PHR1187

Tretinoin

Pharmaceutical Secondary Standard; Certified Reference Material

• 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/REAXYS Number: 2057223
• EC Number: 206-129-0
• MDL number: MFCD00001551
• UNSPSC Code: 41116107
• PubChem Substance ID: 329823197
• NACRES: NA.24

Properties

• grade: certified reference material; pharmaceutical secondary standard
• Quality Level: 300
• agency: traceable to Ph. Eur. T1850000; traceable to USP 1674004
• API family: tretinoin
• form: solid
• CofA: current certificate can be downloaded
• technique(s): HPLC: suitable; gas chromatography (GC): suitable
• mp: 180-181 °C (lit.)
• application(s): food and beverages
• format: neat
• storage temp.: -10 to -25°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)

Description

General description

Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to pharmacopeia primary standards. Tretinoin is a medication used for the treatment of severe cystic acne. The drug acts by regulating epithelial cell growth and differentiation, sebum production, collagen synthesis and keratinization of the skin.

Application

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Tretinoin may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations by chromatography techniques.

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 secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAB7354 in the slot below. This is an example certificate only and may not be the lot that you receive.

Safety Information

• pictograms: GHS07,GHS08,GHS09
• signalword: Danger
• hcodes: H302 - H315 - H360FD - H410
• pcodes: P202 - P264 - P273 - P301 + P312 - P302 + P352 - P308 + P313
• 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