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G8761

Sigma-Aldrich

(±)-Gossypol from cotton seeds

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

Sinonimo/i:

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

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100 MG
274,00 €
250 MG
561,00 €

About This Item

Formula empirica (notazione di Hill):
C30H30O8
Numero CAS:
Peso molecolare:
518.55
Numero MDL:
Codice UNSPSC:
12352200
ID PubChem:
NACRES:
NA.77

274,00 €


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Nome del prodotto

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

Livello qualitativo

Saggio

≥95% (HPLC)

Temperatura di conservazione

2-8°C

Stringa SMILE

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
QBKSWRVVCFFDOT-UHFFFAOYSA-N

Descrizione generale

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.[1]

Applicazioni

(±)-Gossypol from cotton seeds has been used:
  • as a standard to quantify the gossypol content in the extracts of leaves and flower buds[2]
  • to study its antifertility effects on spermatogenesis in NMRI mice[1]
  • to analyse its impact on human spermatozoa[3]
  • to incorporate into the artificial diet for larval rearing[4]

Azioni biochim/fisiol

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.

Pittogrammi

Health hazardExclamation mark

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Acute Tox. 4 Oral - Repr. 1B

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

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


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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)
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
Daniel J Goff et al.
Cell stem cell, 12(3), 316-328 (2013-01-22)
Leukemia stem cells (LSCs) play a pivotal role in the resistance of chronic myeloid leukemia (CML) to tyrosine kinase inhibitors (TKIs) and its progression to blast crisis (BC), in part, through the alternative splicing of self-renewal and survival genes. To

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