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554720

trans-Retinoic Acid

Name: <i>trans</i>-Retinoic Acid
Brand: MM

Potent modulator of growth and differentiation. Inhibits melanocyte adhesion, motility, and growth.

Synonym(s):

trans-Retinoic Acid, Tretinoin, ATRA, Vitamin A Acid

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₂₈O₂

CAS Number:

302-79-4

Molecular Weight:

300.44

UNSPSC Code:

12352106

NACRES:

NA.21

MDL number:

MFCD00001551

Assay:

≥95% (by assay)

Form:

solid

Storage condition:

OK to freeze, desiccated (hygroscopic), protect from light

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Properties

description

Merck USA index - 14, 8165

Quality Segment

100

assay

≥95% (by assay)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, desiccated (hygroscopic), protect from light

color

yellow

solubility

DMSO: 25 mg/mL

shipped in

ambient

storage temp.

2-8°C

SMILES string

OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(CCCC1(C)C)C

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

Description

General description

Potent modulator of growth and differentiation. Exerts its effects by binding to nuclear retinoic acid receptors (RARs) which directly regulate gene expression. Inhibits melanocyte adhesion, motility, and growth. Has keratolytic activity. Induces differentiation of tumor cells of neural origin. Induces apoptosis in acute promyelocytic carcinoma cells. PROTECT FROM AIR.

Application

All-trans-retinoic acid modulates glycolysis via H19 and telomerase: the role of mir-let-7a in estrogen receptor-positive breast cancer cells.: This research reveals how all-trans-retinoic acid influences glycolysis in breast cancer cells by modulating H19 and telomerase, demonstrating its potential in breast cancer therapy (El Habre et al., 2024).

Retinoic acid tiers mitochondrial metabolism to Sertoli Cell-Mediated efferocytosis via a non-RAR-dependent mechanism.: The study explores the role of retinoic acid in linking mitochondrial metabolism to efferocytosis in Sertoli cells, providing insights into its non-RAR-dependent mechanisms and potential applications in reproductive biology (Wu et al., 2024).

Combined treatment of All-trans retinoic acid with Tamoxifen suppresses ovarian cancer.: This article discusses the synergistic effects of combining all-trans-retinoic acid with tamoxifen in suppressing ovarian cancer, highlighting a promising therapeutic strategy for ovarian cancer patients (Xu et al., 2024).

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, store in the refrigerator (4°C). DMSO stock solutions are stable for up to 2 weeks at 4°C.

Other Notes

Tosi, P., et al. 1994. Leuk. Lymphoma14, 503.
Clagett-Dame, M., et al. 1993. Arch. Biochem. Biophys.300, 684.
Labbaye, C., et al. 1993. Blood81, 475.
Sakashita, A., et al. 1993. Blood81, 1009.
Situ, R., et al. 1993. Dermatology186, 38.
Tini, M., et al. 1993. Genes Develop.7, 295.
Leid, M., et al. 1992. Trends Biochem. Sci.17, 427.
Sharpe, C.R. 1991. Neuron7, 239.
Thaller, C. and Eichele, G. 1990. Nature345, 815.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

pictograms

GHS08,GHS07,GHS09

signalword

Danger

hcodes

H302,H315,H360FD,H410

pcodes

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

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