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R4643

Sigma-Aldrich

9-cis-Retinoic acid

≥98% (HPLC)

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Synonym(s):
9-cis-Tretinoin, Alitretinoin
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
5300-03-8
Molecular Weight:
300.44
MDL number:
MFCD00270072
PubChem Substance ID:
24899373
NACRES:
NA.77

biological source

natural

Quality Level

200

Assay

≥98% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

light yellow to yellow-orange

mp

189-190 °C

storage temp.

−20°C

SMILES string

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+

InChI key

SHGAZHPCJJPHSC-ZVCIMWCZSA-N

Gene Information

human ... RARA(5914) , RARB(5915) , RARG(5916) , RXRA(6256) , RXRB(6257) , RXRG(6258)

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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

Biochem/physiol Actions

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.

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.
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.

Packaging

Sealed ampule

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Danger

Hazard Statements

H315 - H319 - H335 - H360

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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Anti-inflammatory effect of 9-cis retinoic acid on the human mast cell line, HMC-1
Lee JS and Kim IS
The Journal of Experimental Medicine, 13(2), 149-152 (2007)
Early post-treatment with 9-cis retinoic acid reduces neurodegeneration of dopaminergic neurons in a rat model of Parkinson?s disease
Yin LH, et al.
BMC Neuroscience, 13(1), 120-120 (2012)
Small Peptide Modulation of Fibroblast Growth Factor Receptor 3-Dependent Postnatal Lymphangiogenesis
Perrault DP, et al.
Lymphatic Research and Biology, 17(1), 19-29 (2019)
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)
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