Retinoic acid-d5
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Retinoic acid-d5 is the the deuterium labeled Retinoic acid (HY-14649). Retinoic acid is a metabolite of vitamin A that plays important roles in cell growth, differentiation, and organogenesis. Retinoic acid is a natural agonist of RAR nuclear receptors, with IC50s of 14 nM for RARα/β/γ. Retinoic acid bind to PPARβ/δ with Kd of 17 nM. Retinoic acid acts as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha.
For research use only. We do not sell to patients.
- Purity: 99.1%
- CAS No.: 78996-15-3
- Formula: C20H23D5O2
- Molecular Weight:305.47
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Storage:
-80°C, protect from light, stored under nitrogen
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
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Biological Activity
Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs[1].
Retinoic acid (All-trans-retinoic acid, ATRA) is a highly potent derivative of vitamin A that is required for virtually all essential physiological processes and functions because of its involvement in transcriptional regulation of over 530 different genes. Retinoic acid exerts its actions by serving as an activating ligand of nuclear retinoic acid receptors (RARα-γ), which form heterodimers with retinoid X receptors (RXRα-γ)[2]. Retinoic acid (RA) bound to PPARα and PPARγ with a low affinity demonstrated by Kd values of 100-200 nM. In contrast, Retinoic acid associates with PPARβ/δ with a Kd of 17 nM, revealing both high affinity and isotype selectivity[3].Undifferentiated P19 cells express the Retinoic acid (RA) receptors RARα, RARβ, RARγ, and PPARβ/δ, as well as the Retinoic acid -binding proteins CRABP-II and FABP5. Induction of differentiation by treatment of cells with Retinoic acid results in transient up-regulation of CRABP-II and down-regulation of FABP5 that are observed at the level of both the respective proteins and mRNAs. Following the initial decrease, the level of both FABP5 protein and mRNA increases to attain a 2-2.5-fold higher level in mature neurons as compared with undifferentiated P19 cells. Induction of differentiation does not markedly affect the levels of either RARα or PPARβ/δ. The level of RARγ mRNA decreases by about 5-fold by day 4 and remained low in mature neurons[4].Retinoic acid (RA) is a morphogen derived from retinol (vitamin A) that plays important roles in cell growth, differentiation, and organogenesis. The Retinoic acid interacts with retinoic acid receptor (RAR) and retinoic acid X receptor (RXR) which then regulate the target gene expression[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
1. This compound can be used as a tracer
2. This compound can be used as an internal standard for quantitative analysis by NMR, GC-MS, or LC-MS.
Chemical Information
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CAS No. 78996-15-3
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Unlabeled Cas 302-79-4
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Appearance Solid
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Molecular Weight 305.47
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Formula C20H23D5O2
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Color Light yellow to yellow
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SMILES
O=C(O)/C=C(C)/C=C/C=C(C)/C=C/C1=C(C([2H])([2H])[2H])C([2H])([2H])CCC1(C)C
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Synonyms
Vitamin A acid-d5; all-trans-Retinoic acid-d5; ATRA-d5
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Shipping
Shipping with dry ice.
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Storage
-80°C, protect from light, stored under nitrogen
Solvent & Solubility
DMSO : 50 mg/mL (163.68 mM; ultrasonic and warming and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (273 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
References
[1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53(2):211-216. [Content Brief]
[2]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53(2):211-216. [Content Brief]
[3]. Wu L, et al. Retinoid X Receptor Agonists Upregulate Genes Responsible for the Biosynthesis of All-Trans-Retinoic Acid in Human Epidermis. PLoS One. 2016 Apr 14;11(4):e0153556. [Content Brief]
[4]. Shaw N, et al. Retinoic acid is a high affinity selective ligand for the peroxisome proliferator-activated receptor beta/delta. J Biol Chem. 2003 Oct 24;278(43):41589-92. [Content Brief]
[5]. Yu S, et al. Retinoic acid induces neurogenesis by activating both retinoic acid receptors (RARs) and peroxisomeproliferator-activated receptor β/δ (PPARβ/δ). J Biol Chem. 2012 Dec 7;287(50):42195-205. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 3.2736 mL | 16.3682 mL | 32.7364 mL | 81.8411 mL |
| 5 mM | 0.6547 mL | 3.2736 mL | 6.5473 mL | 16.3682 mL | |
| 10 mM | 0.3274 mL | 1.6368 mL | 3.2736 mL | 8.1841 mL | |
| 15 mM | 0.2182 mL | 1.0912 mL | 2.1824 mL | 5.4561 mL | |
| 20 mM | 0.1637 mL | 0.8184 mL | 1.6368 mL | 4.0921 mL | |
| 25 mM | 0.1309 mL | 0.6547 mL | 1.3095 mL | 3.2736 mL | |
| 30 mM | 0.1091 mL | 0.5456 mL | 1.0912 mL | 2.7280 mL | |
| 40 mM | 0.0818 mL | 0.4092 mL | 0.8184 mL | 2.0460 mL | |
| 50 mM | 0.0655 mL | 0.3274 mL | 0.6547 mL | 1.6368 mL | |
| 60 mM | 0.0546 mL | 0.2728 mL | 0.5456 mL | 1.3640 mL | |
| 80 mM | 0.0409 mL | 0.2046 mL | 0.4092 mL | 1.0230 mL | |
| 100 mM | 0.0327 mL | 0.1637 mL | 0.3274 mL | 0.8184 mL |
Retinoic acid-d5 Related Classifications
HY-14649S4 Related Classifications
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