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R2625

Sigma-Aldrich

Retinoic acid

≥98% (HPLC), powder

Synonym(s):
Vitamin A acid, ATRA, Tretinoin, all-trans-Retinoic acid
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
Beilstein:
2057223
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

powder

technique(s)

cell culture | mammalian: suitable

color

yellow

mp

180-181 °C (lit.)

solubility

chloroform: 50 mg/mL

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-YCNIQYBTSA-N

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Application

  • Retinoic acid (RA) has been used for the differentiation of embryonic stem cells into motor neurons.
  • It has been used for the differentiation of Xenopus ectoderm into pancreas.
  • It has also been used to study epigenetic regulation by RARα (retinoic acid receptor α).
  • It has been used to study RA signaling of prospermatogonia transition into spermatogonia.

Packaging

1, 5 g in ampule
50, 100, 500 mg in ampule

Biochem/physiol Actions

all−trans−Retinoic acid (ATRA) is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR). The bound RAR and RXR act as transcription factors that regulate the growth and differentiation of both normal and malignant cells. Cytochromes P450 (CYPs) catalyze the 4-hydroxylation of ATRA. Retinoic acid primes embryonic stem cells to become neurons.

Features and Benefits

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R2625.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - Skin Irrit. 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Articles

Derivation of Functional Oligodendrocyte Progenitor Cells (OPCs) from Human Neural Stem Cell Lines

Derivation and characterization of functional human neural stem cell derived oligodendrocyte progenitor cells (OPCs) that efficiently myelinate primary neurons in culture.

Retinoic Acid and Gene Expression

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.

Retinoic Acid and Gene Expression

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.

Protocols

Neural Stem Cell Culture Protocols

Step-by-step culture protocols for neural stem cell culture including NSC isolation, expansion, differentiation and characterization.

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