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R2625

Sigma-Aldrich

Retinoic acid

≥98% (HPLC), powder

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

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

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This Item
PHR1187R464395144
Retinoic acid ≥98% (HPLC), powder

Sigma-Aldrich

R2625

Retinoic acid

-
Tretinoin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1187

Tretinoin

-
9-cis-Retinoic acid ≥98% (HPLC)

Sigma-Aldrich

R4643

9-cis-Retinoic acid

-
Retinol BioXtra, ≥97.5% (HPLC), ~3100 U/mg

Sigma-Aldrich

95144

Retinol

Premium Grade
form

powder

form

solid

form

powder

form

powder

technique(s)

cell culture | mammalian: suitable

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

HPLC: suitable

technique(s)

-

color

yellow

color

-

color

light yellow to yellow-orange

color

faint yellow to very dark yellow

solubility

chloroform: 50 mg/mL

solubility

-

solubility

-

solubility

-

storage temp.

−20°C

storage temp.

-10 to -25°C

storage temp.

−20°C

storage temp.

−20°C

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.

Signal Word

Danger

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

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25G
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Customers Also Viewed

Slide 1 of 9

1 of 9

In vitro pancreas formation from Xenopus ectoderm treated with activin and retinoic acid.
Moriya N, et al.
Development, Growth & Differentiation, 42, 593-593 (2000)
Retinoic acid induces multiple hallmarks of the prospermatogonia-to-spermatogonia transition in the neonatal mouse.
Busada JT et al.
Biology of Reproduction, 90, 64-64 (2014)
Sadman Sakib et al.
Biology of reproduction, 100(6), 1648-1660 (2019-03-31)
Three-dimensional (3D) organoids can serve as an in vitro platform to study cell-cell interactions, tissue development, and toxicology. Development of organoids with tissue architecture similar to testis in vivo has remained a challenge. Here, we present a microwell aggregation approach
Epigenetic regulation by RARa maintains ligand-independent transcriptional activity.
Laursen KB et al.
Nucleic Acids Research, 40, 102-102 (2012)
Recovery from paralysis in adult rats using embryonic stem cells.
Deshpande DM et al.
Annals of Neurology, 60, 32-32 (2006)

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Protocols

Neural Stem Cell Culture Protocols

Step-by-step culture protocols for neural stem cell culture including NSC isolation, expansion, differentiation and characterization.

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