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R3255

Sigma-Aldrich

13-cis-Retinoic acid

≥98% (HPLC)

Sinónimos:

Isotretinoin

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About This Item

Fórmula empírica (notación de Hill):
C20H28O2
Número de CAS:
4759-48-2
Peso molecular:
300.44
Número CE:
225-296-0
Número MDL:
MFCD00079542
Código UNSPSC:
12352106
ID de la sustancia en PubChem:
24278676
NACRES:
NA.77
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Nivel de calidad

200

Ensayo

≥98% (HPLC)

Formulario

powder

técnicas

HPLC: suitable

color

yellow to yellow-orange

mp

172-175 °C (lit.)

temp. de almacenamiento

−20°C

cadena SMILES

[H]\C(C(O)=O)=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C

InChI

1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-

Clave InChI

SHGAZHPCJJPHSC-XFYACQKRSA-N

Información sobre el gen

human ... NOS2(4843) , RARA(5914) , RARB(5915) , RARG(5916)

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Categorías relacionadas

Aplicación

13-cis-Retinoic acid has been used:
  • as a component of fresh media for LA-N-5 differentiation[1]
  • to treat medulloblastoma cells for cell differentiation[2]
  • to treat spheroids for generating time-lapse videos[3]
  • to examine its head- deforming activity under light and dark conditions in Xenopus laevis[4]

Acciones bioquímicas o fisiológicas

13-cis-Retinoic acid (RA) has anti-inflammatory and anti-tumor action. The action of RA is mediated through RAR-β and RAR-α receptors. RA attenuates iNOS expression and activity in cytokine-stimulated murine mesangial cells. It induces mitochondrial membrane permeability transition, observed as swelling and as a decrease in membrane potential, and stimulates the release of cytochrome c implicating mechanisms through the apoptosis pathway. These activities are reversed by EGTA and cyclosporin A. RA also increases MMP-1 protein expression partially via increased transcription.

Características y beneficios

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictogramas

Health hazardExclamation mark
GHS08,GHS07

Palabra de señalización

Danger

Frases de peligro

H315,H319,H335,H360FD

Clasificaciones de peligro

Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

Órganos de actuación

Respiratory system

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

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
WXBF1092V
MKCR6065
WXBD7939V
MKCP7961
MKBV4966V

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Si necesita una versión concreta, puede buscar un certificado específico por el número de lote.

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Visite la Librería de documentos

UAB30, a novel RXR agonist, decreases tumorigenesis and leptomeningeal disease in group 3 medulloblastoma patient-derived xenografts
Garner E F, et al.
Journal of Neuro-Oncology, 140(2), 209-224 (2018)
M P Rigobello et al.
Biochemical pharmacology, 58(4), 665-670 (1999-07-21)
Retinoic acids, structurally related to vitamin A, inhibit the in vitro proliferation of different types of normal and neoplastic cells. The effects of all-trans, 9-cis, and 13-cis retinoic acids were tested on mitochondria isolated from rat liver. All the compounds
Differential expression, distinct localization and opposite effect on Golgi structure and cell differentiation by a novel splice variant of human PRMT5
Sohail M , et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1853(10), 2444-2452 (2015)
Live multicellular tumor spheroid models for high-content imaging and screening in cancer drug discovery
Reid B G, et al.
Current Chemical Genomics and Translational Medicine, 8(Suppl-1), 27-27 (2014)
Induction of pronephric tubules by activin and retinoic acid in presumptive ectoderm of Xenopus laevis
Moriya N, et al.
Development, Growth & Differentiation, 35(2), 123-128 (1993)
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Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

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