R2625

Retinoic acid

≥98% (HPLC), powder

• Synonim(y): ATRA, Tretinoin, Vitamin A acid, all-trans-Retinoic acid
• Wzór empiryczny (zapis Hilla): C₂₀H₂₈O₂
• Numer CAS: 302-79-4
• Masa cząsteczkowa: 300.44
• Beilstein: 2057223
• Numer WE: 206-129-0
• Numer MDL: MFCD00001551
• Kod UNSPSC: 12352106
• Identyfikator substancji w PubChem: 24278674
• NACRES: NA.77

Właściwości

• pochodzenie biologiczne: synthetic (organic)
• Poziom jakości: 200
• Próba: ≥98% (HPLC)
• Postać: powder
• metody: cell culture | mammalian: suitable
• kolor: yellow
• mp: 180-181 °C (lit.)
• rozpuszczalność: chloroform: 50 mg/mL
• temp. przechowywania: −20°C
• ciąg SMILES: 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+
• Klucz InChI: SHGAZHPCJJPHSC-YCNIQYBTSA-N
• informacje o genach: human ... RARA(5914) , RARB(5915) , RARG(5916) , RXRA(6256) , RXRB(6257) , RXRG(6258) ; mouse ... Rara(19401) , Rarb(218772) , Rarg(19411) , Rxrb(20182)

Opis

Opis ogólny

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.

Zastosowanie

• 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.

Działania biochem./fizjol.

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.

Cechy i korzyści

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.

Inne uwagi

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

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Informacja o środkach bezpieczeństwa

• Piktogramy: GHS07,GHS08,GHS09
• Hasło ostrzegawcze: Danger
• Zwroty wskazujące rodzaj zagrożenia: H302 - H315 - H360FD - H410
• Zwroty wskazujące środki ostrożności: P202 - P264 - P273 - P301 + P312 - P302 + P352 - P308 + P313
• Klasyfikacja zagrożeń: Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - Skin Irrit. 2
• Kod klasy składowania: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Klasa zagrożenia wodnego (WGK): WGK 2
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable
• Środki ochrony indywidualnej: dust mask type N95 (US), Eyeshields, Gloves