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G8761

Sigma-Aldrich

(±)-Gossypol from cotton seeds

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

Sinônimo(s):

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

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About This Item

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

Nome do produto

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

Nível de qualidade

200

Ensaio

≥95% (HPLC)

temperatura de armazenamento

2-8°C

cadeia de caracteres 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

chave InChI

QBKSWRVVCFFDOT-UHFFFAOYSA-N

Informações sobre genes

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

Descrição geral

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.

Aplicação

(±)-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

Ações bioquímicas/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

Palavra indicadora

Danger

Frases de perigo

H302,H360F

Classificações de perigo

Acute Tox. 4 Oral - Repr. 1B

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

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

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Certificados de análise (COA)

Lot/Batch Number
069M4019V
049M4039V
12170611
028M4048V
097M4094V

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Expression of the ?glanded-plant and glandless-seed? trait of Australian diploid cottons in different genetic backgrounds
Benbouza H, et al.
Euphytica, 165(2), 211-221 (2009)
The effects of gossypol on spermatogenesis in NMRI mice
Amini, A and Kamkar F
Iranian journal of science and technology. Transaction A, Science, 29(1), 123-133 (2005)
Peter Kovacic
Current medicinal chemistry, 10(24), 2711-2718 (2003-10-08)
Gossypol, a constituent of cottonseeds, displays various drug properties, including antifertility and anticancer. Toxicity is shown against the reproductive system, heart, liver, and membranes. The compound exhibits pro- and anti-oxidant behavior. Electron transfer (ET) functionalities, present in gossypol and its
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)
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
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