R2625
Sigma

Retinoic acid

≥98% (HPLC), powder

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Synonym

all-trans-Retinoic acid

ATRA

Tretinoin

Vitamin A acid

Molecular Formula

C₂₀H₂₈O₂

Molecular Weight

300.44

CAS Number

302-79-4

Beilstein Registry Number

2057223

MDL number

MFCD00001551

PubChem Substance ID

24278674

EG/EC Number

206-129-0

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Descriptions

Frequently Asked Questions

Live Chat and Frequently Asked Questions are available for this Product.

Packaging

Sealed 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.

Properties

assay

≥98% (HPLC)

form

powder

color

yellow

180-181 °C(lit.)

Gene Information

human ... RARA(5914), RARB(5915), RARG(5916), RXRA(6256), RXRB(6257), RXRG(6258)

storage temp.

−20°C

References

Reference

Nadin, L., Participation of CYP2C8 in retinoic acid 4-hydroxylation in human hepatic microsomes. Biochem. Pharmacol. 58, 1201-1208, (1999)

Simoni, D., and Tolomeo, M., Retinoids, apoptosis and cancer. Curr. Pharm. Des. 7, 1823-1837, (2001)

Napoli, J.L., Biochemical pathways of retinoid transport, metabolism, and signal transduction. Clin. Immunol. Immunopathol. 80, S52-S62, (1996)

Sasai, Y., Generation of dopaminergic neurons from embryonic stem cells. J. Neurol. 249, II 41-II 44, (2002)

Merck

Merck 13,8251

Beilstein

Beil. 9,IV,2387

reference

Aldrich MSDS 1, 1587:C / Corp MSDS 1 (2), 3045:B / FT-IR 2 (1), 839:C / FT-IR 1 (1), 505:A / FT-NMR 1 (1), 790:A / IR-Spectra (3), 296:E / NMR-Reference 2 (1), 438:C / RegBook 1 (1), 553:J / Sax 6, 2364 / Sigma FT-IR 1 (2), 881:D / Structure Index 1, 84:C:4

Safety

Hazard Codes

Risk Statements

WGK Germany

RTECS

VH6475000

7-8-16-23