Skip to Content
Merck

R4643

9-cis-Retinoic acid

≥98% (HPLC)

Synonym(s):

9-cis-Tretinoin, Alitretinoin

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
5300-03-8
Molecular Weight:
300.44
NACRES:
NA.77
PubChem Substance ID:
24899373
UNSPSC Code:
12352106
MDL number:
MFCD00270072

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

InChI key

SHGAZHPCJJPHSC-ZVCIMWCZSA-N

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+

biological source

natural

assay

≥98% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

light yellow to yellow-orange

mp

189-190 °C

storage temp.

−20°C

Quality Level

200

Gene Information

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

Related Categories

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

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SLBF3638V
120M5034V
120M5034
030M5028
028K5001

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
View All Related Papers

Articles

Discover Bioactive Small Molecules for Gene Regulation

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.

Related Content

Product Information Sheet - R4643
유전자 조절 연구를 위한 생체 활성 저분자

당사는 유전자 조절 연구 분야에서 표적 식별 및 검증을 위해 전사 인자 조절인자, 염색질 변형 효소 억제제, 작용제/길항제와 같은 여러 저분자 연구 툴을 제공합니다. 이러한 연구 툴 제품군은 아래에 나와 있습니다.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service