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1674004

USP

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:
Molecular Weight:
300.44
Beilstein/REAXYS Number:
2057223
MDL number:
PubChem Substance ID:
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

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1 of 4

This Item
T1850000PHR11871353500
vibrant-m

1674004

Tretinoin

vibrant-m

T1850000

Tretinoin

vibrant-m

PHR1187

Tretinoin

vibrant-m

1353500

Isotretinoin

manufacturer/tradename

USP

manufacturer/tradename

EDQM

manufacturer/tradename

-

manufacturer/tradename

USP

format

neat

format

neat

format

neat

format

neat

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

food and beverages

application(s)

pharmaceutical (small molecule)

API family

tretinoin

API family

tretinoin

API family

tretinoin

API family

isotretinoin

mp

180-181 °C (lit.)

mp

180-181 °C (lit.)

mp

180-181 °C (lit.)

mp

172-175 °C (lit.)

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.

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_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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Tretinoin
United States Pharmacopeia, 41(4), 4478-4478 (2020)
Isotretinoin
United States Pharmacopeia, 49(3), 2457-2457 (2023)
Tretinoin Topical Solution
United States Pharmacopeia, 4479-4479 (2013)
Acitretin
United States Pharmacopeia, 35(5), 85-85 (2020)
Juliana Gutierrez-Mazariegos et al.
Endocrinology, 155(11), 4275-4286 (2014-08-15)
Nuclear receptors are transcription factors that regulate networks of target genes in response to small molecules. There is a strong bias in our knowledge of these receptors because they were mainly characterized in classical model organisms, mostly vertebrates. Therefore, the

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