This product is soluble in chloroform (50 mg/ml). It is also reported to be soluble in DMSO (10 mM) and ethanol (25 mg/ml). Please see the link below to review the product data-sheet:
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/327/843/r4643pis.pdf
R4643
9-cis-Retinoic acid
≥98% (HPLC)
Synonym(s):
9-cis-Tretinoin, Alitretinoin
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1 MG
$87.00
About This Item
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
biological source
natural
Quality Level
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[1]
- as a medium component to study its effect on UDP-glucuronosyltransferases (UGT) expression in thyroid induced hepatocytes[2]
- to induce lymphangiogenesis in lymphatic endothelial cell[3]
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.[4] 9cRA is a potent agonist for retinoid X receptor (RXR) and retinoic acid receptor (RAR).[5] It has neurotrophic functionality, promotes neuronal differentiation and may have therapeutic potential in treating stroke.[6] It also regulates cytokine secretion and lymphocyte proliferation.[4] 9cRA favors the dopamine cells survival and induces neuroprotection in neurodegenerative disorder like parkinson′s disease.[7] It elicits anti-inflammatory function and stimulates mast cells and inhibits interleukin 4 and 5 expression levels.[8] 9cRA is in clinical trial phase II for treating refractory cancer.[5]
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
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
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Customers Also Viewed
9-cis retinoic acid induces neurorepair in stroke brain
Yu SJ, et al.
Scientific reports, 7(1), 4512-4512 (2017)
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
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)
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)
Articles
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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