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T1850000

Tretinoin

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

Retinoic acid, 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
Beilstein:
2057223
MDL number:
MFCD00001551
UNSPSC Code:
41116107
PubChem Substance ID:
329826691
NACRES:
NA.24

biological source

synthetic

grade

pharmaceutical primary standard

Agency

EP

API family

tretinoin

form

solid

manufacturer/tradename

EDQM

technique(s)

gas chromatography (GC): suitable
liquid chromatography (LC): suitable

mp

180-181 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°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

Gene Information

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

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General description

This product is provided as delivered and specified by the issuing pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the authority of the issuing pharmacopoeia. For further information and support please go to the website of the issuing pharmacopoeia.

Tretinoin is a medication used to treat a variety of skin conditions such as photodamaged skin, acne, etc. It is used as an anti-aging product and also as an oral treatment for leukemia.

Application

This European Pharmacopoeia reference standard is intended for use only as specifically prescribed in the European Pharmacopoeia.

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.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Signal Word

Danger

Hazard Statements

H302,H315,H360FD,H410

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

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Tretinoin: The Active Retinoid Medication Used for Treatment of Acne Fast and Effectively (2019)
Rie Saba et al.
Developmental biology, 389(2), 173-181 (2014-03-01)
Germ cell sex is defined by factors derived from somatic cells. CYP26B1 is known to be a male sex-promoting factor that inactivates retinoic acid (RA) in somatic cells. In CYP26B1-null XY gonads, germ cells are exposed to a higher level
Enrico Garattini et al.
Cancer treatment reviews, 40(6), 739-749 (2014-02-01)
All-trans retinoic acid (ATRA) is the most important active metabolite of vitamin A controlling segmentation in the developing organism and the homeostasis of various tissues in the adult. ATRA as well as natural and synthetic derivatives, collectively known as retinoids
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
Mathilde Raverdeau et al.
Journal of immunology (Baltimore, Md. : 1950), 192(7), 2953-2958 (2014-03-25)
Retinoic acid (RA) is produced by a number of cell types, including macrophages and dendritic cells, which express retinal dehydrogenases that convert vitamin A to its main biologically active metabolite, all-trans RA. All-trans RA binds to its nuclear retinoic acid
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