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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
082H4021
082H4022

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L Blackstaffe et al.
Melanoma research, 7(5), 364-372 (1998-01-16)
The cytotoxicity of the (-)- and (+)-isomers and the quinone metabolite gossypolone prepared from the naturally occurring polyphenolic dialdehyde gossypol were compared using two human melanoma cell lines (SK-mel-19 and SK-mel-28) with a similar growth rate, one melanotic (melanin content
Y Gu et al.
The Journal of steroid biochemistry and molecular biology, 38(6), 709-715 (1991-06-01)
Gossypolone, a proposed major metabolite of gossypol, was synthesized and investigated for its effect on progesterone synthesis in cultured bovine luteal cells. Gossypolone inhibited human chorionic gonadotropin(hCG)-stimulated progesterone secretion, reduced substrate-enhanced conversions of 25-hydroxycholesterol to pregnenolone and of pregnenolone to
H Ohmura
Nihon Ika Daigaku zasshi, 63(3), 181-189 (1996-06-01)
Gossypol (GP), a male antifertility agent, and Gossypolone (GN), a major metabolite of GP, have been shown to have a suppressive effect on steroidogenesis in bovine luteal cells. We examined the effect of GP, GN and serum obtained from rats
V T Dao et al.
European journal of medicinal chemistry, 35(9), 805-813 (2000-09-28)
Gossypol, gossypolone, reduced gossypol and new Schiff's bases of racemic gossypol and gossypolone were extracted or synthesized. Their cytotoxic activities on KB human cancer cells were determined. Gossypolone and the ethylamine derivative of gossypolone were the most active compounds (IC(50)
Jay E Mellon et al.
Journal of agricultural and food chemistry, 60(10), 2740-2745 (2012-02-14)
Racemic gossypol and its related derivatives gossypolone and apogossypolone demonstrated significant growth inhibition against a diverse collection of filamentous fungi that included Aspergillus flavus, Aspergillus parasiticus, Aspergillus alliaceus, Aspergillus fumigatus, Fusarium graminearum, Fusarium moniliforme, Penicillium chrysogenum, Penicillium corylophilum, and Stachybotrys
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