All Photos(2)

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

application(s)

cell culture | mammalian: suitable

color

yellow

mp

180-181 °C (lit.)

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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Related Categories

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

Certificate of Origin

  1. What are the I.U. for Product R2625, Retinoic acid?

    This product is not characterized by the activity in I.U. The purity specification, however, is not less than 98% by HPLC.

  2. What is Product R2625, Retinoic acid soluble in?

    Retinoic Acid is soluble in DMSO at about 40 mg/ml.

  3. How should I store the solutions of Product R2625, Retinoic acid?

    Retinoic acid is sensitive to air and light. Solutions should be stored under argon gas, preferably as aliquots at -70°C.

  4. What is the shelf life of Product R2625, Retinoic acid?

    R2625 has a shelf-life of two years. Shelf-life dates are found on Specification sheet on our website.

  5. Why is Product R2625, Retinoic acid not shipped on dry ice?

    Dry ice is not necessary for shipment, since Product No. R2625 is stable to ship at ambient temperature for up to two weeks. Once received, it should be stored at -20°C.

  6. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  7. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Recovery from paralysis in adult rats using embryonic stem cells.
Deshpande DM et al.
Annals of Neurology, 60, 32-32 (2006)
Chang Yang et al.
Metallomics : integrated biometal science, 11(8), 1419-1429 (2019-07-18)
Antimony (Sb) belongs to the same group as arsenic (As) in the periodic table, and both share similar characteristics. However, Sb2O3 (SbIII) has no methylation capacity, unlike arsenic trioxide (As2O3). In the present study, we determined the effect of SbIII...
Lijun Ling et al.
AIDS (London, England), 33(4), F1-F12 (2019-03-05)
The combined combination antiretroviral therapy (cART) and anti-α4β7 RM-Act-1 antibody therapy allows macaques to durably control simian immunodeficiency virus (SIV) rebound after withdrawal of the interventions. Here, we aimed to investigate whether vedolizumab (VDZ), a clinical-grade humanized anti-α4β7 antibody, would...
Anna M Paczulla et al.
Nature, 572(7768), 254-259 (2019-07-19)
Patients with acute myeloid leukaemia (AML) often achieve remission after therapy, but subsequently die of relapse1 that is driven by chemotherapy-resistant leukaemic stem cells (LSCs)2,3. LSCs are defined by their capacity to initiate leukaemia in immunocompromised mice4. However, this precludes...
In vitro pancreas formation from Xenopus ectoderm treated with activin and retinoic acid.
Moriya N, et al.
Development, Growth & Differentiation, 42, 593-593 (2000)

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.

Protocols

Neural Stem Cell Culture Protocols

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

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