[CAS NO. 302-79-4]  Retinoicacid

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PRODUCTS SPECIFICATIONS [302-79-4]

Catalog
HY-14649
Brand
MCE
CAS
302-79-4

DESCRIPTION [302-79-4]

Overview

MDLMFCD00001551
Molecular Weight300.44
Molecular FormulaC20H28O2
SMILESCC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C(O)=O)=C(C)CCC1

For research use only. We do not sell to patients.


Summary

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 IC 50 s of 14 nM for RARα/β/γ. Retinoic acid bind to PPARβ/δ with K d of 17 nM. Retinoic acid acts as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha.


IC50 & Target

PPARβ/δ

17 nM (Kd)

PPARα

103 nM (Kd)

PPARγ

178 nM (Kd)

Human Endogenous Metabolite


In Vitro

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) [1] .
Retinoic acid (RA) bound to PPARα and PPARγ with a low affinity demonstrated by K d values of 100-200 nM. In contrast, Retinoic acid associates with PPARβ/δ with a K d of 17 nM, revealing both high affinity and isotype selectivity [2] .
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 [3] .
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 [4] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.


Clinical Trial

NCT Number Sponsor Condition Start Date Phase
NCT00378365 Assistance Publique - Hôpitaux de Paris
Leukemia, Promyelocytic, Acute
October 2006 Phase 3

Appearance

Solid


Shipping

Room temperature in continental US; may vary elsewhere.


Storage

-20°C, sealed storage, away from moisture and light

* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)


Solvent & Solubility

In Vitro:

DMSO : 50 mg/mL ( 166.42 mM ; ultrasonic and warming and heat to 60°C)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.3285 mL 16.6423 mL 33.2845 mL
5 mM 0.6657 mL 3.3285 mL 6.6569 mL
10 mM 0.3328 mL 1.6642 mL 3.3285 mL
* Please refer to the solubility information to select the appropriate solvent.
In Vivo:
  • 1.

    Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

    Solubility: 2.5 mg/mL (8.32 mM); Suspended solution; Need ultrasonic and warming

  • 2.

    Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline)

    Solubility: ≥ 2.5 mg/mL (8.32 mM); Suspended solution

  • 3.

    Add each solvent one by one: 10% DMSO >> 90% corn oil

    Solubility: ≥ 2.5 mg/mL (8.32 mM); Clear solution

  • 4.

    Add each solvent one by one: 5% DMSO >> 40% PEG300 >> 5% Tween-80 >> 50% saline

    Solubility: 2.5 mg/mL (8.32 mM); Suspended solution; Need ultrasonic

  • 5.

    Add each solvent one by one: 5% DMSO >> 95% (20% SBE-β-CD in saline)

    Solubility: 2.5 mg/mL (8.32 mM); Suspended solution; Need ultrasonic

* All of the co-solvents are available by MCE.


Synonyms

Retinoic acid
Retinoic acid, all-trans-
Vitamin A acid
Tretinoin
trans-Retinoic acid
2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-
all-trans-Vitamin A acid
Vitamin A acid, all-trans-
Vitamin A1 acid, all-trans-
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
β-Retinoic acid
(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
all-trans-Tretinoin
all-(E)-Retinoic acid
Tretin M
all-trans-β-Retinoic acid
Ro 1-5488
Retin A
AGN 100335
Aberel
all-trans-Retinoic acid
Vesanoid
ATRA
Renova
Atragen
Vesnaroid
Epi-Aberel
Cordes Vas
Dermairol
Aknoten
Airol
NSC 122578
Eudyna
Retacnyl
NSC 122758