R2625

Retinoic acid

≥98% (HPLC), powder

• Synonym(s): Vitamin A acid, ATRA, Tretinoin, all-trans-Retinoic acid
• Empirical Formula (Hill Notation): C₂₀H₂₈O₂
• CAS Number: 302-79-4
• Molecular Weight: 300.44
• Beilstein: 2057223
• EC Number: 206-129-0
• MDL number: MFCD00001551
• PubChem Substance ID: 24278674
• NACRES: NA.77

Properties

• Quality Level: 200
• 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
• Gene Information: human ... RARA(5914) , RARB(5915) , RARG(5916) , RXRA(6256) , RXRB(6257) , RXRG(6258) ; mouse ... Rara(19401) , Rarb(218772) , Rarg(19411) , Rxrb(20182)

Description

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.

Safety Information

• Pictograms: GHS07,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H302 - H315 - H360FD - H410
• Precautionary Statements: P202 - P264 - P273 - P301 + P312 - P302 + P352 - P308 + P313
• 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