An internal standard for the quantification of Δ4-dafachronic acid
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Unlabeled Version(s)
14100Δ4-Dafachronic Acid
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Δ4-Dafachronic Acid-d3

Item No. 31009

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-oxo-cholest-4-en-26-oic-27,27,27-d3 acid
Synonyms
  • 3-keto-4-Cholestenoic Acid-d3
  • Δ4-DA-d3
Molecular Formula
C27H39D3O3
Formula Weight
417.6
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 2.5 mg/mlEthanol: 12.5 mg/mlEthanol:PBS (pH 7.2) (1:10): 0.09 mg/ml
λmax
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@]4([H])[C@@H](CCCC(C([2H])([2H])[2H])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/i2D3
InChi Key
PSXQJZDFWDKBIP-UMHCWJCBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $448

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    Product Description

    Δ4-Dafachronic acid-d3 is intended for use as an internal standard for the quantification of Δ4-dafachronic acid (Item No. 14100) by GC- or LC-MS. Δ4-Dafachronic acid is a racemic mixture of the sterol-derived hormones (25R)-Δ4-dafachronic acid and (25S)-Δ4-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.1,2 Δ4-Dafachronic acid is an agonist of DAF-12 and a metabolite of cholesterol (Item No. 9003100) in C. elegans.3,4 It induces transactivation of DAF-12 in NIH3T3 cells expressing the C. elegans or D. immitis receptor (EC50s = 81 and 0.65 nM, respectively).3 Δ4-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.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sharma, K.K., Wang, Z., Motola, D.L., et al. Synthesis and activity of dafachronic acid ligands for the C. elegans DAF-12 nuclear hormone receptor. Mol. Endocrinol. 23(5), 640-648 (2009).

    2. Motola, D.L., Cummins, C.L., Rottiers, V., et al. Identification of ligands for DAF-12 that govern dauer formation and reproduction in C. elegans. Cell 124(6), 1209-1223 (2006).

    3. Long, T., Alberich, M., André, F., et al. The development of the dog heartworm is highly sensitive to sterols which activate the orthologue of the nuclear receptor DAF-12. Sci. Rep. 10(1), 11207 (2020).

    4. Witting, M., Rudloff, H.-C., Thondamal, M., et al. Fast separation and quantification of steroid hormones Δ4- and Δ7-dafachronic acid in Caenorhabditis elegans. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 978-979, 118-121 (2015).

    5. Romney, A.L.T., Davis, E.M., Corona, M.M., et al. Temperature-dependent vitamin D signaling regulates developmental trajectory associated with diapause in an annual killifish. Proc. Natl. Acad. Sci. USA 115(50), 12763-12768 (2018).