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G8761

Sigma-Aldrich

(±)-Gossypol from cotton seeds

≥95% (HPLC)

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Synonym(s):
(±)-2,2′-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
Empirical Formula (Hill Notation):
C30H30O8
CAS Number:
Molecular Weight:
518.55
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥95% (HPLC)

storage temp.

2-8°C

SMILES string

O=C([H])C1=C(C(O)=C(C2=C(C)C=C(C(C(C)C)=C(O)C(O)=C3C([H])=O)C3=C2O)C(C)=C4)C4=C(C(C)C)C(O)=C1O

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

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This Item
A1556M0253PHL89695
(±)-Gossypol from cotton seeds ≥95% (HPLC)

G8761

(±)-Gossypol from cotton seeds

L-Mimosine from Koa hoale seeds ≥98%

M0253

L-Mimosine from Koa hoale seeds

Gossypin phyproof® Reference Substance

PHL89695

Gossypin

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

Gene Information

human ... AKR1B1(231), BAD(572), BCL2(596), LDHA(3939), LDHB(3945), MCL1(4170)

Gene Information

-

Gene Information

-

Gene Information

-

General description

Gossypol is considered as an antifertility agent. It is present in cottonseed as a yellowish pigment. This reactive sesquiterpene aldehyde is present in the family Malvaceae and has a molecular mass of 518.54.

Application

(±)-Gossypol from cotton seeds has been used:
  • as a standard to quantify the gossypol content in the extracts of leaves and flower buds
  • to study its antifertility effects on spermatogenesis in NMRI mice
  • to analyse its impact on human spermatozoa
  • to incorporate into the artificial diet for larval rearing

Biochem/physiol Actions

Gossypol is a male antifertility agent and PAF antagonist/inhibitor. Gossypol is a poisonous pigment found in cottonseed and its name is derived from the botanical name of the cotton plant, Gossypium.. Gossypium is extracted from selected hybrid species between two Gossypium species, Gossypium hirsutum and Gossypium barbadens. As a PAF antagonist/inhibitor, Gossypium markedly inhibited the contractile responses of guinea pig lung parenchyma strips stimulated with leukotriene B4, seukotriene D4, and PAF-acether.

pictograms

Exclamation markHealth hazard

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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Breast cancer is the most commonly diagnosed cancer in women. Obesity is an important risk factor for developing breast cancer and is one of few risk factors that women can modify to prevent cancer. (-)-Gossypol-enriched cottonseed oil [(-)-GPCSO] contains 65%
G Sarwar Gilani et al.
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Dietary antinutritional factors have been reported to adversely affect the digestibility of protein, bioavailability of amino acids and protein quality of foods. Published data on these negative effects of major dietary antinutritional factors are summarized in this manuscript. Digestibility and
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