Delta4-Dafachronic Acid

Delta4-Dafachronic acid is a racemic mixture of the sterol-derived hormones (25R)-Delta4-dafachronic acid and (25S)-Delta4-dafachronic acid, ligands of C. elegans nuclear hormone receptor family member DAF-12, a nucleoreceptor involved in dauer diapause, reproductive development, fat metabolism, and lifespan. Delta4-Dafachronic acid is an agonist of DAF-12 and a metabolite of cholesterol (Cay-9003100) in C. elegans. It induces transactivation of DAF-12 in NIH3T3 cells expressing the C. elegans or D. immitis receptor (EC50s = 81 and 0.65 nM, respectively). Delta4-Dafachronic acid induces molting of infective D. immitis (heartworm) third-stage larvae into L4 larvae, which is the first stage of the parasitic life cycle in dogs. It also induces the escape trajectory in embryos of the annual killifish A. limnaeus at 25°C, a condition that favors entrance into diapause, when used at a concentration of 75 µM.Formal Name: 3-oxo-cholest-4-en-26-oic acid. CAS Number: 23017-97-2. Synonyms: 3-keto-4-Cholestenoic Acid, Delta4-DA. Molecular Formula: C27H42O3. Formula Weight: 414.6. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 5 mg/ml, DMSO: 2.5 mg/ml, Ethanol: 12.5 mg/ml, Ethanol:PBS (pH 7.2) (1:10): 0.09 mg/ml. lambdamax: 241 nm. SMILES: O=C1CC[C@@]2(C)C(CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@@H]4[C@@H](CCCC(C)C(O)=O)C)=C1. InChi Code: InChI=1S/C27H42O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h16-18,21-24H,5-15H2,1-4H3,(H,29,30)/t17-,18?,21+,22-,23+,24+,26+,27-/m1/s1. InChi Key: PSXQJZDFWDKBIP-NNWQCNCGSA-N.