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G8761

Sigma-Aldrich

(±)-Gossypol from cotton seeds

≥95% (HPLC), powder, PAF antagonist/inhibitor

Sinónimos:

(±)-2,2′-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)

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About This Item

Fórmula empírica (notación de Hill):
C30H30O8
Número de CAS:
303-45-7
Peso molecular:
518.55
Número MDL:
MFCD00017352
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24895349
NACRES:
NA.77

Nombre del producto

(±)-Gossypol from cotton seeds, ≥95% (HPLC)

Nivel de calidad

200

Ensayo

≥95% (HPLC)

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

QBKSWRVVCFFDOT-UHFFFAOYSA-N

Información sobre el gen

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

Descripción general

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.

Aplicación

(±)-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

Acciones bioquímicas o fisiológicas

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.

Pictogramas

Health hazardExclamation mark
GHS08,GHS07

Palabra de señalización

Danger

Frases de peligro

H302,H360F

Clasificaciones de peligro

Acute Tox. 4 Oral - Repr. 1B

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
0000423547
0000423546
0000423546
0000423547
0000380810

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Transcriptional responses underlying the hormetic and detrimental effects of the plant secondary metabolite gossypol on the generalist herbivore Helicoverpa armigera
de la Paz Celorio-Mancera M, et al.
BMC Genomics, 12(1), 575-575 (2011)
Saiyi Zhong et al.
Anticancer research, 33(3), 949-955 (2013-03-14)
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.
The British journal of nutrition, 108 Suppl 2, S315-S332 (2012-10-31)
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
Jian-Ying Guo et al.
Journal of economic entomology, 106(3), 1379-1385 (2013-07-20)
Use of plant secondary metabolic compounds is an important method for insect pest control. In this study, the survival, development, and reproduction of Bemisia tabaci (Gennadius) (Hemiptera: Aleyrodidae) MEAM1 cryptic species were compared over two consecutive generations on three cotton
Nariman Ansari et al.
Methods in cell biology, 113, 295-309 (2013-01-16)
Cell-based assays are essential in both basic research and drug discovery. Three-dimensional cellular spheroids are more realistic models of tumors and healthy tissues compared to standard two-dimensional cultures. Employing spheroids improves the reliability and the physiological significance of cell-based assays.
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