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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
Yun Xia et al.
Nature cell biology, 15(12), 1507-1515 (2013-11-19)
Diseases affecting the kidney constitute a major health issue worldwide. Their incidence and poor prognosis affirm the urgent need for the development of new therapeutic strategies. Recently, differentiation of pluripotent cells to somatic lineages has emerged as a promising approach
Bhaskar Chanda et al.
Cell, 155(1), 215-227 (2013-10-01)
Hematopoietic stem cells (HSCs) develop from a specialized subpopulation of endothelial cells known as hemogenic endothelium (HE). Although the HE origin of HSCs is now well established in different species, the signaling pathways that control this transition remain poorly understood.
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