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R3255

13-cis-Retinoic acid

≥98% (HPLC)

Synonym(s):

Isotretinoin

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About This Item

Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
4759-48-2
Molecular Weight:
300.44
NACRES:
NA.77
PubChem Substance ID:
24278676
UNSPSC Code:
12352106
EC Number:
225-296-0
MDL number:
MFCD00079542
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Quality Segment

200

assay

≥98% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

yellow to yellow-orange

mp

172-175 °C (lit.)

storage temp.

−20°C

SMILES string

[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-

InChI key

SHGAZHPCJJPHSC-XFYACQKRSA-N

Gene Information

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

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

Biochem/physiol Actions

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.

Features and Benefits

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.

signalword

Danger

target_organs

Respiratory system

Storage Class

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Hazard Classifications

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

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