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Merck

R3255

Sigma-Aldrich

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
EC Number:
225-296-0
MDL number:
MFCD00079542
UNSPSC Code:
12352106
PubChem Substance ID:
24278676
NACRES:
NA.77

Key Documents

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Quality Level

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)

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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

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H319,H335,H360FD

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP7961
MKBV4966V
MKCB7022
WXBC3499V
WXBC3387

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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)
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
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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