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Key Documents

R4643

Sigma-Aldrich

9-cis-Retinoic acid

≥98% (HPLC)

Synonyme(s) :

9-cis-Tretinoin, Alitretinoin

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About This Item

Formule empirique (notation de Hill):
C20H28O2
Numéro CAS:
Poids moléculaire :
300.44
Numéro MDL:
Code UNSPSC :
12352106
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Source biologique

natural

Niveau de qualité

Pureté

≥98% (HPLC)

Forme

powder

Technique(s)

HPLC: suitable

Couleur

light yellow to yellow-orange

Pf

189-190 °C

Température de stockage

−20°C

Chaîne SMILES 

CC1=C(\C=C\C(C)=C/C=C/C(C)=C/C(O)=O)C(C)(C)CCC1

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-ZVCIMWCZSA-N

Informations sur le gène

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Application

9-cis-Retinoic acid has been used:
  • as ligand for retinoid X receptor gamma (RXRγ) for inducing oligodendrocyte precursor cells differentiation and remyelination
  • as a medium component to study its effect on UDP-glucuronosyltransferases (UGT) expression in thyroid induced hepatocytes
  • to induce lymphangiogenesis in lymphatic endothelial cell

Actions biochimiques/physiologiques

9-cis-Retinoic acid (9cRA) is an isomer of all-trans-retinoic acid (ATRA), both of which are lipid molecules synthesized from a common precursor, vitamin A. 9cRA is a potent agonist for retinoid X receptor (RXR) and retinoic acid receptor (RAR). It has neurotrophic functionality, promotes neuronal differentiation and may have therapeutic potential in treating stroke. It also regulates cytokine secretion and lymphocyte proliferation. 9cRA favors the dopamine cells survival and induces neuroprotection in neurodegenerative disorder like parkinson′s disease. It elicits anti-inflammatory function and stimulates mast cells and inhibits interleukin 4 and 5 expression levels. 9cRA is in clinical trial phase II for treating refractory cancer.
Ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR) that act as transcription factors to regulate the growth and differentiation of normal and malignant cells.

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.
This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Conditionnement

Sealed ampule

Pictogrammes

Health hazardExclamation mark

Mention d'avertissement

Danger

Mentions de danger

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)

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Les clients ont également consulté

A phase I trial and pharmacokinetic study of 9-cis-retinoic acid (ALRT1057) in pediatric patients with refractory cancer: a joint pediatric oncology branch, national cancer institute, and children?s cancer group study
Adamson PC, et al.
Clinical Cancer Research, 7(10), 3034-3039 (2001)
9-cis-Retinoic acid regulation of four UGT isoforms in hepatocytes from rats with various thyroid states
Haberkorn V, et al.
Pharmaceutical Research, 20(10), 1568-1573 (2003)
Yanyan Zhan et al.
Nature chemical biology, 4(9), 548-556 (2008-08-12)
Nuclear orphan receptor Nur77 has important roles in many biological processes. However, a physiological ligand for Nur77 has not been identified. Here, we report that the octaketide cytosporone B (Csn-B) is a naturally occurring agonist for Nur77. Csn-B specifically binds
9-cis retinoic acid induces neurorepair in stroke brain
Yu SJ, et al.
Scientific reports, 7(1), 4512-4512 (2017)
Polysialylation at early stages of oligodendrocyte differentiation promotes myelin repair
Werneburg S, et al.
The Journal of Neuroscience, 37(34), 8131-8141 (2017)

Articles

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

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