A vitamin A metabolite and RAR ligand
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all-trans Retinoic Acid

Item No. 11017

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
CAS Number
302-79-4
Synonyms
  • atRA
  • NSC 122578
  • NSC 122758
  • RA
  • Vitamin A Acid
Molecular Formula
C20H28O2
Formula Weight
300.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 0.5 mg/ml
λmax
350 nm
SMILES
CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C(O)=O)=C(C)CCC1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    all-trans Retinoic acid is a metabolite of vitamin A and a ligand for retinoic acid receptors (RARs) with IC50 values of 9, 3, and 10 nM for RARα, RARβ, and RARγ, respectively, in radioligand binding assays.1 It induces expression of a luciferase reporter in COS-7 cells expressing RARα, RARβ, or RARγ (EC50s = 169, 9, and 2 nM, respectively). all-trans Retinoic acid (17 nmol) reduces papilloma formation induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in mice.2 It reduces bile duct proliferation, hydroxyproline levels, and liver inflammation in a rat model of α-naphthylisothiocyanate-induced chronic cholestasis and reduces plasma levels of alkaline phosphatase and bile salts in the Mdr2-/- mouse model of cholestasis.3 all-trans Retinoic acid also reduces hepatic fat accumulation, triglycerides, body weight, and serum glucose levels in mice with Western diet-induced obesity.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Idrest, N., Marill, J., Flexor, M.A., et al. Activation of retinoic acid receptor-dependent transcription by all-trans-retinoic acid metabolites and isomers. The Journal of Biological Chemisty 277(25), 31491-31498 (2002).

    2. Verma, A.K., Slaga, T.J., Wertz, P.W., et al. Inhibition of skin tumor promotion by retinoic acid and its metabolite 5,6-epoxyretinoic acid. Cancer Res. 40(7), 2367-2371 (1980).

    3. Cai, S.Y., Mennone, A., Soroka, C.J., et al. All-trans-retinoic acid improves cholestasis in α-naphthylisothiocyanate-treated rats and Mdr2-/- mice. J. Pharmacol. Exp. Ther. 349(1), 94-98 (2014).

    4. Kim, S.C., Kim, C.K., Axe, D., et al. All-trans-retinoic acid ameliorates hepatic steatosis in mice by a novel transcriptional cascade. Hepatology 59(5), 1750-1760 (2014).

    Product Citations

    Chupp, D.P., Rivera, C.E., Zhou, Y., et al. A humanized mouse that mounts mature class-switched, hypermutated and neutralizing antibody responses. Nat. Immunol. 2024, 1489-1506 (2024).