithiolethane or dithiolpropane in the presence of BF(3)/Et(2)O. These thioderivatives exhibited low toxicity on KB cells (human epidermoid carcinoma cells of the mouth). They react easily with electrophiles
Y Gu et al.
Research communications in chemical pathology and pharmacology, 72(1), 27-38 (1991-04-01)
We have reported that gossypol, an antifertility agent, and gossypolone, a major metabolite of gossypol, inhibited steroidogenesis in bovine luteal cells in vitro. In the current study, the effects of these two compounds on steroidogenesis were examined in adrenocortical cells
M D Shelley et al.
Cancer letters, 135(2), 171-180 (1999-03-30)
The naturally occurring compound, gossypol, has been previously used as a male oral contraceptive, for the treatment of benign gynaecological conditions and cancer patients. Long-term daily dosing with gossypol is associated with minimal side effects and no myelosuppression. Since gossypol
X S Liang et al.
Investigational new drugs, 13(3), 181-186 (1995-01-01)
Preclinical and clinical studies have pointed to the antitumor potential of the naturally occurring polyphenolic binaphthyl dialdehyde, gossypol, as well as its purified (-,+) enantiomers. To explore further the antitumor properties of this multifunctional agent, we synthesized several reactive derivatives
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