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G8761

Sigma-Aldrich

(±)-Gossypol from cotton seeds

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

Synonim(y):

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

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About This Item

Wzór empiryczny (zapis Hilla):
C30H30O8
Numer CAS:
303-45-7
Masa cząsteczkowa:
518.55
Numer MDL:
MFCD00017352
Kod UNSPSC:
12352200
Identyfikator substancji w PubChem:
24895349
NACRES:
NA.77

product name

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

Poziom jakości

200

Próba

≥95% (HPLC)

temp. przechowywania

2-8°C

ciąg 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

Klucz InChI

QBKSWRVVCFFDOT-UHFFFAOYSA-N

informacje o genach

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

Opis ogólny

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.

Zastosowanie

(±)-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

Działania biochem./fizjol.

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.
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Piktogramy

Health hazardExclamation mark
GHS08,GHS07

Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

H302,H360F

Zwroty wskazujące środki ostrożności

P202 - P264 - P280 - P301 + P312 - P308 + P313 - P405

Klasyfikacja zagrożeń

Acute Tox. 4 Oral - Repr. 1B

Kod klasy składowania

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

Klasa zagrożenia wodnego (WGK)

WGK 3

Środki ochrony indywidualnej

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

Certyfikaty analizy (CoA)

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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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