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Merck

1674004

USP

Tretinoin

United States Pharmacopeia (USP) 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
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329751371
MDL number:
MFCD00001551
Beilstein/REAXYS Number:
2057223

Product Name

Tretinoin, United States Pharmacopeia (USP) Reference Standard

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+

SMILES string

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

InChI key

SHGAZHPCJJPHSC-YCNIQYBTSA-N

grade

pharmaceutical primary standard

API family

tretinoin

manufacturer/tradename

USP

mp

180-181 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

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

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Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Tretinoin USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Tretinoin Cream
  • Tretinoin Gel
  • Tretinoin Topical Solution
  • Isotretinoin
  • Isotretinoin Capsules
  • Acitretin

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.

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.

Other Notes

Sales restrictions may apply.

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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

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Certificates of Analysis (COA)

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Isotretinoin
United States Pharmacopeia, 49(3), 2457-2457 (2023)
Tretinoin Topical Solution
United States Pharmacopeia, 4479-4479 (2013)
Tretinoin
United States Pharmacopeia, 41(4), 4478-4478 (2020)
Acitretin
United States Pharmacopeia, 35(5), 85-85 (2020)
Bogdan Jakiela et al.
American journal of respiratory cell and molecular biology, 51(2), 229-241 (2014-03-05)
Human rhinoviruses (RVs) are a major cause of exacerbations in asthma and other chronic airway diseases. A characteristic feature of asthmatic epithelium is goblet cell metaplasia and mucus hypersecretion. Bronchial epithelium is also an important source of lipid mediators, including
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