R2625

Retinoic acid

≥98% (HPLC), powder

• Synonym(s): ATRA, Tretinoin, Vitamin A acid, 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

• biological source: synthetic (organic)
• Quality Level: 200
• 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.

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.

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