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Merck
CN

95152

Retinoic acid

≥98.0% (HPLC), ~3300 U/mg

Synonym(s):

ATRA, Tretinoin, Vitamin A acid, all-trans-Retinoic acid

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About This Item

Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
302-79-4
Molecular Weight:
300.44
EC Number:
206-129-0
UNSPSC Code:
12352203
MDL number:
MFCD00001551
Beilstein/REAXYS Number:
2057223

Key Documents

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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

SMILES string

CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C(O)=O)C(C)(C)CCC1

assay

≥98.0% (HPLC)

specific activity

~3300 U/mg

impurities

≤0.002% heavy metals

ign. residue

≤0.1% (as SO4)

loss

≤0.5% loss on drying

mp

180-181 °C (lit.), 182-186 °C

storage temp.

2-8°C

Gene Information

human ... RARA(5914), RARB(5915), RARG(5916)

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.
Ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR); primes embryonic stem cells to become neurons.

Other Notes

1 U corresponds to 1 international U acc. to Ph Eur II, 217 (1983)
Review: Retinoic acid metabolism

signalword

Danger

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

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Retinoic acid metabolism.
H F DeLuca
Federation proceedings, 38(11), 2519-2523 (1979-10-01)
Aliaksandr A Yarmishyn et al.
BMC genomics, 15 Suppl 9, S7-S7 (2014-12-19)
Long noncoding RNAs (lncRNAs) constitute a major, but poorly characterized part of human transcriptome. Recent evidence indicates that many lncRNAs are involved in cancer and can be used as predictive and prognostic biomarkers. Significant fraction of lncRNAs is represented on
Takehiro Takahashi et al.
Arthritis & rheumatology (Hoboken, N.J.), 67(1), 254-265 (2014-10-11)
Bleomycin-induced fibrosis and the tight skin (TSK/+) mouse are well-established experimental murine models of human systemic sclerosis (SSc). Growing evidence has demonstrated the pivotal role of Toll-like receptors (TLRs) in several autoimmune inflammatory diseases, including SSc. This study was undertaken
M Escamilla-Del-Arenal et al.
Molecular and cellular biology, 33(24), 5005-5020 (2013-10-23)
X chromosome inactivation is a remarkable example of chromosome-wide gene silencing and facultative heterochromatin formation. Numerous histone posttranslational modifications, including H3K9me2 and H3K27me3, accompany this process, although our understanding of the enzymes that lay down these marks and the factors
Joel Villalobos et al.
Investigative ophthalmology & visual science, 54(5), 3751-3762 (2013-04-25)
The safety of chronic implantation of a retinal prosthesis in the suprachoroidal space has not been established. This study aimed to determine the safety of a wide-field suprachoroidal electrode array following chronic implantation using histopathologic techniques and electroretinography. A platinum
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