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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
Beilstein:
2057223
MDL number:
MFCD00001551
UNSPSC Code:
41116107
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, 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.

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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Biology of reproduction, 86(2), 35-35 (2011-11-15)
The requirement for vitamin A in reproduction and development was first determined from studies of nutritional deficiencies. Subsequent research has shown that embryonic development and both male and female reproduction are modulated by retinoic acid (RA), the active form of
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Development (Cambridge, England), 139(5), 843-858 (2012-02-10)
Retinoic acid (RA) is a vitamin A-derived, non-peptidic, small lipophilic molecule that acts as ligand for nuclear RA receptors (RARs), converting them from transcriptional repressors to activators. The distribution and levels of RA in embryonic tissues are tightly controlled by
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