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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:
Molecular Weight:
300.44
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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This Item
R2625P9417PHR1188
9-cis-Retinoic acid ≥98% (HPLC)

Sigma-Aldrich

R4643

9-cis-Retinoic acid

Retinoic acid ≥98% (HPLC), powder

Sigma-Aldrich

R2625

Retinoic acid

Palmitoleic acid ≥98.5% (GC), liquid

Sigma-Aldrich

P9417

Palmitoleic acid

Isotretinoin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1188

Isotretinoin

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98.5% (GC)

assay

-

form

powder

form

powder

form

liquid

form

-

technique(s)

HPLC: suitable

technique(s)

cell culture | mammalian: suitable

technique(s)

-

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

color

light yellow to yellow-orange

color

yellow

color

-

color

-

mp

189-190 °C

mp

180-181 °C (lit.)

mp

0.5 °C (lit.)

mp

172-175 °C (lit.)

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

Signal Word

Danger

Hazard Statements

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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  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

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Tretinoin United States Pharmacopeia (USP) Reference Standard

USP

1674004

Tretinoin

Isotretinoin European Pharmacopoeia (EP) Reference Standard

I0800000

Isotretinoin

Tretinoin European Pharmacopoeia (EP) Reference Standard

T1850000

Tretinoin

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)
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)
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)
9-cis-Retinoic acid (9cRA), a retinoid X receptor (RXR) ligand, exerts immunosuppressive effects on dendritic cells by RXR-dependent activation: inhibition of peroxisome proliferator-activated receptor gamma blocks some of the 9cRA activities, and precludes them to mature phenotype development
Zapata-Gonzalez F, et al.
Journal of Immunology, 178(10), 6130-6139 (2007)

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