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R3255

Sigma-Aldrich

13-cis-Retinoic acid

≥98% (HPLC)

Synonyme(s) :

Isotretinoin

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About This Item

Formule empirique (notation de Hill):
C20H28O2
Numéro CAS:
4759-48-2
Poids moléculaire :
300.44
Numéro CE :
225-296-0
Numéro MDL:
MFCD00079542
Code UNSPSC :
12352106
ID de substance PubChem :
24278676
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

powder

Technique(s)

HPLC: suitable

Couleur

yellow to yellow-orange

Pf

172-175 °C (lit.)

Température de stockage

−20°C

Chaîne 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-

Clé InChI

SHGAZHPCJJPHSC-XFYACQKRSA-N

Informations sur le gène

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

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Application

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H315,H319,H335,H360FD

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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9-cis-Retinal vitamin A analog

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trans-Retinoic Acid Potent modulator of growth and differentiation. Inhibits melanocyte adhesion, motility, and growth.

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Acide rétinoïque United States Pharmacopeia (USP) Reference Standard

USP

1674004

Acide rétinoïque

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)
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)
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)
Raoud Marayati et al.
Translational oncology, 14(1), 100893-100893 (2020-10-04)
Retinoic acid (RA) therapy has been utilized as maintenance therapy for high-risk neuroblastoma, but over half of patients treated with RA relapse. Neuroblastoma stem cell-like cancer cells (SCLCCs) are a subpopulation of cells characterized by the expression of the cell
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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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