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R2625

Sigma-Aldrich

Retinoic acid

≥98% (HPLC), powder, RAR and RXR ligand

Synonym(s):

ATRA, Tretinoin, Vitamin A acid, all-trans-Retinoic acid

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About This Item

Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
Beilstein:
2057223
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77

product name

Retinoic acid, ≥98% (HPLC), powder

biological source

synthetic (organic)

Quality Level

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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General description

Retinoic acid (RA), a retinoid, exerts a broad range of biological effects. It plays a role in regulating cellular differentiation and proliferation in both normal and transformed cells, potentially influencing oncogenes. All-trans retinoic acid (ATRA) is regarded as the most pertinent and functionally active metabolite of Vitamin-A. RA may serve as a type of signal molecule through a nuclear receptor to regulate regional differentiation in the central nervous system. Moreover, at a concentration of 1 nM (with maximal differentiation at 1 µM), RA induces morphological and functional terminal differentiation in a cell line of human promyelocyte leukemia, indicating its potential involvement in the differentiation of specific hematopoietic cells. Additionally, RA can indirectly impact neuronal differentiation by modifying the expression of neuronal cell surface receptors to peptide growth factors.

Furthermore, RA and other retinoids can also inhibit cellular proliferation and stimulate tyrosinase activity in a human melanoma cell line, while also inhibiting cell-substrate adhesion and motility in melanocytes. ATRA plays a vital role in the formation of the mammalian vascular system. Specifically, it regulates endothelial cell proliferation and vascular remodeling throughout tissue angiogenesis.

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.

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.

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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  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. 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.

  3. 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.

  4. 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.

  5. 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.

  6. 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.

  7. 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.

  8. 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. 

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

    Ask a Scientist here.

Retinoic acid induces multiple hallmarks of the prospermatogonia-to-spermatogonia transition in the neonatal mouse.
Busada JT et al.
Biology of Reproduction, 90, 64-64 (2014)
Epigenetic regulation by RARa maintains ligand-independent transcriptional activity.
Laursen KB et al.
Nucleic Acids Research, 40, 102-102 (2012)
Retinoic acid regulates both expression of the nerve growth factor receptor and sensitivity to nerve growth factor.
Scheibe RJ and Wagner JA
The Journal of Biological Chemistry, 267, 17611-17616 (1992)
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
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

Articles

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

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

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