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SML0724

Sigma-Aldrich

Bikaverin

from Fusarium subglutinans, ≥98% (HPLC)

Sinónimos:

6,11-Dihydroxy-3,8-dimethoxy-1-methylbenzo[b]xanthene-7,10, 12-trione, Lycopersin, NSC 215139

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About This Item

Fórmula empírica (notación de Hill):
C20H14O8
Número de CAS:
33390-21-5
Peso molecular:
382.32
Código UNSPSC:
12352200
NACRES:
NA.77

origen biológico

Fusarium subglutinans

Nivel de calidad

200

Ensayo

≥98% (HPLC)

Formulario

powder

solubilidad

DMSO: 0.5 mg/mL (may require sonication and heating)
chloroform: 0.5 mg/mL
dichloromethane: 0.5 mg/mL

temp. de almacenamiento

−20°C

cadena SMILES

[o]1c2c([c](c4c1cc(cc4C)OC)=O)c(c3c(c2O)C(=O)C(=CC3=O)OC)O

InChI

1S/C20H14O8/c1-7-4-8(26-2)5-10-12(7)17(23)15-18(24)13-9(21)6-11(27-3)16(22)14(13)19(25)20(15)28-10/h4-6,24-25H,1-3H3

Clave InChI

ZOQMSOSJEWBMHP-UHFFFAOYSA-N

Categorías relacionadas

Acciones bioquímicas o fisiológicas

Bikaverin is a red pigment with a polyketide tetracyclic benzoxanthone structure. Bikaverin has an antibiotic activity against some protozoa and fungi and also inhibits Succinate- and NAD-linked respiration in rat mitochondria at 20 mg/mL. At higher concentrations (50 mg/mL) it acts as an oxidative phosphorylation uncoupling agent of tumor cells and isolated rat liver mitochondria. Bikaverin demonstrates antitumor activity on Erlich ascites carcinoma (EAC), leukemia and sarcoma cells.
Bikaverin is a red pigment with a polyketide tetracyclic benzoxanthone structure. Bikaverin has an antibiotic activity against some protozoa and fungi.

Reconstitución

Soluble in DMSO (0.5 mg/mL, may require sonication and heating). For further dilution, water based solutions can be used. Chloroform (0.5 mg/mL) and dichloromethane (0.5 mg/mL).

Pictogramas

Skull and crossbones
GHS06

Palabra de señalización

Danger

Frases de peligro

H301

Consejos de prudencia

P301 + P310

Clasificaciones de peligro

Acute Tox. 3 Oral

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

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
049M4040V
14181107
14130905
093M4034V
32130902

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Mayra Mendonça et al.
Food chemistry: X, 12, 100136-100136 (2021-10-19)
Microbial pigments have a distinguished potential for applications in food and pharmaceutical industries, stimulating the research in this field. The present study evaluated the ideal conditions for extracting bikaverin (red pigment) from the biomass of Fusarium oxysporum CCT7620. Among the
Roberto Rodríguez-Ortiz et al.
Applied microbiology and biotechnology, 85(6), 1991-2000 (2009-10-20)
The fungus Fusarium fujikuroi (Gibberella fujikuroi mating group C) exhibits a rich secondary metabolism that includes the synthesis of compounds of biotechnological interest, such as gibberellins, bikaverin, and carotenoids. The effect of the carbon source on their production was checked
Yoon-E Choi et al.
Mycologia, 100(5), 701-709 (2008-10-31)
Fusarium verticillioides (teleomorph Gibberella moniliformis) is an ascomycete known to produce a variety of secondary metabolites, including fumonisins, fusaric acid and bikaverin. These metabolites are synthesized when the fungus is under stress, notably nutrient limitations. To date we have limited
Alejandro F Estrada et al.
Fungal genetics and biology : FG & B, 45(5), 705-718 (2008-01-22)
The fungal proteins of the White Collar photoreceptor family, represented by WC-1 from Neurospora crassa, mediate the control by light of different biochemical and developmental processes, such as carotenogenesis or sporulation. Carotenoid biosynthesis is induced by light in the gibberellin-producing
A G Medentsev et al.
Prikladnaia biokhimiia i mikrobiologiia, 41(5), 573-577 (2005-10-26)
We studied biosynthesis of colored naphthoquinone metabolites by Fusarium decemcellulare, F. graminearum, and F. bulbigenum fungi. F. bulbigenum and F. graminearum synthesized bikaverin and aurofusarin, respectively, which depended on the conditions of cultivation. F. decemcellulare synthesized soluble extracellular naphthoquinones of
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