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Tretinoin

United States Pharmacopeia (USP) Reference Standard

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Synonym(s):
Retinoic acid, ATRA, Tretinoin, Vitamin A acid, all-trans-Retinoic acid
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
302-79-4
Molecular Weight:
300.44
Beilstein:
2057223
MDL number:
MFCD00001551
PubChem Substance ID:
329751371
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

tretinoin

manufacturer/tradename

USP

mp

180-181 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

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.

Application

Tretinoin USP reference standard for use in specified quality tests and assays.

Also used to prepare standard, standard stock, system suitability and system suitability stock solutions for assay, identification and impurity analysis according to given below monographs of the United States Pharmacopeia (USP):
  • Tretinoin
  • Isotretinoin
  • Acitretin
  • Tretinoin Topical Solution

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.

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.  ​

Other Notes

Sales restrictions may apply.

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

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Acitretin
United States Pharmacopeia, 35(5), 85-85 (2020)
Isotretinoin
United States Pharmacopeia, 49(3), 2457-2457 (2023)
Tretinoin
United States Pharmacopeia, 41(4), 4478-4478 (2020)
Tretinoin Topical Solution
United States Pharmacopeia, 4479-4479 (2013)
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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